“Evidence-based” has become one of the most trusted labels in social services. A program runs a randomized controlled trial, shows strong results, and becomes the safe choice for governments and funders trying to spend limited dollars on what works. The trouble starts when that one result gets treated as permanent.

Caroline Whistler has spent the last 15 years at Third Sector, the organization she co-founded to help state and local governments deliver more responsive services. She works with government partners, communities, local philanthropies and employers to agree on the outcomes that matter and adapt the evidence to local conditions. Her recent piece in SSIR made the case that the evidence-based movement is more complicated than the sector likes to admit.

She has no interest in throwing the evidence out. Starting from what has worked somewhere is essential, and the scientific method is good at forcing clarity on a hypothesis and the outcomes you want. What it leaves out is room to learn. A trial is a snapshot of one place at one moment, while people and communities keep changing. Nurse Family Partnership is her clearest example: a program with strong trial results whose effects declined over the years, funded in a way that rewarded sticking to the approved model and left no space to ask why families were dropping out.

The obstacles she sees are mostly structural: contracts that won’t pay providers who change anything, and data extracted for compliance reports and rarely returned to the people who could learn from it.

For executive directors, the work starts with asking who a program isn’t working for. For funders, it means paying for learning organizations as well as strong programs, and sometimes for changing the conditions around them. Caroline’s case is for discipline around the process of learning over loyalty to any single program model, and for building real relationships with the civil servants who hold many of the keys to better outcomes.

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Episode Highlights:

[00:01:50] What “evidence-based” actually means
[00:03:20] How evidence-based became a federal policy priority
[00:05:35] Why a randomized controlled trial is only a snapshot
[00:08:20] The myth of the permanently proven program
[00:09:25] Nurse Family Partnership and the results that faded over time
[00:12:05] What the scientific method gets right, and what it misses
[00:15:55] Why evidence alone is not enough, but essential
[00:18:20] Contracts that punish providers for adapting
[00:19:25] Data as a one-way street
[00:22:40] Questions every executive director can start asking now
[00:24:15] How funders can invest in learning and changing conditions
[00:26:30] Where trust-based philanthropy fits with evidence
[00:33:35] Why nonprofits need relationships with civil servants

Notable Quotes:

[00:08:50] “It’s like a prescription pill that you can take and adopt everywhere else. And when it comes to people and human services, you just have to keep measuring.” Caroline Whistler

[00:13:45] “What communities ultimately want is not an evidence-based practice, they want better lives.” Caroline Whistler

[00:16:00] “Evidence alone is not enough, but it is essential.” Caroline Whistler

[00:17:00] “There’s no set it and forget it or, oh, this works somewhere else. We can assume it will work here. People are complicated, the world changes.” Caroline Whistler

[00:28:15] “The incorrect interpretation of trust-based philanthropy is that it’s all about just vibes and trust and that there is no room for evidence.” Eric Ressler

[00:33:15] “We can do better work if we center outcomes over centering programs.” Caroline Whistler

Resources & Links:

• Third Sector — Caroline’s organization, helping governments deliver more responsive, outcomes-focused services

• When Evidence Isn’t Enough: Caroline Whistler’s recent SSIR article on the evidence-based movement — mentioned at [00:00:45]

• Trust-Based Philanthropy Project — the approach discussed at [00:25:55]

• Designing Tomorrow J&E episode on the scientific method and design thinking — mentioned at [00:10:50]

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:00:40]: Caroline, welcome to the show.

Caroline Whistler [00:00:45]: Thanks for having me.

Eric Ressler [00:00:45]: Yes, I’m so excited for this day. So backing up, the reason that you’re here today is because you penned an article in SSIR basically talking about how a movement towards evidence-based work is a little bit more complex than we’ve all been giving it credit for. Before we get into all that though, can you give our listeners just a little bit of background around yourself, who you are, the work that you’ve been doing, how you got to this point of penning this article?

Caroline Whistler [00:01:15]: For sure. So I live out in California with my family, and for the past 15 years I have been working at, co-founded, and have been in the work with an organization called Third Sector, helping our governments to deliver more responsive services to communities. The way we do that is by showing up with our state and local government partners, with the communities they serve, with local philanthropies and employers to align on outcomes that matter, look at the evidence as to what works, and then think about how to adapt that to get to ongoing better outcomes and improvements for their own constituents and their communities.

Eric Ressler [00:01:55]: Okay. I want to start with a really fundamental basic question. What does it actually mean to be evidence-based? Is there some kind of certification you get for that? What does that term actually mean? Who determines whether or not something is evidence-based? Let’s just start there.

Caroline Whistler [00:02:05]: Oh gosh, it’s a great question. So there’s an academic version of evidence-based, which shows have you set up a rigorous evaluation, with the gold standard being a randomized control trial. But basically, have you created conditions to evaluate, usually with some folks who get an intervention and some folks who don’t, and did you rigorously evaluate and try to isolate what exactly about the intervention made a difference in somebody’s life? And then have you codified that and have you been able to replicate that in other places? So evidence-based, at least for social services, social sector work, can often mean having a program plan, an intervention plan, and then rigorously testing that by giving some folks that intervention and some not to see if it works at achieving the intended outcome goal.

Eric Ressler [00:03:05]: And the goal of that being to assess and evaluate if an intervention is actually effective or not.

Caroline Whistler [00:03:10]: For sure. Yeah. We all want to find what works because certainly whether it’s our governments or our communities, we want to figure out what works and do more of those things with our taxpayer dollars or the limited time we have.

Eric Ressler [00:03:25]: Yeah. Okay. I love that definition, it tracks, it makes sense. And my sense, just being in the sector and observing it, is that maybe 10 years ago, five years ago, there was this peak evidence-based moment. It was this term that you would see: oh, this is an evidence-based intervention or an evidence-based program. What’s your sense around what led to that? Do you agree that that was around the timeframe that happened? Do you feel like it’s growing? What’s the state of this and what led to this becoming more central in the dialogue in the space?

Caroline Whistler [00:04:00]: Yeah, I think certainly around 10 years ago, or even in the early 2000s, it really became a policy goal. Whether it was the George W. Bush administration or the Obama administration, there was a real focus on funding what works, evidence-based practices. And that focus at the federal level around codifying and defining what an evidence-based practice is, and investing federal dollars in those, I think really contributed to a lot of organizations trying to do that evaluation work to get certified as evidence-based so they could tap into a large amount of that public funding. So that’s the history of it. And I would say the current state is that we still have a strong desire to invest in evidence. You see recent policy changes with Workforce Pell, setting clear outcome goals, job placement, wage increases, new acts in Congress, the Evidence-Based Grant Making Act and others. So it’s certainly not going away. It’s growing and is certainly a big part of the federal policy and state and local policy conversation today.

Eric Ressler [00:05:10]: So taking this idea of evidence-based work at its core in good faith seems to make a lot of sense. It’s like, hey, we want to make sure that especially when the government, but even when donors are investing in interventions and we’re trying to do social good work and public good work that has high stakes, we want to make sure what we’re doing works. What, in your opinion, are we getting wrong about that approach, or how is it actually a lot more complicated than it sounds?

Caroline Whistler [00:05:35]: So first, I fully agree. We want to invest in what works. We want to find what works. We want to do more of those things. One of the things I’ve noticed after the past 15 years working with state and local governments trying to replicate some of those evidence-based practices is that context really matters. Doing the randomized control trial or getting that signature of evidence is oftentimes like a snapshot or a photo of: yes, you were able to achieve those goals in this place. But it doesn’t necessarily translate to different contexts, or sometimes the world changes, for example. So I would say what we’re getting right is this idea that we need to figure out what works. That is the right north star. We need to figure out what’s going to work to keep homeless people housed, what’s going to work to help people get employed at high wages.

And I think what has been harder to grapple with, particularly from a government and policy perspective, is the prescriptive way that policymaking happens around evidence, where they take that one snapshot of: great, someone got a great result. We did the randomized control trial in Texas. Now we’re going to write that up as a law and make sure that all 50 states have to do a program in that specific way. And this idea that prescriptions can lead to outcomes, I think that’s where we’ve fallen short a little bit, because we’re not acknowledging that the context really matters, the world changes, people are complicated, and a program that might have worked really well for certain people in a certain context may not translate to other places or forever more into the future, particularly with social programs where the interventions are often behavioral as well.

Eric Ressler [00:07:15]: Yeah. So to me, I see how this starts to get complicated pretty quickly, because a couple different things are going through my mind. One, this idea even of doing randomized controlled trials where humans are the subjects is thorny. When you think an intervention might work and you’re intentionally only giving that intervention to some part of the population, knowing that the other part of the population is not getting it. Now, I assume in most of these trials they’re getting other interventions or the gold standard of what was done before, but walk me through how policymakers and folks behind these interventions grapple with that.

Caroline Whistler [00:07:55]: Yeah, so oftentimes policymakers, well, I would say they’re not necessarily running the RCTs, but they are taking the information they get from those snapshots. So they’re encouraging philanthropy or nonprofits to do those experimentations, and then based on the results, they’ll say, “Oh, that worked well. Maybe we can take that as a policy, and we won’t require you to keep evaluating it because you’ve already gotten that gold standard once.”

Eric Ressler [00:08:20]: Interesting.

Caroline Whistler [00:08:25]: But really, the challenge is, yes, there are absolutely challenges in the evaluations around whether you’re denying services, this and the other. But I think the broader challenge is this idea that once you achieve that positive result in evidence, the assumption is that you will forever achieve that result, and that we need to stop measuring, or we don’t need to measure, because you’ve got the gold standard.

Eric Ressler [00:08:45]: It’s been proven. It’s proven forever now.

Caroline Whistler [00:08:50]: It’s like a prescription pill that you can take and adopt everywhere else. And when it comes to people and human services, you just have to keep measuring, because we’ve seen across the country that, unfortunately, strong evidence-based programs might not achieve the same results in different places if there are different conditions there.

Eric Ressler [00:09:10]: So do you have an example or a story or a case study of where an evidence-based intervention maybe worked in one place, and they tried the copy-paste, prescription-style approach somewhere else and it was not as successful?

Caroline Whistler [00:09:25]: Yeah, so a couple of examples. One that I like: there was a very strong, very large federally funded program called Nurse Family Partnership. They did a lot of randomized control trials in different places over time and saw strong results in terms of keeping moms in the program, reducing preterm births, et cetera. They got those RCTs and ended up using them to secure a lot of public funding. But as the years went on, folks were noticing that the nurses in these programs were doing the program in the same way, but they weren’t retaining families in the same way, and they were actually getting different outcomes and results. Rather than having space to be curious and say, “What’s going on? What could we do to change the program?” the way the funding worked, there wasn’t really space for that curiosity.

The funding was based on “Are you doing the program as it was approved and defined in this evidence-based study?” versus “Are you learning what’s going on in the context and thinking about adapting this evidence-based program to what it takes to get to results for these particular communities?” And so that was a case where they actually saw the effects, even in randomized control trials, decrease over time for a program that had very strong effects and evidence, and they decreased as the world changed and the context changed.

Eric Ressler [00:10:55]: So I think this is a good segue. Jonathan and I actually just recently did an episode about what in our sector we should and can take from the scientific method, and what we should take and maybe leave from design thinking methodologies. And what I’m hearing is that this evidence-based approach is borrowing a lot from the traditional scientific method, having randomized controlled trials, et cetera. And the shortcoming is maybe where we might be able to leverage some of what I think design thinking is so good at, which is acknowledging that these problems are wicked and difficult to put a blanket over and say every problem like this is going to work the same way, and instead being much more willing to lean into the unknown and into the specific circumstances of any given community. So how do you think about those different frameworks, if at all, and what does a more forward-looking evidence-based approach look like in your mind?

Caroline Whistler [00:12:05]: I would agree that a lot of our social science work is based on a more traditional evidence-based approach from the hard sciences, if you will. What that really gets right is having a strong hypothesis and clarity of the outcomes that you want to achieve, which I think is really important for every community that wants to improve people’s lives: to get clear on how you want to improve people’s lives, what that would look like, and be very explicit about that. What we have learned is not enough with that scientific method is really being able to build in the space for that learning, for understanding context, and that learning and improvement. Because if you think about it, and we work with state and local governments, their goal is to deliver results for their communities, not one day, not next week, but on an ongoing basis. And in order to do that, you actually need a feedback loop around the work that you’re doing. How are you listening to the folks that are receiving the services? How are you learning about who this is working for and who it’s not working for? What are the other conditions going on in our community right now that may or may not be affecting the outcomes here? And then how are you taking that in and adapting the service delivery model or the programmatic intervention to respond to those conditions? The scientific method is great for setting out the hypothesis, great for setting out the clarity around that initial stake in the ground to try, but a lot of times the evaluation structure doesn’t allow for the responsiveness or the learning that our communities need, because what they ultimately want is not an evidence-based practice, they want better lives. They want results for their communities. So that’s a little bit of the difference.

And design thinking has been really helpful for a lot of our public sector partners, helping them understand what it means to listen to their communities: that it’s not an info session, that it could look more like an ongoing body and more of a co-governance approach to thinking about what our goals are and how we align our resources. Design thinking has also been helpful to adopt a test-and-learn approach a little more quickly. Public systems, state and local governments, are pretty risk averse. Test and learn is kind of scary, whereas going with an off-the-shelf evidence-based approach may feel safer and maybe more defensible, even if it doesn’t actually get the same results for your community members.

Eric Ressler [00:14:45]: And I could imagine that the people behind those decisions, of course they want the best outcomes for their community. And also, they want to make sure they’re making a smart, trusted choice. So if they see a gold standard evidence-based program that looks like it has the right shape, why wouldn’t they reach for that? And they might even think, “We don’t need to do tests. We already have a sense of what is right here, so we’re going to go for that intervention.” What I’m hearing you say, though, is that just having an evidence-based mark on any given intervention is not really enough, unless the conditions are close enough that you can make a good judgment and say, “Hey, we’re pretty confident. Although this evidence-based program wasn’t run in this exact community at this exact time, there’s enough of the same shape of this problem that it’s probably going to work.” But I do wonder, if you are in that position, how should you evaluate reaching for an existing evidence-based program versus building your own set of experiments with more of a design thinking methodology?

Caroline Whistler [00:15:55]: Well, again, it all starts with what you want to achieve. And our recommendation is that evidence alone is not enough, but it is essential. So say you want to increase stable housing or reduce recidivism for a population. If those are your community goals and you’ve gotten specific about for whom, our first stop is always to look at the existing evidence. What are the existing services that have actually been shown anywhere to make a difference? Let’s start there. This is not “let’s throw spaghetti at the wall” or create something totally new. There’s been enough work done in the social sciences that you should always start with the evidence base that is there. Use that to help build the hypothesis, informed by your providers, your community members, your particular context. And then the most critical piece is that it’s not “look through the library and pick the one that feels best.” It’s look through the library, pick the ones that feel the most resonant, build the model that you think has the best chance of working, and then you have to measure. You can’t get out of the measurement side.

There’s no set it and forget it or, oh, this works somewhere else. We can assume it will work here. People are complicated, the world changes. So the biggest piece is how you build the infrastructure around evidence so you can understand what the conditions are in your community and what’s working. A big part of that infrastructure is setting the goals and seeing what success would look like. What’s your data and measurement plan? How are you going to collect that data, talk about it, look at it, and make changes as you go to ensure you’ve got the greatest chance of hitting those outcomes, using the existing evidence base and your local context?

Eric Ressler [00:17:40]: So in your experience, where is this process falling apart? Because when I hear you outline it like that, it makes really good logical sense. Hey, if we have a problem, the first thing we’re going to do is look and see how other people solved it and draw inspiration, if not heavy inspiration, from that. Then we’re going to implement it, see if it worked, measure, and iterate from there. That seems like a very logical approach to doing this work, but that’s often not what happens. So what are some of the main scenarios or flavors you see where that ideal process falls apart?

Caroline Whistler [00:18:20]: Yeah, so there are a couple of structural pieces that make it difficult. One is actually around contracting. We do a lot of work around outcomes funding, helping communities set those outcome goals and processes, and give providers flexibility to build off an evidence-based practice and adapt it. Many communities don’t have that flexibility. Or for many governments, it’s “No, no, no, we’re going to prescribe.” They’ll say you’ve got these outcome measures or metrics, and oftentimes they’re outputs, and in a cost reimbursement way they describe, “You must do X, Y, Z to achieve these goals.” So essentially they’re tying providers’ hands behind their backs: yes, we’re going to try to measure on an ongoing basis, but we’re not going to let you change anything.

Eric Ressler [00:19:00]: Yeah, that’s the purpose.

Caroline Whistler [00:19:05]: Yeah. Well, we won’t pay you if you change something. You can change something, but we won’t pay you. So some of those payment incentives are structurally what prevent ongoing learning from happening. Another thing is data: data quality, and data for learning and improvement. I think this is a known problem for a lot of state and local governments. Data is a one-way street. They extract it from providers and communities in reports for compliance purposes, and they’re not necessarily talking about it, looking at it, seeing how they can learn and improve. So it’s easy to say that you want to use data for learning and improvement. Sometimes the right data’s not getting collected, or providers and communities don’t have access to that data until after a contract is done, so they can’t even know how they’re doing or how they could improve. Some of those hurdles, like the legal ones, need to be myth-busted a little bit, but there are processes and standard operating procedures that need to change within our state and local governments to make the data more integrated and more available to governments and communities, so they can do the sense-making and the changing to see if their evidence-based programs are working.

Eric Ressler [00:20:30]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

So what I’m hearing is that there are oftentimes structural issues with how the contract, so to speak, or even literally the contract between the provider and the government or the funder, is set up. And we see this in the philanthropic space too, with non-government funders: how foundations or even major individual donors are sometimes asking boots-on-the-ground providers to report back and gather data, or maybe there’s a grant for the intervention but no budget allocated to measurement and evaluation. Or even if there is budget, it’s more of a retrospective or a postmortem, and there’s no room for feedback and iteration cycles. So that’s one big flavor of that. I’m sure there are others, but I actually want to ask: if a listener is an executive director or one of the implementers of these interventions, maybe a program officer, whatever, what can be done about this? How can we empower our listeners to take some of this learning and say, “This sounds great. We should change these things. That’s a long-term project. I have to deliver next month for my constituents. What can we do in the seat, so to speak?”

Caroline Whistler [00:22:45]: So depending on what seat you’re in, I think it starts by making these implicit challenges explicit. Let’s start from the executive director of a nonprofit side. You’re implementing an evidence-based program. Ask the questions: How am I using data? Do I have access to data? If I do not, how am I going to my funder to say, “This is a problem. We need access to this data for ongoing learning”? If I do have access to data on the outcomes and measures that matter, how am I using it? How are we talking about it as a team? How are we talking about it with our communities and our other key stakeholders to influence our decision-making? So I would start there. And some of the questions you could ask are: Who is my program not working for, and what might we learn about that? What are some of the conditions or things going on outside of our one program that might be influencing the intended outcomes for an individual? That could surface some really fertile ground to then have specific conversations with your funders, your local governments, and your key stakeholders about what in the conditions or the infrastructure might need to change to make your evidence-based practice and your intervention more successful. Who might you need to be in relationship with? How might you need to approach this problem differently as a broader ecosystem outside of your one nonprofit?

Putting on the funder hat, I would say think about how to support not just a strong program, but learning organizations. So being able to provide some of that flexible funding to say, “Yes, I’m curious if your program worked this year with these people, but also, what are you learning about the contours of your program, or the things that are changing in the environment, about where you’re most successful and why?” Investing in that type of learning is really important. Also, as a funder, you have the opportunity to invest in programs, but you can also invest in changing the conditions that might help make your program and others more successful. For example, I mentioned some of the structural issues around how nonprofits get paid, which can influence the type of work they’re able to do to learn and adapt. As a funder, if nonprofits are contracting with the government, you could provide support to help that government shift how it actually pays nonprofits. California actually did this a couple of years ago. Funders supported advocacy to change the payment terms, because California was paying long after services were delivered and nonprofits couldn’t metabolize that. So that’s changing a structural condition that can help both build evidence and support the learning and improvement needed to make sure you’re achieving those outcomes on the ground for folks.

Eric Ressler [00:25:55]: I want to zag away from this theme just a little bit into something I’m curious about. There’s this rigorous evidence-based argument, especially around funding and interventions. And coexisting with that is this idea of trust-based philanthropy. I don’t think those things are at odds with one another, but I do wonder what we should be taking from both of those. My sense is that the best-case scenario is that there’s some Venn diagram there, and the overlap is what we should be aiming for, but I’d love to hear your take on that.

Caroline Whistler [00:26:30]: I love that idea, actually, of bringing more of trust-based philanthropy into the room, because what we’ve noticed in our work is that trying to get to better outcomes in your community, whether that’s for homelessness, workforce development, et cetera, is a systems change effort. You need the interventions and you need the structural change. You also need the relational change, and trust-based philanthropy fits in there, as well as shifts in mental models around: wait a minute, what is our community about? What is our government for? What are the roles of each of the players in our community to get to better outcomes? So I think trust-based philanthropy plays a pretty critical role in modeling for government and other players what it looks like to anchor on a shared vision and shared north star outcomes, and to give some flexibility on the program side for folks to adapt and learn. In my mind, that still means holding that north star and measuring towards the outcomes and metrics that matter, but giving programmatic flexibility that often does not exist in our public systems right now because it’s scary. It feels like, “Whoa, we’re not sure exactly what they’ll do.” But I think trust-based philanthropy can be a real model for other players in the ecosystem of what it looks like to be in relationship with those proximate to the problem, define with them the goals you’re looking for, and then trust them to adapt the evidence-based practices, while holding those north stars clear and measuring and evaluating towards them over time. So I’m glad you brought that up. That’s a really interesting connection.

Eric Ressler [00:28:10]: Yeah. My sense is that the incorrect interpretation of trust-based philanthropy is that it’s all about just vibes and trust and that there is no room for evidence, or that evidence is counterproductive to that modality, which I don’t think is the intention behind trust-based philanthropy. And talking more about some of these structural issues, what I see often in my work is that the orgs critical to running these interventions are not set up to be sustainable in and of themselves. Funding streams in for a particular program, salaries are set, and often salaries and all overhead costs are set by the funder. There’s this balance between flexibility and rigor, and I think both can coexist. To me, that’s the spirit of what trust-based philanthropy is pointing to: we need to, like you said, co-design with communities and trust the implementers who are closest to the problem, instead of a more hierarchical, top-down approach where all of the power and oversight, and the dynamics of that power and oversight, come down from the funder. When we talk about relationships and doing this work in the best of faith, we need to find a balance between evidence and trust and experimentation and rigor. In my opinion, when you look at the best, most successful interventions, however they did it and whatever methodology they attached to, those are some of the ingredients that are integral to interventions actually working.

Caroline Whistler [00:29:55]: Yeah. The one addition I would have to that is that we’ve noticed that having rigor around the process of learning and improvement is really important: codifying that rigor in setting your outcome goals, what that looks like, and how you’re going to measure it, but also the rigor of process in what we’re learning, how we’re making adjustments, who this is working for and who it isn’t. That’s not a programmatic requirement per se, but it’s a process requirement. If you’re a people-serving organization or a people-serving government, you need to be committed to continuing to be responsive, to continuing to get feedback from those who are experiencing your services, and using it, talking about it with relevant stakeholders in your agency and across agencies, and using it to learn and improve. As I’ve gone through this work, I keep thinking, gosh, if we can have more of that discipline on the process versus fidelity to a particular program model, I think that might help our communities, and certainly our local governments, be more responsive to the communities they serve.

Eric Ressler [00:31:10]: I love that. Are you familiar with the term kaizen? Do you know that term?

Caroline Whistler [00:31:10]: Yes.

Eric Ressler [00:31:10]: Yeah. Kaizen, for our listeners who might not be familiar, is a Japanese term. I hope I don’t butcher the exact definition, but it essentially means continuous learning. It’s one of our values at Cosmic. It’s actually one of the few values at Cosmic I can remember based on what’s on our website. But it’s so true to how we need to approach these problems that are so dynamic, so fluid, ever-changing, because they are systemic in nature. Culture is always moving. The nature of the problems and the environments of those problems are always in flux. So it’s obvious on the surface that we need to constantly be improving and learning and measuring. And it’s interesting to hear your perspective and experience around where that breaks down. Because my sense is that almost everyone in the space would resonate with that. Of course we need to continuously learn and improve and measure, but there are all these constraints or barriers or bottlenecks that make that impractical, because of the structure that’s set up, or the circumstances, or the funding, or a combination of all of those things. So to me, conversations like this are so important to have, in hopes that they will influence the people who have the ability to change those systems at a meta level, whether that’s you as a program officer at a major foundation or someone in government who’s in charge of getting this money out the door, thinking about how policy happens. I feel like this is one of the most important things the sector needs to continuously be thinking about. So I appreciate you coming to the studio and breaking down some of your thinking. Before we wrap up, Caroline, is there anything you would recommend folks listen to or follow outside of this podcast? How can people get in touch? Plug your work away at this point.

Caroline Whistler [00:33:00]: Well, I’ve appreciated this time to talk about the evidence-based movement as more of an evolution of where we need to go with continuous improvement, versus a throw-it-out revolution. We’ve done good work. We can do better work if we center outcomes over centering programs. So big fan of that. A couple of other things: you can check out the work Third Sector has been doing on our website, www.thirdsectorcap.org. But my bigger call to folks would be to be in community with your civil servants and your public systems. I come from the nonprofit sector, and I also do a lot of work in philanthropy, and it’s not always the case that those folks are in community with their local county, state, or even city civil servants who may be working on very similar issues. So my call to action is this: our state and local governments are often the largest or one of the largest co-funders of social services and of the change we want to see in communities. Engage with them and build relationships with them, because they hold the keys to a lot of the structural and relational change that needs to happen in order to unlock better outcomes for our communities over the long haul. So that’s my call to action there.

Eric Ressler [00:34:30]: I love that. I think that’s a beautiful place to wrap up. Thank you so much for your time today, Caroline.

Caroline Whistler [00:34:35]: Thank you, Eric.

Eric Ressler [00:34:35]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Lately almost every nonprofit email in my inbox reads like an emergency, with a match deadline at midnight or a warning that the work stops if I don’t give today.

Some of those deadlines are real. Most are manufactured, and supporters can feel the difference. Each frantic appeal might raise a little more this week, and each one also spends down the trust we’ll need when something truly urgent happens. The sector has been crying wolf for years, and people have noticed.

The same pressure shows up inside our organizations. Hustle culture borrowed from startups, Slack messages flagged urgent that could have waited a week, and now AI convincing leaders that two months of work should take two days. I saw this up close working with startups in the Bay Area, and it produced burnt-out teams doing their worst work.

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Speed still matters to me. I want ideas tested quickly so we can learn from them. Speed is a culture you build with sprints, rest and clear priorities. Urgency is a tone, and when it never switches off, people stop believing it.

Jonathan is heading into a capital campaign at the Seymour Center and chose to raise in small bursts while he builds. That lets him walk into donor meetings with an invitation to something ambitious and honestly say the organization is fine. I’d take that position over a guilt trip every time.

So treat urgency like a line in your budget. Decide how much you can afford to spend this year, and where. When you overspend it, your supporters, your team and you are the ones who pay.

Episode Highlights:

[00:00:30] Why fake urgency is spreading through the social impact sector
[00:01:20] Burnout, donor fatigue and the cost of always sounding frantic
[00:04:55] What real urgency looks like: policy windows, funding cuts, sudden departures
[00:05:45] The boy who cried wolf problem in fundraising
[00:08:10] Urgent for you, or urgent for your audience?
[00:08:50] The urgency budget
[00:09:40] How funders reward “new” over proven
[00:11:15] Hustle culture, 996 and AI-driven speed expectations
[00:14:20] The opposite problem: bureaucracy and organizational malaise
[00:19:10] Speed and urgency are different things
[00:22:25] Raising in small bursts and fundraising from a position of strength
[00:27:50] “Your lack of planning is not my emergency”

Notable Quotes:

[00:04:20] “You can be really ambitious and work on really ambitious work, but do it calmly, do it patiently, do it with a kind of self-regulation as an organization.” Eric Ressler

[00:08:20] “Is this urgent for you as the worker working on this or is this urgent for your audience? And I think more often than not, the answer to that, those are different.” Jonathan Hicken

[00:08:55] “You basically have an urgency allotment for the year. How are you going to spend it and where?” Eric Ressler

[00:26:35]: “False urgency is putting an emotional burden on your audience that just isn’t fair to do. I almost feel like it should be a sector faux pas.” Jonathan Hicken

[00:21:10] “Speed is kind of a culture and urgency is kind of a tone.” Eric Ressler

[00:29:55] “We need to build that trust and that relationship with our donor base, whatever that looks like, and that’s first. That has to be first.” Jonathan Hicken

Resources & Links:

• Cosmic: Eric’s creative agency for nonprofits and mission-driven organizations

• Seymour Marine Discovery Center: where Jonathan is Executive Director

• 996 working hour system: the 9am to 9pm, six-days-a-week schedule referenced at [00:12:15]

• What to Take and Leave From Design Thinking and the Scientific Method: mentioned at [00:19:25]

• Designing Tomorrow’s article on the ask/give ratio: mentioned at [00:07:25]

P.S. Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:00]: All right, Jonathan, got a meaty one for today. I want to talk today about this balance, I would say maybe even this imbalance that we have in the space, this confusion maybe even between ambition and urgency. And actually I’m going to go ahead and say fake urgency because I think that’s mostly the flavor of urgency that I see in the space.

Jonathan Hicken [00:00:20]: Whoa. Okay, let’s go. Coming out hot.

Eric Ressler [00:00:30]: All right, so here’s what’s driving this for me. I think this shows up at all levels. I think it shows up in terms of our communications, right? Everything’s urgent, everything’s chaotic, everything’s on fire. I think it shows up internally, right? Oh, the team, you got to be faster, move faster. I think AI is starting to create this expectation that things that used to take months should take days instead, which I think is mostly bullshit.

I think there’s also something that happens at the personal level when that’s the environment. And I think there is this cultural set and setting that’s creating this faster, faster, everything all at once communications and all the channels. And it’s starting to infect our sector and I don’t like it. I think we should change it.

Jonathan Hicken [00:01:15]: What are the impacts that you’re seeing of this?

Eric Ressler [00:01:20]: I think the impacts, again, thinking about all the levels, we talk a lot about burnout in this space. I think a lot of the burnout in this space is actually directly or indirectly related to this. So I think that’s one big thing. I think on the flip side, we’re eroding our trust and our credibility with the people that we need to actually make our missions happen. That’s a big problem.

So when you think about donor fatigue and donor trust, I don’t think the fatigue and the trust is broken because we’re sending too many emails. I think the fatigue and trust is breaking because we’re not being real with the people that we need to support our work. And I don’t think we’re doing ourselves a service or a support as a service if every email from us feels like it’s either urgent or a crisis all the time because it starts to make us look frantic, unorganized, and not serious as leaders and as organizations.

So those are just some of the top line impacts, but I think it goes deeper than that.

Jonathan Hicken [00:02:15]: I see this in the environmental space quite a bit and something I’ve been thinking about a lot where we believe, I believe that climate change and all that is an important problem to solve. And every time there’s a storm, every time there’s a fire, we all get up in arms like this is the sign that this is the end of the world. We got to solve this now. We got to go, go, go.

And even as someone who believes this is an important problem to solve, I see that and I’m like, I think this is doing damage to the environmental movement broadly when every single storm and every single fire is wrapped in this existential crisis that I feel like we’re losing our audience because we’re putting some of this maybe false urgency on it or asserting that this ambition is something that needs to be enacted right now.

Eric Ressler [00:03:10]: Yes. So that’s exactly it. You just hit the nail on the head, which is that you can be highly ambitious and do that work even if the issue is urgent without a fake sense of urgency or a manufactured urgency or an urgency everywhere all at once all the time, vibe. I’ll just use vibe as a placeholder word. And I think that is exactly it because scientifically, objectively, the climate crisis is an urgent crisis. Is every email you send about that crisis urgent?

Jonathan Hicken [00:03:45]: Yeah.

Eric Ressler [00:03:50]: No. It just isn’t, man. Even for an issue like that. And then when you think about the spectrum of issues where we’re all trying to fight for attention and there’s advice out there and maybe even some of our advice has been around how you have to create an urgency around the work. And I think there’s a balance there. If your work seems important, but something that could be put off, it is going to be hard to get attention and to get support.

So I think this really does come down to balance at the end of the day, but I think there’s a huge confusion in the space between ambition and urgency because I think you can be really ambitious and work on really ambitious work, but do it calmly, do it patiently, do it with a kind of self-regulation as an organization. And I think that it goes again both ways in terms of how you communicate externally and how you run the shop internally.

And my argument at the end of the day is that you will actually meet your mission faster if you move without fake urgency than if you move with fake urgency.

Jonathan Hicken [00:04:50]: So what does, let’s call it genuine ambition look like in contrast with this false urgency?

Eric Ressler [00:05:00]: So I think every org will actually have moments of true urgency. When there is a policy window that’s open, when funding gets cut unexpectedly, which happened to a lot of orgs in the last year. So I want to have some compassion for that. These are just a couple examples. When a leader unexpectedly quits, there are genuine moments of urgency that you can act on and that you should act on.

So I think the distinction is, think about this, do you have a friend who every single time they need something, it’s urgent, it must be done right away? And it’s just to the point where it’s just like, okay, every time I hear from this person, there’s some emergency that I need to come in and help with.

Jonathan Hicken [00:05:45]: Yeah, it’s a boy who cried wolf.

Eric Ressler [00:05:45]: Yeah. It’s exactly the boy who cried wolf. So there’s this short-termism in the space, especially around fundraising, especially in the political space, but it’s infecting the broader social impact space around all that matters is how much each email raises for us. And we’re willing to trade the short-term wins for the long-term credibility. And it’s a bad, dangerous game. And I believe we’re already seeing and have already seen the negative impacts of that in the political world and it is coming for the social impact sector.

Jonathan Hicken [00:06:20]: It makes sense because if we’re putting out all these urgent calls and people respond and then a year passes, two years pass, however long, and then there’s certainly going to be a moment of like, well, where are we now? Did we solve that thing? And I think especially when we put this false urgency on these really big problems that actually can’t be solved in a sprint, then what we’re communicating with the supporters who did show up is like, “Hey, you actually can’t take our call for urgency very seriously.”

Eric Ressler [00:06:55]: Exactly right. Yeah. And I think that’s the takeaway that people have. And then they’re just like, “Every time these folks email me, they’re asking for money.” And I’m not saying you shouldn’t make appeals in your communications. You absolutely need to, but there’s a way to do that that’s respectful. You need to be, first of all, authentic in your communication. If you’re communicating urgently, is it actually urgent? Ask yourself, is this actually urgent? Because most things are not actually urgent.

And are we creating value and/or signs and stories of progress alongside asking this ask give ratio that we’ve talked about before? And I think the best orgs that I follow who really follow more of a brand building approach and less of what we used to describe and still do to a degree as more of a transactional or performance marketing approach, I think it comes down to what you measure.

Are you measuring the effectiveness and the conversion rate of every single email only, or are you also measuring sentiment and donor trust and supporter trust and the overall lived experience of your supporters and the relationship that you’re building with them? I think you need to measure both.

Jonathan Hicken [00:08:10]: You pose this question, is this actually urgent as something that we should ask ourselves when we’re sending out communications? And I think there’s a little nuance in that, which is, is this urgent for you as the worker working on this or is this urgent for your audience? And I think more often than not, the answer to that, those are different.

Eric Ressler [00:08:30]: Those are often different.

Jonathan Hicken [00:08:35]: So you have to be careful because I might think, I might feel just in my job that this email is urgent, getting this fundraising campaign done is urgent, but is it urgent to the people who are giving in the same way it is for me?

Eric Ressler [00:08:50]: I think a really simple way to think about this, if you’re a leader or in charge of comms or whatever, since we’re talking about that part right now, is that you basically have an urgency allotment for the year.

How are you going to spend it and where? Are you going to take that urgency and are you going to spread it across every single communication? Well, then the impact of each of those urgent asks is going to be basically minuscule, if not meaningless. Maybe it works the first time, but it pretty quickly goes off a cliff. Whereas if you’re an org that is acting more patiently and more regulated, I’ll just use the word, and then there’s three or four or one or whatever the right number might be for your org, urgent request, it’s going to have an outsized impact because it’s going to be an outlier in how people are used to hearing from you the same way you would think about it in a human relationship.

Jonathan Hicken [00:09:40]: Funders have a responsibility in this conversation. And the reason I bring that up is actually just using an example from the Seymour Center. We have some educational programs that have existed for decades and proven to be impactful. I have found it difficult to get foundations to support these long-term successful programs. And what they tell me is we’re looking for something new. And so that motivates me to create something new, to get that funded, even though the thing that I’m trying to build may not be as successful as the thing I already have.

And that creates an environment in which we are incented to create these new programs, create these new initiatives, maybe even in some cases create new nonprofits to meet this funder desire to fund the next new thing. And so I think that there’s this cycle, and I think the trust degrades also, because I’ve also heard in my realm that some donors are losing trust in this sector that I operate in because so many things have started up and died that they approach certain new projects with skepticism. So there’s also this almost like this...

Eric Ressler [00:10:55]: You’re getting squeezed on both ends.

Jonathan Hicken [00:11:00]: You’re getting squeezed on both ends. And so I feel like funders also have a responsibility to be asking these same questions when a new program or a new initiative or a new nonprofit is coming in front of them: is this false urgency to solve a problem that could be solved with something that comes from that genuine ambition?

Eric Ressler [00:11:20]: Let’s talk a little bit about how this trickles down into the internal culture and dynamics because I think that’s an equally... I see this as moving both ways. So I think there’s also a broader culture of we must move fast, we must break things. We don’t want to be perceived as being slow or overly bureaucratic. And don’t get me wrong, there are orgs that have the opposite problem. Trust me, I’ve worked with some of them, but it sets this tone working at an organization.

I remember this distinctly from our early years as an agency working with startups in the Bay, in the valley, and everything was urgent. Every single week you were behind was a week your competitor was ahead. And it creates this hustle culture. And it’s so ironic because it’s the worst way to do anything effectively. Now, don’t get me wrong, there’s times to sprint, there’s times to grind, yes.

But if that is the norm, even more recently there was the, what was it, the 996 thing where the startups in Silicon Valley were expecting people to work nine hour days, six days a week.

Jonathan Hicken [00:12:25]: Yeah. Some CEO put that out as like, this should be the baseline expectation.

Eric Ressler [00:12:30]: So what I want our sector and our leaders to be careful of is this fake urgency is not just a communications problem. It is an internal culture and organizational planning problem too when it’s like, well, this needs to be done faster. We need to do it quicker. We need to do it cheaper. It’s a race to the bottom, man. And what it does is it forces leaders to burn out. It forces staff and team members to burn out and people produce their worst work.

Again, maybe you have an allotment every year. We’re going to sprint four times a year when we really need to, right? But our standard, our baseline is going to be one of calm and intention and sustainability and we’re going to be regulated. Hey, if it’s not urgent, I’m not going to say it’s urgent. If it’s not urgent, maybe I’m not going to write you on Slack. I’m going to write you an email or wait till the next time we have an email.

It really does come down to these almost micro interactions that set the tone and the tonality of what does it feel like to work here? And that’s something I’ve been thinking a lot about over the years, but especially recently, I do think AI is coming in and resetting what speed means. And I think we are trading speed for effectiveness and quality in a way that, I’m already seeing people starting to realize this is a problem. And I’m even reflecting on how we make sure at Cosmic and for our clients and on behalf of our clients that we don’t fall into those traps of like, oh, well now we can do what used to take two months in a week and it’s done.

But then objectively, is it really? Is it better? Is it done or does it now require a month and a half of cleanup because you built it with AI and it’s not actually solving the problem?

Jonathan Hicken [00:14:20]: I want to paint the picture of the other end of the spectrum, maybe even going into not enough urgency, just to unpack a little bit for listeners to diagnose where their own organizations are at. In your mind, what is the opposite of what you’ve just described?

Eric Ressler [00:14:40]: I think the opposite of, and I’ve seen this, so again, this is a spectrum and there’s a balance here. I think the opposite is every decision is painstakingly reviewed, discussed in depth, second guessed, to the point where it feels like getting anything done is like pushing a boulder through molasses. That creates an opposite problem, which is an organizational malaise where it’s just like, God, everything’s just so slow here. What’s even the point?

Jonathan Hicken [00:15:15]: Nothing moves.

Eric Ressler [00:15:15]: Nothing moves. There’s no point of even trying to move anything because it’s just so bureaucratic, right? We’ve definitely worked with orgs where, academia can be like this at times, which I’m sure you’ve experienced. Government can be like this at times and nonprofits can too, especially bigger orgs can suffer from this where there’s hierarchy upon hierarchy of decision makers, no one has autonomy, decisions get belabored to the point where by the time the decision’s made, it’s not even relevant anymore. It’s just like, oh great, we got to sign off on that thing that’s completely irrelevant now. So glad that happened.

Jonathan Hicken [00:15:55]: And on the communication side, a lack of urgency on communication would just be not communicating or being vague in your communications, not being direct if you’re making an ask.

Eric Ressler [00:16:05]: Or not jumping on the times where there’s real urgency, when there is a policy window or there is an opportunity that isn’t common and you’re not primed to act on it in a way that’s real and authentic and appropriate. So again, I’m not saying you should never act urgently. I’m saying we have to be careful about how we use our urgency, both in terms of our messaging and our internal culture building.

Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative and digital experiences.

Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:17:20]: The exercise going through my head is, in my role as executive director, when do I turn on the urgency? What are the signals? What am I looking for that causes me to go there? You’ve given a couple examples already for policy related organizations, for example. I don’t deal with that as much. So I’m like, what are some of the triggers that would cause me to say this is time to turn up the volume on the urgency versus, hey, we can sit on this particular project for a little bit, let it bake a little longer.

Eric Ressler [00:17:55]: Yeah. So I would say, and I’ll even say the way that I think about this is, is this a business critical problem? So for us, I have a number in mind around how many weeks of runway I want to have booked. And when that number dips below a certain signal, it’s an urgent problem and I’m going to act urgently to fix it, which means I’m going to turn off some of the activities that are longer term and turn on more of the survival mechanisms that I know I need to do to close business to keep the shop running.

On a nonprofit side, it may be a fundraising goal and this is a trap because you could always and should always be aiming to raise more and more and more. And if that’s your default state, this is the exact way you get onto the hamster wheel of fake urgency.

Jonathan Hicken [00:18:40]: Yeah. It begs the question of, you got to push, right? You got to push at some point, especially if you’re a new executive director or something. You got to get in, you got to make an impact, you got to make change. And so you’re incented to find that urgency and to act on it.

Eric Ressler [00:19:00]: Yes.

Jonathan Hicken [00:19:00]: And so it begs the question of how do I avoid getting sucked in, going too far basically?

Eric Ressler [00:19:10]: So I think another important distinction related to this is the distinction between speed and urgency because they are different things that I think often also get conflated. So what I will argue for is speed. And what I mean by that is, we recently did an episode around applying the scientific method and design thinking to social impact work. I want ideas tested quickly. So that’s speed, right? I want to go from idea to prototype and test as quickly as we possibly can so that we can get out of the overintellectualizing pondering mode and into the testing and learning mode.

So you can act quickly, but without urgency and especially without fake urgency in that moment. So you’re doing your work at a clip that builds momentum. And maybe the word to think about is how do we actually build sustained momentum? And the momentum’s never going to be perfectly stable, but you want the waves to be relatively stable with some big spikes and then maybe some dips when you’re taking vacation or taking time off as a team or as individuals.

Jonathan Hicken [00:20:15]: This is an interesting distinction between speed and urgency there. And it makes me wonder, again, how can I identify that for myself? And some ideas coming to mind are, it’s how I communicate.

Eric Ressler [00:20:30]: Yes.

Jonathan Hicken [00:20:30]: It’s when I communicate. It’s with whom I communicate. A lot of it comes down to these, as you alluded a little earlier, these micro interactions. Am I sending the signal that we’re all going to burn to the ground if we don’t move quickly versus defining, hey, we’re going to move quickly because we’re trying to get to this end state or make some decision. We’re going to get there. We’re good. Everybody, we’re good. We need to do the work.

Eric Ressler [00:20:55]: Yes.

Jonathan Hicken [00:21:00]: But hey, be confident. We’re going to eventually get there and we’ll be fine. I don’t know. I’m unpacking...

Eric Ressler [00:21:05]: No, I think you’re right on, man. And I’m reflecting on, speed is kind of a culture and urgency is kind of a tone. And you see why it’s easy to conflate those things. I actually think we’ve built at Cosmic a culture of speed. We’re fast and we move quickly, but we also have systems for pressure release in that. Some examples, we run sprints, we literally call them sprints, and we work a four-day work week, so we have that recoup time so it can be sustained.

And we know when things need to be done quickly with speed, and we know when things need time for reflection and space. So when we think about our creative work, when we think about naming, for example, you can’t speed run a naming process. You can, but it’s a really bad idea. Even just logistically, you got to do a trademark search on a name. It takes time.

And at the same time, there are certain things where we’re also not the agency that’s going to go do a six month research project and come back with a 200-page deck before we put pen to paper on anything. Hopefully that gives a little bit of clarity around the difference between speed and urgency. And again, this comes back from our founding and our principles around design being in our blood and design thinking specifically around getting ideas to test as soon as we can.

Jonathan Hicken [00:22:30]: It’s funny because I’ve actually been thinking about this, not in these exact terms, for a situation I’m dealing with right now as it relates to fundraising, where I have this choice. We have some money saved up for a capital investment here, which would basically do some new exhibits and stuff, and I have enough to get started already. This is a scalable project, so I could get this really high and go huge, or I could start moving right now as part of this experimentation, this let’s ship it, let’s test it, let’s move, let’s build as we go. Now, I could stop and I could raise as much as possible between now and an almost infinite amount of time.

Eric Ressler [00:23:15]: Sure.

Jonathan Hicken [00:23:15]: What I’m choosing to do instead is to raise little bits, little bursts to push it as we go. It’s almost like our minimum viable strategy in a way where I’m going to ship stuff and test it and keep building on it. Now that changes the tone of the conversation with the donors that I’m going to be approaching here in four weeks or so, because an urgent conversation with these donors would be like, “We need this now. If we don’t get this now, then we’re not going to be able to do this project and it’s on you.” It’s almost like a guilt trip in a way, which is what urgent fundraising creates, right? It’s almost like a sense of guilt.

Eric Ressler [00:23:55]: Or responsibility or...

Jonathan Hicken [00:23:55]: Yeah. Which may be a misplaced responsibility to begin with. But instead, I’m able to go to these conversations with genuine ambition that’s not urgent. It’s an invitation to these donors to participate to get us to another level. But I can also look the donor in the eye and honestly say, “We’re good.” It’s almost like a position of power in this donor conversation, but I’m able to get there because I have chosen to not take this ultra urgent approach, a more scientific, we’re going to roll it out as we have it kind of approach.

Eric Ressler [00:24:35]: I’m realizing that what we haven’t done is we haven’t talked about why urgency actually can work at times. So when we think about, this is reminding me of maybe timeliness or even just structure is a better word for it, but when you think about fundraising campaigns, capital campaigns, end of year campaigns, there’s an urgency built in where it’s like, “Hey, we need to raise X amount by X date.” And usually it’s somewhat arbitrary, honestly. Even end of year campaigns, what’s driving that? Taxes. But what it does is it creates an urgency on behalf of the donor to act within a certain amount of time.

You see this in social psychology and app design where it’s like, “Check out now on your concert tickets before they’re gone.” So this is not distinct to the social impact space, but even in hearing the way that you framed that urgent fundraising appeal, which I know is not your style, it felt so icky, man.

It felt guilt trippy and it felt... What I heard is this is an org that doesn’t have their shit together because if I don’t, out of the blue, make a gift, they’re in trouble. And look, there are times where the state of play creates those scenarios where all of a sudden a totally viable, sustainable, tried and trusted model of fundraising disappears overnight because USAID disappears overnight. Hey, no harm, no foul to the orgs who were affected by that. But if that’s just your standard operating model, again, it’s just like, what’s going on here in this place where everything’s urgent all the time and our fundraising, if we don’t get this one gift, the org disappears? That doesn’t seem like a solid sustainable organization.

Jonathan Hicken [00:26:35]: I think you can also unintentionally slip into this, like you said, icky space where, especially if you’re dealing with human health or human wellbeing or life and death issues, that false urgency is putting an emotional burden on your audience that just isn’t fair to do. I almost feel like it should be a sector faux pas.

Eric Ressler [00:27:00]: Yeah, it’s manipulative.

Jonathan Hicken [00:27:05]: Yeah, it’s a bit manipulative. Yeah. I know you said it tongue in cheek, but this idea of an urgency budget, I think there’s actually something to that where... Actually, I have this friend, and I’m going to get bleeped a couple of times on this right now, but I have this friend that believes that you’re born with a limited number of fucks to give, and in your 20s, you just blow your fucks away. And then you get into your 30s, you’re like, “Oh, I got to start budgeting these fucks.” And actually that has stuck with me so much where I got to budget. I got to budget the fucks I give.

Eric Ressler [00:27:40]: Yeah, it’s so real.

Jonathan Hicken [00:27:40]: It’s so real. I say that in jest, but also there’s something real about that, even as delivering urgency to your audience.

Eric Ressler [00:27:50]: Yeah. I feel like we were talking about this just the other day where even this comes down to the individual level at the end of the day for a leader. When something lands on your desk, having almost an urgency filter: is this actually urgent? Is it urgent to me or is it urgent to whoever is asking for the request? Obviously, the context matters a lot there, but I found myself being much more intentional and, I don’t know what the word would be, but just brutal even about what I agree to from an urgency standpoint.

For example, sometimes people come to us and they have a really urgent request and it matters a lot to them. And as much as we want to come through for people, what’s the old saying, “Your lack of planning is not my emergency.” And it’s really easy to get sucked into that stuff, especially in an agency relationship where there’s this professional service or service-based expectation that we must serve the client.

And I think we are in service to our clients, absolutely, but more so we’re in partnership with our clients, and that’s not a way to treat people. Now look, we also have clients that we’re deeply in partnership with who we’ve worked with for years, and they don’t abuse that, and when they come to us with an urgent request, if we can do it, we’re going to make it happen.

Jonathan Hicken [00:29:10]: Yeah, because you believe it, you’ve earned that trust.

Eric Ressler [00:29:10]: They’ve earned it. Yeah, they’ve earned it, and we’re happy to give it. And we know that if we have an urgent request, they’d do the same thing for us, right? If, let’s say, they slipped up on a payment or something and it’s late and it’s going to affect our cash flow, they’re going to do what they need to urgently to move it through the process faster than they typically would, for example. So I think that’s something that I’ve been thinking about because it’s really easy in our culture for every new request to rise to the top, it becomes urgent at the expense of things you already have planned, and then all of a sudden you’re just stuck in this urgency hamster wheel.

Jonathan Hicken [00:29:45]: I think that story of your partnerships with your clients is actually a perfect allegory for what we need to be thinking about in the space, especially as it relates to fundraising appeals, where we need to build that trust and that relationship with our donor base, whatever that looks like, and that’s first. That has to be first. And so when you do call for that urgent support, they’re going to trust that it’s real. And I think that’s at the base, the foundation of all of this: the erosion of trust with social impact work because of all of this constant and loud false urgency.

Eric Ressler [00:30:20]: Yeah, I think that’s it, man. And I would just add, it’s the same on the team side, right? If everything’s urgent all the time for your team, then that just builds in that tone. And then pretty soon people learn none of this is actually real. None of this is actually urgent. Or if it is, this is messed up. I don’t want to be here where everything’s a fire all the time.

So look, this is a balance. I’m not saying that this is easy. I think it’s something that you need to constantly calibrate and check in on. But yeah, let’s build our urgency budgets in alongside our fiscal budgets and let’s use them wisely. And let’s think about when we don’t use them wisely, who is it that actually pays? Because it’s usually our supporters or our team members and even ourselves, and it’s just not worth it.

Jonathan Hicken [00:31:05]: Yeah. Hear, hear. All right. Thanks for bringing this one up, Eric.

Eric Ressler [00:31:10]: Yeah, man, thanks for unpacking it with me. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Every cause depends on people knowing what’s happening around them: how the school board voted, what the county plans to do about its water system, who is running for sheriff and why. In a growing number of American communities, nobody is reporting any of it. Between 2002 and 2025, newspapers cut about 75% of their newsroom jobs, and two to three papers still close every week. Matthew Copeland calls this a classic market failure, and he runs a newsroom built on a different model.

Matthew is the Chief Executive and Editor of WyoFile, an independent nonprofit newsroom covering the people, places and policy of Wyoming. He started with WyoFile as a freelance writer and took over its leadership in 2017, when the organization was four people with a couple of months of payroll in the bank and a heavy dependence on a few institutional grants. WyoFile now has 16 staff, an audience more than ten times larger, and its stories were republished about 3,000 times in the past year by newspapers across the state.

The model is simple. WyoFile asks people to fund journalism as a public good, the way a community funds its food bank or volunteer fire department, and spends that money on reporting. With profit margin out of the center of the mission, the newsroom has no need to chase attention by picking sides or sensationalizing the news. Its work breaks into three jobs: give people the information they need to take part in civic life, watch over the public’s business, and get accurate facts out early enough to crowd out misinformation before it spreads.

Matthew and Eric also dig into why facts keep losing the fight for attention, and why Matthew gives his best answers in person. WyoFile editors pick up the phone for every angry reader email, and many of the newsroom’s strongest supporters started out that way. As AI reshapes search and platforms fill with bots, he expects people to place a much higher value on human connection.

For leaders working outside journalism, Matthew borrows a line from the late John Thornton, co-founder of the Texas Tribune and the American Journalism Project: whatever your first cause is, your second should be access to information. Every mission is shaped by how information reaches people and what they do with it, and both are changing fast.

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Episode Highlights:

[00:02:05] WyoFile’s mission and its three mandates
[00:04:00] Crowding out misinformation with facts
[00:06:35] The collapse of local news, by the numbers
[00:10:00] Funding journalism like the fire department
[00:11:40] From “three guys and a dog” to 16 staff
[00:13:35] 3,000 stories republished across Wyoming
[00:15:55] Why chasing attention skews the news
[00:19:35] Why trust holds up at the local level
[00:25:05] Ideas need an arena of fact to compete
[00:29:30] Facts are losing the battle for attention
[00:34:25] Make it human and take it off the platform
[00:42:45] Why your second cause should be access to information

Notable Quotes:

[00:43:15]: “No matter what your number one cause is, your number two ought to be access to information.” Matthew Copeland

[00:04:55]: “The truth does a particularly poor job of standing up for itself when there’s not very much of it around.” Matthew Copeland

[00:10:50]: “So too do we need to think about access to the facts as an essential component of a functioning society and funded as such.” Matthew Copeland

[00:26:00]: “That competition of ideas is only functional, is only productive, if it’s conducted in an arena of fact.” Matthew Copeland

[00:29:20]: “There really isn’t necessarily a shortage of facts so much as facts are losing the battle of attention.” Eric Ressler

[00:48:50]: “Get in the game, get off the comment section and turn the energy that maybe would be spent lobbing grenades into trying to make an impact with and for your community.” Matthew Copeland

Resources & Links:

• WyoFile: Matthew’s independent nonprofit newsroom covering Wyoming

• Matthew Copeland’s bio (American Journalism Project): background on Matthew and WyoFile

• Matthew Copeland LinkedIn

• Institute for Nonprofit News: network of nonprofit newsrooms, mentioned at [00:47:55]

• Find Your News (INN directory): search for a nonprofit newsroom near you

• American Journalism Project: venture philanthropy for nonprofit local news, mentioned at [00:48:15]

• The Texas Tribune: nonprofit newsroom co-founded by John Thornton, mentioned at [00:43:00]

• A tribute to John Thornton (American Journalism Project): source of the “number two cause” idea

• Timothy Snyder: historian quoted at [00:04:30]

• Wyoming Press Association: the state’s newspaper association, mentioned at [00:13:45]

• Medill State of Local News 2025: data on newspaper closures and news deserts, context for the figures at [00:07:00]

• Angus Thuermer Jr. joins WyoFile: the WyoFile reporter quoted at [00:11:55]

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:00:55]: Okay, Matthew, thank you for joining me today.

Matthew Copeland [00:00:55]: Of course. Thanks for having me, Eric.

Eric Ressler [00:01:00]: So I’m really excited to dive into a lot of topics with you here. We’ve had a couple discussions on our show about the information ecosystem, mis and disinformation. In my opinion, one of the most critical and often not really talked about enough elements of social impact work, civic engagement, and one of the biggest issues in the world right now. And a lot of orgs are working on it in different ways, but I fear that we are being outpaced by technology and culture and some of the worst impulses of human psychology and humanity. So we’re going to have a fun show talking about all that today. How’s that sound?

Matthew Copeland [00:01:40]: I share your concerns.

Eric Ressler [00:01:45]: Well, I’d love to start to just learn a little bit about, and for our listeners and viewers to learn a little bit more about, the work that you’re doing around local journalism and what drives that work and how you’re seeing this problem and how you guys are working on it, even just at the local level, and the trends that you’re seeing more nationally and internationally as well.

Matthew Copeland [00:02:05]: Yeah. In terms of what drives the work, we are genuinely a mission-driven organization here at WyoFile. That’s a phrase that is bandied about all the time. It almost feels like requisite speech. As often as not, it’s more lip service than it is fact, but we actually do turn to the mission on a daily basis as a compass for us in helping us make coverage decisions, editorial decisions, business decisions about do we zig or do we zag?

WyoFile’s mission is to inform and engage Wyoming with in-depth reporting in the public interest. To be fair, there’s a fair bit of elbow room in that. You could interpret that a number of different ways. So we’ve been very deliberate in defining what we see as three distinct mandates in that mission, or three distinct calls to action. One, first and foremost, and really top line in terms of what gets the lion’s share of our attention and resources, is that it’s our job to make sure the people of Wyoming have the information they need to participate effectively in civic life. Whatever they want that participation to look like, towards whatever ends are important to them, whatever the cause, whatever the issue, whatever the project, making sure they’re able to do that fully informed by the facts.

Second, in no way secondary, and in fact, if you ask most people at WyoFile why they came to work here, this is a big part of it. And that’s to be the watchdogs. It’s our job to make sure the people’s business is being conducted out in the open and in the sunlight where everyone can see it. And when it’s not, to drag it kicking and screaming if necessary out into the open where everyone has the benefit of that information.

And then third, and this is unfortunately increasingly taking up a good deal more of our emphasis out of necessity, and this touches on what you mentioned there in the intro about your concerns about being outpaced, is it’s our job to set the record straight initially as opposed to try and correct it after the fact. But put another way, it’s to crowd out misinformation, disinformation, propaganda and lies with the facts, to provide that alternative to what we are increasingly seeing driving our political and civic discourse in this country.

Timothy Snyder, formerly at Yale, history professor, I believe he’s in McGill now in Canada, widely regarded as one of the world’s leading experts on tyranny. I think he said it very succinctly in that the truth does a particularly poor job of standing up for itself when there’s not very much of it around. When we think about that third call to action, you can think of it in terms of making sure there’s plenty of it around, because unfortunately the trend is pointing the other direction. With all of the information that we have out there today, with all of the voices, all of the ever-dividing channels and ways to acquire information or to use the term of the day, content, there is actually a decreasing volume of valid factual information about what’s happening at the local level, the information people need to participate and to engage.

Eric Ressler [00:05:50]: Yeah, and I think let’s go there a little bit specifically about the local level, because my sense is that even in my early childhood, but certainly before that, there was a little bit more of a shared sense of truth and reality, broadly speaking. Of course, there’s always edge cases, there’s always going to be tinfoil hat type individuals who have their own idea about what’s real. And there were basically a few public broadcast stations on TV. You read your local newspaper, there were maybe one or two of them. They were actually well-staffed and actual real journalists worked there and there was a viable business model there. And my sense is that entire paradigm has completely collapsed for the most part. And I think...

Matthew Copeland [00:06:35]: It’s completely shifted, and I think it’s fair in many sectors to describe it as a collapse. And to be clear, it’s a collapse driven by really a classic market failure. The models that sustained the institutions that we have relied on for generations are not working the way that they have for generations. To quantify that for you a little bit, give some numbers to that, between 2002 and 2025, American newspapers shed about 75% of their newsroom jobs.

Eric Ressler [00:07:15]: Wow.

Matthew Copeland [00:07:15]: We’re just talking about newsroom jobs. These aren’t people running the presses. These aren’t people delivering papers or selling ad space. These are journalists, reporters, editors, photographers, et cetera. We’re talking about 80,000 folks, upwards of 80,000 folks that are no longer out there digging, no longer out there revealing, no longer out there reflecting the community to itself, no longer out there facilitating the essential conversations that we need to be having as neighbors and as towns and as counties about how we’re going to pave Main Street and what we want the sheriff to be focused on and who we should send to Washington DC and who we should send to prison.

If you look at an institutional level, today somewhere between two and three American newspapers shutter every week on average, primarily local institutions. 37% of those American papers have already folded in the last 20 years and they’re not coming back. And as you described so clearly, far more of them, the vast majority in many cases of those that remain, have become shells of their former selves. In some cases, literally empty mastheads or ghost papers that are no longer able to effectively cover their communities.

And I want to be careful here and be clear that I’m not trying to be disparaging of these institutions in any way. These are hardworking folks who certainly aren’t in it for the money, they’re not in it for the glory. In many cases, they’re going around every day doing their job with a target on their back and getting beat up for it, and they’re doing the essential work, but the model has collapsed to the degree that they do not have the resources they need to be able to continue doing that in an effective way. We need to find a better way forward, and that’s really an essential component of why WyoFile does what it does. It’s not just the providing this essential public service of informing the public, but doing it in a way that builds a movement, doing it in a way that demonstrates a new path forward so that we can know we will have sustainable, reliable, ready, universal access to the facts going forward.

Eric Ressler [00:09:45]: Can you give us a little bit more detail around how you’ve built something that works in the current environment, in the current market, in a way that the traditional local paper doesn’t?

Matthew Copeland [00:10:00]: Yeah. So I think it starts with putting access to the facts, public interest journalism, at the center of the mission as opposed to profit margin at the center of the mission. And that enables you to do a lot of different things differently. We approach journalism first and foremost as an essential public good, and we ask people to fund it as such, in the same category of: it’s essential as a community to fund the local food bank to make sure that the neediest among us aren’t going hungry, and the volunteer fire department to put out the flames, and the Red Cross to help our communities recover from disasters when, God forbid, they strike. So too do we need to think about access to the facts as an essential component of a functioning society and funded as such.

So at the risk of oversimplifying, our business model is at the end of the day pretty simple. People give us money and we spend it on producing top-notch journalism. There’s obviously a little bit more complexity to that and how we pursue it, but at the end of the day, that’s what it boils down to. And the good news is it’s working. In the face of this environment where we’re seeing such rapid and accelerating declines in capacity in other sectors, we and colleague organizations like ours around the country have been able to add new capacities and bring new resources to bear.

To put that in scale or in context, I had been involved with WyoFile for a number of years, but I assumed this role as the leader of the organization in 2017. And at that point, we were, in the words of one of our longstanding reporters and a Wyoming journalism legend, a guy named Angus Thuermer, “three guys and a dog.” He was diplomatic enough to not name the dog. I think we all understood it to be me, but we were a four-person shop and like so many news organizations, it was nip and tuck. We had a couple of months of payroll in the bank. We were existentially dependent on a couple of big institutional grants. And frankly, we weren’t quite sure how we were going to keep the lights on. We were forever flirting with insolvency.

And today, by contrast, we’ve quadrupled in size. We’re 16 staffers strong. We have, without a close second, the most experienced, most accomplished, most professional newsroom in the state. Our audience has multiplied by more than a factor of 10. And I think this is an important point. Not only has our direct audience exploded, the folks that are finding their information on wyofile.com or via our social channels or our podcasts, et cetera, but we’re also filling the state’s newspapers and other news outlets with high quality coverage for free. That’s baked into the mission cake. There’s nothing in that mission to inform and engage Wyoming with in-depth reporting in the public interest that says anything about on wyofile.com. It’s our job to make sure that people have the information wherever they choose to find it.

Eric Ressler [00:13:45]: So your stories are distributed in other papers in the state?

Matthew Copeland [00:13:50]: Yeah. So to give you an idea, I believe there’s 39 extant members of the Wyoming Press Association, which is the newspaper association here in the state. Most of those are weeklies, so call it 52 editions a year, give or take. Collectively, that community republished WyoFile stories about 3,000 times in the last 12 months.

Eric Ressler [00:14:15]: Wow.

Matthew Copeland [00:14:15]: Yeah. We are working closely with those partners to make sure that at the local level, those communities have a nutritious information diet available to them.

Eric Ressler [00:14:25]: My sense is that this is a pretty special scenario, in the sense that many communities at the local level have either a shell paper that’s private equity backed and stripped of its true mission and value, or nothing, or something more at the state level. And so there’s a lack of proper journalism happening at the local level.

And then I also want to talk about the international and national level of journalism that’s happening too, because my sense in observing that is that even some of the biggest and most acclaimed papers and television stations... The media is clearly very bifurcated at this point between all different forms of media and short form and social, et cetera. My sense is that there’s been a pretty distinct move towards opinion-based journalism and what I would describe as sensationalized journalism, even at some of the biggest papers. And if you look at the same story, even just to make it a little bit more blunt, in AP News versus the New York Times reporting on the same issue, the flavor of that reporting, the emotion of that reporting, is going to have a very different register. Is that something you agree with? Do you observe that too? Am I getting that right or wrong? What’s your take on that?

Matthew Copeland [00:16:00]: Absolutely. Insofar as paying the bills is dependent upon driving audience numbers, and I don’t want to diminish the importance of audience, right?

Eric Ressler [00:16:10]: Yeah, of course.

Matthew Copeland [00:16:10]: The best journalism in the world is not going to do anybody any good if nobody reads it, nobody engages with it, nobody trusts it, nobody uses it in their daily life. But insofar as you’ve got a model that is built around keeping the lights on by acquiring and holding on to people’s attention at all costs, the incentives get pretty skewed pretty quickly. Really, the most reliable, the fastest, the easiest, probably the cheapest way to acquire regular engagement is to pick sides. It is to preach to the choir, to find your choir and hold onto them, and to be sensational, to grab attention. A lot of what needs to happen to make our society work is not sensational. It’s pretty boring.

Eric Ressler [00:17:15]: Pretty cut and dry. Yep.

Matthew Copeland [00:17:15]: When we talk about paving Main Street, we talk about upgrading the water infrastructure in our community. It’s also not simple stuff. It is stuff that is complex. It has nuance. To really understand it, you need to understand the context, you need to understand the history, you need to understand the stakeholders and their perspectives. And it’s a different approach. I’ve been enormously gratified over the last, call it a decade, in seeing the degree to which people do find value in that and do choose to give their attention to that when it’s something that’s made available to them, when it’s something that they understand, when it’s something that they understand where it’s coming from, which is to say they have a relationship with the institution that is producing this information. They have relationships with the people and understand that it’s a human enterprise and know these people as their neighbors.

Eric Ressler [00:18:20]: Well, let’s get into that, because what I’m concerned by, and I’m not the only one concerned by this, is that there’s been a growing trend to basically have distrust in institutions, distrust in media, specifically “mainstream media.” And I’m not even saying that we should not have a healthy amount of skepticism from any publisher. I think having a generally skeptical viewpoint around any piece of information is a basic life skill at this point, just given how much misinformation there is. And even the biggest and best journalists get it wrong sometimes. They just do. And it’s not even for nefarious reasons, it usually isn’t. It’s usually just a mistake. And the difference is that actual journalists then publish a retraction instead of just moving on to the next viral post.

Nonetheless, there seems to be in our culture more grace given to individual personalities and influencers getting things wrong, even when they have horrible incentives, a clear political agenda. When they make mistakes, it’s whatever, but anytime mainstream media makes even the smallest mistake, it’s just more proof that you can’t trust the mainstream media. What’s going on there?

Matthew Copeland [00:19:35]: I think one of the things that’s going on there is the fact that we are talking about national and international things by and large that are far from home and that people don’t really have an opportunity to have as much of a meaningful impact on. They do not see the direct correlation with what’s happening in their daily lives. And I think that is part of why, with those plummeting trust numbers, the one place we see a lot more strength in faith in the “media” is at the local level.

Eric Ressler [00:20:10]: At the local level, yeah.

Matthew Copeland [00:20:10]: The problem is that there’s so much less of it at the local level. And I think that’s problematic for our discourse in a lot of ways. The founders built our nation with a great deal of local control for a reason. There’s a lot of philosophy and thinking behind this, in that communities work together to accomplish the things that they can together, to address challenges, to capitalize on opportunities, to chart their own course, to define what prosperity looks like and means for them collectively. But obviously smaller groups have limitations, and so the local system feeds into a state system that can fill in the gaps between what communities can do independently. And ideally, a robust and engaged state system then rolls up to and informs a responsive federal system that is reacting to or responding to what the states need. I think we all remember high school civics class.

The problem though, and what we’re seeing way too much of today, is when the foundation of that type of local participation and engagement erodes, and a huge part of that is access to information about what’s going on. When that erodes, the power flow inverts. And instead of talking about how do we want to grow and nurture and diversify our local economy, we’re talking about distant, opaque, considerably less responsive institutions. The conversations become simpler. We’ve all seen this: the soundbite-centric public discourse, the zero-sum, with-us-or-against-us politics, the oversimplification of the very real and very complex challenges that we need to address together.

Eric Ressler [00:22:30]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

And I think my fear is that some of the ugliness and messiness at the national and international level seems to be trickling down to the local level, some of the tactics at least, especially when we get into politics. But the other thing I think that’s harder and harder to separate, unfortunately, is fact from politics, because politics in the best cases are built on facts. That doesn’t seem to be happening quite as much these days, but even the concept of what’s true and what’s real is becoming politically motivated in a political battle where we can’t even agree on basic principles of science in some situations, right? And so I’m watching local issues being debated in the same way that international issues are being debated now, where instead of this community constructive disagreement, let’s-figure-out-solutions oriented mindset, it’s just this polarized, tribal, black and white lack of nuanced thinking.

And my frank sense of it is that 90% of that blame goes to the medium of the internet, and that if those same conversations were happening more exclusively, or exclusively, in rooms, and the internet were not in the room or part of that forming of beliefs and ideas, we would be talking to each other much more like we’re having a conversation right now. We might disagree on some things and we can talk about why and get curious and interested about that. And I just fear that the trajectory doesn’t seem to be going the right way for us as a society with regards to those basic common agreeable truths. Do you see a counter story there in your local work? How do you think about the distinction there?

Matthew Copeland [00:25:15]: I do see a counter story there. In fact, the counter story is a large part of why I do this work. For me, it comes down to the competition of ideas. We don’t agree. There’s an infinite number of things that we don’t agree on and never will agree on, and that’s perfectly fine. Frankly, I think that’s part of the American secret sauce. I think that’s a huge driver of what has made us such an incredible nation for 250 years now. Let the best idea win. It is the purest and I think most important and most impactful application of the free market principle. The problem is that competition of ideas is only functional, is only productive if it’s conducted in an arena of fact, and that’s increasingly not the case.

What we often tell folks is, look, it’s not our job at WyoFile to tell people what to think. It’s not our job to tell people how to think. It is our job to make sure that thinking at least has the opportunity to be informed by the facts. To choose a very silly example, I’m talking to you from Lander, Wyoming, where 30 below is something that we experience most winters. There, I think, is a valid debate to be had about what the best way is for us to efficiently and effectively heat our homes and structures in Wyoming. We constantly need to be improving on that front, and I think we can have a productive debate about that. We can’t have a productive conversation about that though if one part of that conversation is coming from a perspective of, well, it just doesn’t get cold here. That’s just factually untrue.

And it’s a really silly example, but I’m afraid that frankly, it’s not that far-fetched when you look at some of the conversations we’re having at the national level, and unfortunately at the local level too, because so many of those essential local conversations are being supplanted by what I think could fairly be described as a brand loyalty debate. Are you red or are you blue? The ideas don’t matter. It’s whose team are you on that I care about.

Eric Ressler [00:27:45]: Yeah. And I think that’s the part that I am, I guess, somewhat skeptical of. What I’m hearing you say is that the free marketplace of ideas is the solution there, and that facts are a big part of that. And if more people just had access to the facts, this would solve itself. I’m very much oversimplifying your argument, I think, but let’s just go with that as a thread here. And my concern is that facts are, I think you even had a quote early in this episode, that the truth is something that there’s not enough of and doesn’t stand on its own. And I think what I’m seeing and what I’m concerned by is that team-based, tribal, sensationalized, emotionally driven dis and misinformation, if not propaganda, seems to work better on our psychology and be more effective, especially for just the average citizen who maybe doesn’t really care about civic engagement or politics as much and is just trying to get by, which, no shade there whatsoever. They’re going to fall into that trap a lot easier than the, “Well, let me get three perspectives and look at the primary sources.”

And so journalism traditionally did a lot of that legwork for society, and I think that’s maybe what you’re saying a little bit more of, because I don’t think just putting the facts out there... The facts are out there, right? There’s more access to facts than ever before, maybe not quite at the local level, but because of the sheer amount of access to information most of us have now, there really isn’t necessarily a shortage of facts so much as facts are losing the battle of attention. Agree or disagree?

Matthew Copeland [00:29:30]: Yeah, no, I agree that facts are losing the battle of attention for sure. In part, that is driven by a dearth both of the facts at the local level, but also of people’s relationship to them and with them. I described earlier building and demonstrating a new model, building a movement. That’s a big part of this movement. It’s, again, not just the providing of the facts, but giving people an opportunity to put skin in that game, giving people an opportunity to recognize how essential that access is and what we lose when it goes away, and to not only invest in it with their pocketbooks, but to do it with their time and their attention and in their conversations and with their neighbors and in their community.

There has never been more competition for our attention than there is right now. That’s accelerating. That’s very much accelerating. And frankly, the technology and its practitioners are very good at that. We’ve got more than a century of advanced psychology that lays out pretty well for us how humans respond to various stimuli. And we have built tools that we carry around in our pockets that are very, very good at pushing those buttons for us. And that is a problem. I am not so Pollyannaish as to believe that providing the facts solves all our problems.

Eric Ressler [00:31:30]: Sure.

Matthew Copeland [00:31:30]: We’ve got a lot of challenges. We’ve got a lot of puzzles that we need to figure out. We’ve got a lot of opportunities that we need to figure out how to capitalize on. And simply flooding the zone, as it were, with valid, valuable, factual information is not going to get the job done on that. I do know that we can’t do the job without it though. It is a necessary precursor. Whatever it is we’re trying to solve, whatever it is we’re trying to address, whatever it is we’re trying to accomplish, we can’t do it unless we have folks engaged with the information that they need to do so.

Eric Ressler [00:32:15]: And I think that’s especially where the local comes in. If there is a new growing shortage of facts, it’s at the local level compared to the national and international level, because of this degradation and collapse of the local media environment that’s happened over the last couple decades. And I definitely don’t mean to diminish the importance of journalism and facts and truth and putting that into the limelight. And I think you’re aligned here that that’s not going to do it on its own, yet we also can’t do it without that part. That’s a prerequisite to the rest of it.

But even just thinking about, and frankly watching, maybe not so much colleagues, but definitely friends and family fall, and myself even, frankly. I think all of us are not immune to this. Having beliefs reinforced and having algorithmic tuning gets you into rabbit holes where you see one YouTube short about a thing and then all of a sudden three weeks later you’re down into some weird fringe category. Like, how did I end up here? And especially when the incentive of those platforms is attention at basically all costs, and we know that humans have to a degree a bias towards things that trigger their emotions, especially negative emotions. You talked about these psychological tunings. The platforms are well aware, we’re seeing this play out in real time in the courts right now, that they are willing to trade public harm for profit and for attention, because attention is their currency of profit.

And so part of me is like, do we need almost some kind of movement-based revolution? Is it regulation on these platforms that needs to happen? How do you compete in this marketplace of ideas in the current state of play with technology without falling prey to some of those same traps that the big tech companies have fallen prey to?

Matthew Copeland [00:34:15]: Yeah. You make it human. You literally, but I think more to the point figuratively, take it off the platform. Form direct, trusting, give-and-take, 360-degree relationships with your audience, with the communities that you are seeking to serve, and be clear and be transparent about what it is that you’re trying to accomplish and how people can help do that. Give people an opportunity to engage.

I’ve got a neighbor, we come from different perspectives politically. I think my wife put it perfectly: “Man, I love that guy so long as you don’t look at his bumper stickers.” If we were talking about national politics in a chat room, it’s not even a thing anymore, on a social media platform somewhere, I bet you it would get pretty heated pretty quickly. But when we stand on opposite sides of the fence, or we’re both out grilling burgers of a Wednesday evening and are chatting about what’s going on locally, that’s something that we have in common. It’s something that we can talk about with nuance and with perspective. And again, we’re not necessarily going to agree on that, but it can be a productive disagreement.

We need to be doing that at scale within the communities that we seek to serve. And that’s an essential part of our approach: getting out into the community face-to-face, responding to every correspondence. Many of WyoFile’s biggest champions, the relationship started with a comment on a story or a nastygram sent via email saying, “Oh, you biased so-and-so’s. Why didn’t you include this and that in the story? And I’m never going to read you again.” And one of our editors picking up the phone, like we do in every single one of those interactions, and saying, “Hey, thanks for reading. Thanks, Mark, for reaching out. I want to have a better understanding of what your concerns are. Do you have five minutes to walk me through this?” And if this warrants an addition or an update or a correction or what have you, that card is very much in the deck, that’s on the table, but I want to understand where you are coming from.

We have a little bit of a luxury in Wyoming in that we are the least populous state in the union. As I believe it was former Governor Mike Sullivan who coined the now famous phrase, Wyoming is really just one big small town with really long streets. This is a community where someone running for statewide office, governor, senator, secretary of state, what have you, there is still an expectation that as a voter, you’re going to get a chance to shake that person’s hand and look them in the eye maybe a couple of times before election day, and that you can access them after they’re in office as well. It does still have that small town community vibe to it.

We also have in our history, much more recently than I think so much of the country, a proud tradition that was maintained and executed until quite recently of explicit civility in our discourse, including with those that we disagree with. Very much a live-and-let-live brand of conservatism. People often talk about how you can’t afford to alienate people in Wyoming, because next time you end up in the ditch in February, which happens to all of us, you don’t know who the next truck’s going to be along.

Eric Ressler [00:38:30]: And there won’t be that many of them.

Matthew Copeland [00:38:35]: Yeah, exactly. And it may be a while. You’re not going to have a selection to choose from. We can still tap into that. There has been a shift like there has been everywhere nationally. It has grown more polarized. It has grown more nasty. The level of vitriol has definitely ramped up, but that is still fresh in people’s memory and it’s still something that people value, and it’s incumbent on us to find ways to tap into that and to leverage that for everyone’s benefit.

There’s an irony to that. We are a digital-first publication. We publish online at wyofile.com. Most of our reach is on digital. A lot of our engagement, a lot of our important engagement, is on the social media platforms. But using that as a pathway to genuine relationships, relationships that aren’t dependent upon or moderated by intermediaries like the social platforms, like the search algorithms, et cetera, where folks have direct access to us and vice versa, is something that really every news organization needs to be focused on right now, particularly as the way information moves around the internet is changing so rapidly. What AI has done to search almost overnight: organizations that were dependent on SEO for their audience are in a world of hurt right now. I don’t see that getting better. It really has to come down to people to people and communities together.

Eric Ressler [00:40:15]: Yeah, I think that’s dead on. And looking at this for a second through the lens of some of our listeners, who are also very mission driven, social impact focused, but probably not running a newsroom, there’s a version of this that they need to be paying attention to as well. And I think everyone is to a degree realizing the importance of digital engagement and dialogue and how that’s happening, and tuned into the social media platforms, tuned into the pros and cons of those things, because there are pros to them also in terms of building movements and missions. And also, I think, not even just worried about, but curious about how AI is coming in and shaking all of this up, even around discoverability of your mission for support that you need, whether that’s money or people power or whatever it is.

And now there’s a new intermediary that is just a new complex player in this already complex web of information cycles and ecosystems, where you might search AI for something to get truth about who I should vote for or how I should feel about this issue. AI is now pulling from social media on your behalf or other publications on your behalf, trying to figure out how and what to prioritize and to surface, which is also shaped by past conversations you’ve had with AI. So it’s just getting more and more complex. So there’s this weird moment I think that we’re in, where in-person, human-to-human conversation is going to become a premium almost at some level for our time and attention. And yet so much of what influences our beliefs and our understanding of the world around us is happening and building human context before those conversations happen, which just creates this weird... Sometimes I have conversations with friends where I’m like, “Where did you even hear that? What does your algorithm look like, man? This is the first time I’ve heard it. What am I missing even?”

So it’s a really interesting challenge. So I guess as we work to wrap up here, I want to just ask, what should other social impact leaders in the space be taking away from this, be thinking about, other than support local journalism and the importance of that? How should leaders be navigating this moment in the information ecosystem?

Matthew Copeland [00:42:45]: Yeah, I think putting a social impact leader’s particular cause in the context of an information ecosystem in the first place is a big step forward. The late, great John Thornton, one of the founders of the Texas Tribune, one of the founders of the American Journalism Project, and a very generous philanthropist, said it really well when he said that no matter what your number one cause is, your number two ought to be access to information. Recognizing the degree to which whatever it is you’re trying to accomplish is going to be affected by the availability of information, how that information travels, how people interact with that information, and recognizing that that is such a rapidly changing set of variables right now and that that has enormous impact on whatever your cause is, whatever it is that you’re trying to accomplish, is essential.

I liked a phrase you used just a moment ago about human-to-human relationships being at a premium. This is entirely anecdotal, this is entirely out of my head. I have zero data to back this up, but I think there is going to be a coming renaissance in which people start to recognize that premium and value it as such. And I think in large part it will be a direct response to people’s frustration with the alternative, people’s disgust with the alternative, and people recognizing how much better the human-to-human interactions are all around. As cyberspace increasingly becomes the purview of the bots and the technology, and less of a place that is responsive to our needs and our desires, I think folks are going to find opportunities to do meaningful work at scale offline. Not entirely. AI is not going away, social media is not going away, but thinking about those as supplements as opposed to central, I think, is going to be a welcome shift, and something that I’m always looking for opportunities in.

Eric Ressler [00:45:35]: Yeah, I also anecdotally agree, and I don’t have a ton of data to back that up either, but just observing the world, I have a sense that a lot of people are knowingly, and with a true felt sense, pretty unhappy with the current state of digital experience, and yet we can’t seem to put the phones down. And there’s even movements around putting the phones down and digital detox and all these things, but they are so well designed to hack our psychology and our attention and to basically prevent us from ever becoming bored, which is a huge issue actually for our brains. We need to be bored, because that’s where we process a lot. It’s where our imaginative thinking happens. And so I think we’re starting to see a lot of people at least having more discussions around this, and hopefully this one can be part of that.

And I agree, I’m not suggesting we go into some sort of digital fast or detox permanently, because I just don’t think that’s practical anymore, but I do think we need to majorly rethink how these technologies fit into our lives and not just basically accept whatever the big tech companies tell us we should do there, because their incentives are not aligned at all with ours, broadly speaking. But to me that actually ends on a slightly optimistic note, in the sense that if we do start to recognize that culturally, and we can reclaim the best parts of traditional media and the best parts of what these technologies do offer us as benefits, I think that is going to be a better world than either of the alternatives that we’ve talked about.

Matthew, before we do wrap, I want to just give you a chance to shout out or plug anything to our listeners who are interested in learning more about you or WyoFile or just getting engaged in local journalism. What should people dig into if they’re passionate about this and want to go deeper?

Matthew Copeland [00:47:35]: Yeah, I would encourage folks to find their independent nonprofit public interest news agency. This model is proliferating quite rapidly around the nation, takes a lot of different forms in a lot of different places, but there are innumerable organizations doing really essential work. Find it, start reading, subscribe to the newsletter. If you find value there, donate to it. Some resources on that front: inn.org, the Institute for Nonprofit News. I believe they’ve got a geographic search that you can use. They certainly have a listing of many hundreds of members. An outstanding organization that we’ve been involved with from the outset is the American Journalism Project. Their portfolio of nonprofit news agencies are really the top performers in this space, and you can find them all over the country.

I’d encourage folks to get involved with whatever that means for you, whether it’s changing the hours of the rec center so that they better serve the community, or paying closer attention to the school board, or better yet running for public office locally. Get in the game, get off the comment section and turn the energy that maybe would be spent lobbing grenades into trying to make an impact with and for your community.

Eric Ressler [00:49:10]: Awesome. Thank you, Matthew. This has been great. Appreciate your time today.

Matthew Copeland [00:49:10]: I really appreciate it, Eric.

Eric Ressler [00:49:15]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Executive directors aren’t allowed to lose steam. At least that’s the expectation in our sector. A middle manager at a bank can admit their job isn’t doing it for them right now. The leader of a mission-driven org is supposed to be all in, all the time.

Jonathan is five years into leading the Seymour Center, fresh off a major milestone, and his motivation has stalled. He can see it in how he shows up to the office, and in the energy of his team.

I know that feeling well. Early on, every dip came with shame. The organization was doing well and I loved the work, so what was my excuse?

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What changed things for me was separating burnout from a motivation slump. Burnout happens when you’ve been pummeled for too long without time to recover, and the fix is deep rest. A slump can hit when you have all the time and energy you need and still can’t find the spark.

Success makes the slump more likely. When there’s no pain pushing you, coasting starts to feel reasonable. I’ve done it, and it came back to bite me.

What gets me out of a slump is almost always new inspiration: a new idea, new peers, a new way of looking at an old problem.

So before you prescribe yourself a fix, ask which one you’re dealing with. Are you out of capacity, or out of things that excite you?

Episode Highlights:

[00:01:35] The success hangover after a major milestone
[00:02:10] Why motivation runs in cycles
[00:04:40] A leader’s mood sets the team’s temperature
[00:06:35] The expectation that executive directors are always motivated
[00:08:00] Self-determination theory: autonomy, competence, and relatedness
[00:11:00] Breaking the shame cycle around demotivation
[00:13:00] Why rest and rote tasks only go so far
[00:14:45] Pain as a motivator, and what happens when it’s gone
[00:17:00] Seeking inspiration to break the rut
[00:18:15] Burnout vs. lost motivation
[00:19:40] When the slump is really disillusionment or jadedness
[00:21:35] Work, personal life, and the guilt of stepping away

Notable Quotes:

[00:04:15]: “I notice that how I’m showing up to the office is a little more muted, but what I notice is that also the energy of the team is down.” Jonathan Hicken

[00:06:40]: “There’s an expectation that the leader, especially of a social impact organization, should always and must always be fully motivated and committed to the cause. And I just don’t think that’s a realistic expectation because we’re all human here.” Eric Ressler

[00:14:40]: “It’s almost like the fear of stagnating might be the thing that breaks me out.” Jonathan Hicken

[00:18:20]: “I think the antidote to burnout is true deep rest, and I don’t think true deep rest is going to solve your motivation issue.” Eric Ressler

[00:20:40]: “I still very much believe in the work. And so one of the big problems is I don’t even know where this is coming from.” Jonathan Hicken

[00:23:05]: “Work is important. I believe in work, but also work is not the full story, even if you’re doing important purposeful work. And I will die on that hill.” Eric Ressler

Resources & Links:

• The research behind the autonomy, competence, and relatedness model Eric references

• Designing Tomorrow episode on motivating your team: mentioned at [00:01:20]

• Designing Tomorrow episode on not coasting on your momentum: mentioned at [00:14:45]

• Designing Tomorrow episode on building culture at work: mentioned at [00:22:30]

• AAM Museum Leadership Academy: Museum-focused leadership cohort/academy Jonathan joined: mentioned at [00:17:00] and [00:19:10]

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:45]: Eric, I want to talk to you today about leader motivation, self-motivation. I find myself in a unique situation where I find my motivation is waning and I can’t be the only executive director of a social impact organization who feels this. And so I wanted to spend a little time with you today to unpack what that means for leaders, what that means for organizations, and ultimately, self-servingly, how to break out of this little rut that I’m in right now.

Eric Ressler [00:01:20]: Yeah, I love this. I’ve thought deeply about this and done a little research too in the past. I know we did an episode, I think, about how to motivate your team at one point. Now we’re flipping it around. How do we stay motivated as leaders in this space? I love it. Let’s go.

Jonathan Hicken [00:01:30]: So I’ve been in the role five years and we just hit some major milestones and it was a huge success. And I find myself in the few weeks and months following that big milestone moment in a bit of a lull. There’s this maybe coming down, it’s almost like a success hangover or something where I’m trying to figure out how to get back in touch with that motivation. And I’ve tried a few things and so far it has been mildly successful, but I know there’s still a way to go. You’ve been at your role for 16 years.

Eric Ressler [00:02:10]: That’s right.

Jonathan Hicken [00:02:10]: Have you experienced this before?

Eric Ressler [00:02:15]: All the time, man. Yeah. I feel like my motivation and inspiration is very cyclical. It is not steady. And there are times where I feel like I’m just having to do the work and I know that it’s important and I have methods and beliefs around how to get that done and structures to a degree. But my inclination and my excitement comes from new things, new ideas, new ventures, new partnerships. I think that’s actually one of the reasons why running an agency is overall a really good fit for me, because I get a lot of new learnings, new opportunities, new people I work with all the time. On the flip side, I can struggle sometimes with the follow-through. I love the new idea phase, I love designing the idea, but then actually seeing the idea all the way through can be hard for me.

Maybe it’s a patience thing, maybe it’s, I don’t know, it’s just not as exciting for whatever reason for my personality. So I struggle with this and there are times that I feel excited, inspired, motivated, jazzed, use your word, and then times where I’m just showing up and going through the motions. And I sometimes question, is this constructive? Might this be a time to actually pull back a little bit and take a little time off, or do I need that? This also brings to mind, do you feel like there’s a difference between a loss of motivation and burnout? I think there is, but I’d be curious to hear your take on that.

Jonathan Hicken [00:03:50]: It might be. It might be. I don’t think that that is necessarily the acute reason for my particular state, but the thing that’s bringing it to my attention is I’m noticing the impacts of my lack of motivation, and bringing this back to how do we create excellent social impact organizations when in this particular situation you have a leader who’s lost their motivation a little bit. And so the things that I’m noticing is I notice that how I’m showing up to the office is a little more muted. I’m usually a very... Yeah, preferious. Yeah. And I haven’t been, not to say that I’m a Debbie Downer, but what I notice is that my team, also the energy of the team is down.

Eric Ressler [00:04:40]: Yeah. I’ve noticed this many, many times over the years, mostly in reflection of when I’ve not shown up as my best, when I’ve been stressed or demotivated or even at points definitely burned out. And it’s hard to put a mask on. And I actually don’t even know that you should be putting a mask on around that. But what I have noticed is that, unfortunately, my mood, my vibe, my essence, whatever, has an outsized impact on my team. And I wish it weren’t that way actually. And I’m not saying that everything that happens on my team is because of me so much as that I think your team looks up to the leader as a signal, as a temperature check on how they should be acting and showing up. And at times certainly, and I’m so thankful for my team, even when I’ve been in those states, there are other team members who have shown up and cracked a joke that just got me out of my shell or whatever it is.

So it definitely goes both ways, but it’s something that I’ve learned over the years that I didn’t expect, honestly, in starting an organization. I didn’t realize how much influence my mood and my vibe really have on how the team shows up, how the clients react, all of those things. So it’s something I’m acutely aware of.

Jonathan Hicken [00:05:55]: The other thing that I’m worried about is that I’ve got a couple of really important fundraising moments coming up. And one of my most important roles here is to get our supporters jazzed about what we’re doing. And so there’s this anxiety a little bit about how am I going to show up when I need to be really pitching this enthusiastically? And I think I have it in me to put it on for that day that I need to. And I’m confident I can get there, but there is that worry about, oh, is this lack of motivation going to trickle down and impact the organization in these other ways?

Eric Ressler [00:06:30]: Yeah, I think that’s a real fear. What I would say, especially to our listeners, but to you also, is I think there’s a permission thing here. I think there’s an expectation that the leader, especially of a social impact organization, should always and must always be fully motivated and committed to the cause. And I just don’t think that’s a realistic expectation because we’re all human here and leadership can be difficult at times. And to expect to be consistently at the top, motivated at all times, I think is just not, A, a realistic expectation. But I do think, B, there is a different set of criteria around it. It’s a little bit more acceptable to be demotivated as an individual team member, I think sometimes, and/or working not at a social impact organization. If you’re a middle manager at a bank, it’s socially acceptable to be like, “I’m not very motivated by my job right now.” But when you’re the executive director of a dynamic, important social impact organization, there’s this expectation that motivation should and must always be high.

But I think that’s at odds with our psychology at some level.

Jonathan Hicken [00:07:50]: So I have two questions then. One is, what are some of your strategies for overcoming this? And two, how do you find the motivation in those moments where you need it?

Eric Ressler [00:08:00]: Okay. Before I answer that, I actually want to... I remember in doing some research on team motivation, something about just basic psychology that I remember learning even in early college years. And it’s this concept of self-determination theory. Have you heard about this? No. So some scientists, I can’t remember their names, but we’ll link to them in the show notes, studied this deeply. What actually motivates people? And I think they did some studies specifically about work and they concluded that it came down to these three things, which I’ve been paying attention to both for myself and for my team. So the first is autonomy, which basically means I feel like I can do the things that I want or need to do and I have some autonomy or agency in making those choices. So that’s one. The second is competency, which is I feel like I’m good at what I do.

I’m competent in my job. And the third is relatedness, basically meaning I’m around people that I can relate to and I feel good working with. And when you think about our work in the social impact space as leaders, it seems like we should pretty easily be able to check all of those boxes. And I feel like overall I do, although what I will say is often when I feel demotivated, I’ve found it’s when I don’t feel like I have autonomy, which sounds weird because I’m the owner and I can do what I want at some level, but also I have commitments that I’ve made and I have things that I know must be done that I’ve signed up and committed to do that maybe I don’t particularly enjoy. There are parts of the work that I find tiresome or tedious and I will procrastinate on those things even though I know that they must be done and they’re important to do.

And in the current state, they’re not something I can delegate. They’re not something I can hire out and I’ve signed up for that. It’s a commitment that I’ve made. I’ve thought about this more so through the lens of team members. And I think when team members, individual contributors, feel like they don’t have autonomy, that’s the one that I think is the most impactful. And I think when people do feel like they have autonomy, they can really come out as their best selves. And obviously they’re all really important. If you don’t feel competent... And this is one actually I think that maybe leaders, and frankly I feel sometimes as you grow into leadership, you’re going to find yourself in situations where you’re doing stuff for the first time. You probably aren’t going to feel very competent. This ties into this sense of imposter syndrome when you’re spinning up a new thing or you’re learning something as an individual, as an org.

So all of these I think have a place in our work that we should be considering. And even relatedness, I think it would be worth digging into because at times, again, there’s this thought of, well, of course we’re doing good work and we’re passionate, so we must relate to one another. But the human condition is much more complex than that. Just because we’re aligned on a mission doesn’t mean we’re necessarily going to relate to one another from an interpersonal stance, and there may just be some conflict there too. So I just want to ground the conversation in those things because I feel like it’s a helpful mental model more than anything.

In terms of what I do when I feel demotivated, I think as I’ve been doing this longer, I’ve learned that it’s temporary, because early on when I felt demotivated, it was often paired with this sense of shame. Why am I demotivated? Objectively, I have it really good. We’re successful as an organization. We’re doing good things for good people. I’m doing work that I love, that I believe in. How can I possibly lose my motivation? So it came in this cycle of shame that would happen. So one thing I’ve definitely gotten a lot better at is acknowledging, hey, this is just part of the process. What I haven’t done successfully that I’d love to riff with you on is how do you not just acknowledge that, but act on it in a way that is constructive and not tipping into laziness, right? Because there are times where I’m just like, I want to play my piano. I feel motivated to do that right now. And then there are also times where I’m just like, I’d put the piano away for something that I want to do for the business.

So I don’t know, hopefully that resonates a little bit.

Eric Ressler [00:12:20]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:13:05]: Two things. One is that my first instinct was, okay, take a deep breath. You just had a big success. The team really showed up and delivered. We’re in a really good position. It’s okay to just enjoy that and just be in the moment and enjoy that. And so I tried that for a while and that felt good in the sense that there was some rest. I could put more mental, emotional energy into things in my personal life. That was really important. Then I was like, okay, that’s not enough. Maybe what I’m going to do is actually focus on rote tasks. I’m going to just knock out stuff that I know I’ve been needing to do for a while. I’ve been pushing it off and I just want to feel productive. So I’m going to try that. And that feels good, but that’s temporary. It’s...

Eric Ressler [00:13:55]: A quick hit.

Jonathan Hicken [00:13:55]: It’s a quick hit. And so when you list off those three things, autonomy, relatedness, and...

Eric Ressler [00:14:00]: Competence.

Jonathan Hicken [00:14:05]: I think about those things and I’m like, I have those things.

Eric Ressler [00:14:10]: But I’m still not motivated.

Jonathan Hicken [00:14:10]: But I’m still not motivated. So right now there’s a bit of a mystery. Now, the broader fear is I have the sense that this is a natural thing for leaders to encounter, but this is probably also a risky moment in that if I embrace this demotivation too much, we enter a coast...

Eric Ressler [00:14:30]: A coast or stagnation...

Jonathan Hicken [00:14:35]: Period. Stagnation period. And that to me is maybe the thing that’s going to get me out of this. I can’t allow that to happen. And so it’s almost like the fear of stagnating might be the thing that breaks me out. It hasn’t yet, but that’s sitting there making me worried.

Eric Ressler [00:14:50]: Yeah. Okay. So reflections on this. First of all, I remember we just recently did an episode that was something along the lines of don’t coast on your momentum, because you were saying, hey, everything’s humming. Almost like, what do we do? And I think what I’m reflecting on is that actually one of the most effective, but maybe not the most pleasant, motivators is pain. So if you have pain, you’re going to be really motivated to do whatever you need to move away from that pain. It’s a basic human instinct, but it translates up to the org level too. If you’re constantly struggling and you’re not meeting payroll, whatever it is, you don’t have the funding you need to reach your mission, it’s painful and you’re intrinsically motivated to do something about that. To get...

Jonathan Hicken [00:15:40]: Out of...

Eric Ressler [00:15:40]: That. Yeah. So if you’re not in that situation, where there’s no pain, just to put it bluntly, that’s going to be a natural motivational deterrent at some level.

Jonathan Hicken [00:15:55]: The pain is not in my face right now. I can see the pain down the road.

Eric Ressler [00:16:00]: Yes. You can foresee the pain coming if you don’t change something. Yeah.

Jonathan Hicken [00:16:05]: Exactly. Which is the urgency I feel to get motivated. It’s really because of that.

Eric Ressler [00:16:10]: I’m reflecting on a time where I was in a similar position to yours, where things were just humming, the systems were working. We were busy, but we weren’t too busy. We were profitable. There weren’t any major problems to solve. The team was humming and I found myself just detached a little bit. I was like, “This thing’s solved, man. I’m going to go surf more.” And it came back to bite me in the ass hard. And in reflection, and I think we talked about this on a recent episode, that same recent episode about don’t coast on your momentum, you need to take the time to celebrate and to calm down, whatever it is. And I don’t want to prescribe this urgency around it, but at the same time, you have this opportunity now to build from stability. And we talked about this in the previous episode.

So what I’ve done that I found really helpful in these kinds of situations is to go seek opportunities for inspiration, which may not be and likely are not work-related things, but sometimes are. I know that you’re signing up to do a really cool museum-focused cohort. I bet when you go start doing that, you’re going to get all kinds of new ideas. You’re going to learn a lot from your peers and it’s going to just intrinsically motivate you, because you’re going to get back into that imaginative state, or that curiosity state, or the experimentation state. To me, those are the things that create motivation when you have... Again, I’m speaking personally, different people are motivated by different things, but you have a new idea, a new possibility, a new venture, or a new frame of mind or thinking, and then you’re like, ah, a switch flips and you’re like, I could do not that, but this sort of thing that’s related to it.

And then you get excited by this new potential. So I would seek opportunities for inspiration and learning. That’s really what helps for me. If it’s truly about motivation, which I do think we should break down, motivation versus burnout, because I think they’re different.

Jonathan Hicken [00:18:10]: So how do you see those things as different?

Eric Ressler [00:18:15]: I think burnout is a systems-level issue. I’m sure there’s science on this too, but I think it’s more psychological. I think the antidote to burnout is true deep rest, and I don’t think true deep rest is going to solve your motivation issue. I think they’re different. So that’s the distinction to me: burnout is you’ve been pummeled so many times for so long without enough time and energy to recoup that your system just goes into a self-destruction mode, and then you get into overwhelm and burnout and then you lack motivation, but the motivation that you’re lacking is because you just don’t have capacity to do anything. And that’s not what I’m hearing you say.

Jonathan Hicken [00:18:55]: No, no. I feel like I can put in the energy, I can put in the time. Those resources are available to me. So it’s a matter of when I show up with that time and with that energy, it’s almost like this mental block. And by the time this episode comes out, I may actually...

Eric Ressler [00:19:20]: Be through...

Jonathan Hicken [00:19:20]: Through this academy. So that might be the thing. And actually one of the reasons I applied to that program was because of this, right?

Eric Ressler [00:19:25]: Yeah, you felt it.

Jonathan Hicken [00:19:30]: I felt that motivation waning and I thought, well, maybe if I surround myself with people who are doing similar but different things, maybe that’s going to be what brings me out of it. So I’ll report back on how that went.

Eric Ressler [00:19:40]: The other thing I was thinking about, and again, I don’t think this is your situation at all, but what I have seen before, I think the other flavor of this worth mentioning, and I don’t think this is you at all, is when the lack of motivation is actually a symptom of a deeper disillusionment with the mission or the organization. I’ve seen this with leaders where they’re done, it’s over. It’s not even really motivation, or it’s not even like I’ve lost interest. It’s more like I don’t even believe that the work is worth doing anymore. That is a really tough one.

Jonathan Hicken [00:20:20]: Yeah, that’s a scary one. That’s not where I’m at. And I could see then the pitfall of that leader staying in the role because it’s a good paycheck and because it’s stable or whatever, and going into that coast mode. So I still very much believe in the work. And so one of the big problems is I don’t even know where this is coming from. I’m like, I don’t even know the source. And so how can I address it if I don’t even understand it?

Eric Ressler [00:20:50]: Yeah. Another near version of that would be almost like a jadedness, where you’ve been in the space or the org so long, you’re just like, I’ve seen these same cycles over and over and over again. And frankly, I’ve been there at times and I’m sure I’ll be there again, where I’m just like, I’ve been through the same cycles over and over and over again. There are some longstanding problems that we’ve tried to solve 10 different ways and just can’t seem to fix. And that does start to tip you into a little bit of a jadedness. And that’s an equally dangerous place to be, I think. And there’s a whole different set of things that I think you have to work on if that’s really your issue. So I’m just thinking about the different flavors that I’ve experienced of this and seen in leaders that we’ve worked with.

Jonathan Hicken [00:21:35]: It’s occurring to me now actually, if things that are happening outside of work are really playing a role in my demotivation at work. I’m going through some personal stuff right now and maybe that is taking some of my energy away from this work. It sort of begs the question of this work-life balance thing. Maybe even some guilt around stepping away and handling these things in my personal life and taking the time to do that. And I do, I feel like this sometimes. I come in, I’m like, I really should spend four hours on this personal life thing, but I got to be at work. I got to be on. And so I don’t take care of that and then I’m too tired to handle it when I get home. And so it’s just this... I guess maybe I’m in the cycle of, maybe I really do need to take a few days off to go handle this personal life stuff and somehow grapple with the guilt of doing that.

Eric Ressler [00:22:30]: Yeah. This reminds me a little bit of the conversation we had around building culture at work. And I think I brought up my own disillusionment around the current meta culture of knowledge work and just professional work right now, where there are these expectations of speed and availability and productivity and efficiency, and I think AI is definitely not helping with all of this. And it’s not healthy, man. We are all complex creatures. We have needs. Work is important. I believe in work, but also work is not the full story, even if you’re doing important purposeful work. And I will die on that hill. I don’t care how important what you’re doing. I don’t care if you’re the president of the United States, you need some time to step aside and become whole again. And if all you do is put your mind on something 110%... I’m speaking personally again here, but almost all of my best ideas come when I’m not trying to come up with them.

And so there’s this balance that you have to strike and everyone’s got to find a balance. And there are seasons of this. There are grind seasons and there are times where you need to develop a pace that’s a little bit more sustainable.

Jonathan Hicken [00:23:45]: Well, I hope that listeners, especially executive directors and CEOs who are listening to this, A, if you relate to this, you’re not alone.

Eric Ressler [00:23:55]: Yeah, I’m...

Jonathan Hicken [00:24:00]: Not alone. And A, there’s probably not a one-size-fits-all solution here to break out of your phase of demotivation, but hopefully we have unpacked some of the tools and techniques that people could use to get out of it. I need to actually go out and practice some of these things and I’ll let you know in a couple of weeks how I’m feeling. But yeah, I guess it’s just a, “Hey, this is normal, and ride it out.”

Eric Ressler [00:24:25]: Yeah, man. I appreciate you bringing this topic in because it’s one that I don’t think we talk about enough in the professional world, and in the social impact space especially. I’ve seen a lot more about team-level motivation, and even what we’ve put out, but I do think there’s a shame around, “Oh, of course I should be motivated.” So hopefully this is a good conversation starter for the sector and for leaders to just realize, “Hey, we all go through this in different ways and we can start to share some tips around how to get out of it and how to...” Get out of it isn’t even the right way of saying it, but just how to accept it and embrace it and work around it, so to speak, and know that you’re going to come back out of it and hopefully have some tools to be able to do that in the right time.

Jonathan Hicken [00:25:05]: This is one where I really want to hear from listeners on if they’ve experienced this, and if they’ve done anything that worked, to share it, because maybe this is an opportunity to destigmatize a little bit this feeling that we have. But thanks for rapping with me on this one.

Eric Ressler [00:25:25]: Yeah, man. Thanks for bringing it to me. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Plenty of people still picture a museum as a quiet building with art on the walls, a ticket desk at the door, and a staff whose job is to guard what’s inside. Victoria Munro thinks that picture is out of date, and she also sees an advantage in it. Because the outside world assumes museums are harmless, they have a lot of room to do serious work on social change and safe space.

Victoria is the Executive Director of the Alice Austen House in New York City. Originally from New Zealand, she came to the US at 21 to study, moved from sculpture into photography, started an artist-run gallery early in her career, and later earned a master’s in arts education. She’s also board president of the Museums Council of New York City, which brings together more than 120 institutions of every size.

When she arrived ten years ago, the museum was interpreted as a historic house, filled with period furniture that never belonged to Alice, and the rooms were roped off so a class of fourth graders couldn’t even walk inside. All the while, the museum held more than 8,000 photographs by its namesake, a lesbian photographer who took 50 pounds of equipment onto the streets of New York on a bicycle in the 1880s and built safe spaces for her largely queer circle of friends. Victoria took the ropes down and let Alice’s own work tell the story.

That history shapes how the museum operates today. As a nationally designated site of LGBTQ+ history that looks, from the outside, like a small house in a waterfront park, it can offer programs people join without outing themselves. Victoria designs programs people come back to until they’re co-creating them, and she takes programming out into the park for families who don’t feel welcome in museums yet.

She and Eric also get into why so many art lovers hesitate to call themselves creators, why a yearly budget should be aspirational, and why the reflection that keeps a leader going can’t happen alone.

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Episode Highlights:

[00:01:55] From sculpture to photography: portability, personal archives, and the family snapshot
[00:04:25] Why a background in education makes for a stronger museum leader
[00:07:20] Museums as sites for contemporary connection
[00:08:55] The yearning for in-person experiences people can take home
[00:10:55] Why art lovers hesitate to call themselves creators
[00:11:25] “Sneaky” programming that turns visitors into co-creators
[00:12:40] A safe space that doesn’t look like one: LGBTQ+ history in a historic house
[00:13:45] Programming for people who aren’t ready to cross the front door
[00:16:20] Taking down the velvet ropes at the Alice Austen House
[00:19:45] Alice Austen, one of the first women to take photography onto the street
[00:30:20] Budgets, strategy, and leadership as creative acts
[00:36:55] Staying motivated through professional community

Notable Quotes:

[00:07:20]: “We need to look at museums as being not just repositories of historical collections, but being spaces that are sites for contemporary connection.” Victoria Munro

[00:13:05]: “Coming and participating in one of our programs isn’t going to out you.” Victoria Munro

[00:17:00]: “Really, what was that chair saying to that fourth grader? Nothing. Absolutely nothing.” Victoria Munro

[00:30:20]: “Your yearly budget should be aspirational. It should be based in reality, but there should be things that you are aspiring to.” Victoria Munro

[00:33:14]: “Maybe one of the most important elements of creativity is imagination, the ability to imagine something that isn’t yet here.” Eric Ressler

[00:38:15]: “You can’t do all that reflection on your own. You’re not going to be effective at reflecting all by yourself.” Victoria Munro

Resources & Links:

• Alice Austen House — the museum Victoria leads, with event listings and information on Alice Austen’s archive of Victorian photographs

• Museums Council of New York City — the association of NYC museums where Victoria serves as board president

• Victoria Munro on Instagram

• Alice Austen House Instagram

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:05]: Victoria, thank you so much for joining me today.

Victoria Munro [00:01:10]: Oh, it’s such a pleasure to be here.

Eric Ressler [00:01:15]: So I think where I’d like to start today is to dig into your experience both as a museum curator, now a museum executive director, and specifically a lot of experience around photography as an art form. And I would just be curious to hear your point of view, your take on how all of those different elements, both museums, photography as an art form, and your experience as an executive director, have informed your point of view on the role that that art form and museums in general have to play in the broader social impact ecosystem.

Victoria Munro [00:01:55]: Well, that’s huge because there’s several topics in there. I came to photography back in the 1990s. It was when I first came to America, actually. I’m from New Zealand originally, and I came over to the States when I was 21 to study. And I was making sculpture at the time, and it suddenly didn’t feel like a very transportable medium. It wasn’t making a lot of sense to me, but I was also at the same time really digging into all of the facets of photography from a more philosophical standpoint and doing a lot of reading and research around the way humans adopted photography so quickly and this idea of an accessible way to create your own personal archive, and all of these autobiographical stories that were happening and family histories around photography. Plus at that stage, digital photography was still not widely adopted and I didn’t have a smartphone or anything like that. And I was completely fascinated by the sheer volume of photographs that were being developed worldwide every day and the endless possibility to multiply that in itself. Everything became a copy. And so it was part this idea of memento, also traveling, being away, portability of an art form, and then the way in which photography has become such an important tool for documenting our past.

So I was really fascinated by that. And very early on in my career, I started an artist-run gallery, so instantaneously walked from being in art school to curating exhibitions and traveling with the exhibitions. And so after many years of making work, I also along the way got my master’s in arts education. And I think in terms of leadership, having a really, really strong, solid background in education is crucial for designing programs, understanding the materiality and the reach and the impact of programs. But also when I talk about education as a tool for leadership, it really helps you to work with staff at all different levels of their career and really think deeply about how you might foster learning within the workplace. It shouldn’t just stop at, you have a position description now, here you go. No, no way.

And then on the museum side of things, so yeah, we’re talking about this history of curatorial work, that also leans into a really deep passion I have for supporting artists. As an artist myself, I understand the struggle and the barriers that there are to potentially getting representation or just getting eyes on your work. And one of the most helpful things for me was being asked to lecture in a program that was around professional practice for art school students, being there and talking with them about how the dealer gallery is not the be-all and end-all. The big show is not. How do you create other ways to be seen? What is a gallery? It could be a zine. It could be something as simple as you’ve gone to, I’m going to sound old, Kinko’s and Xeroxed off a whole bunch of work and distributed it for free. You have to think outside of the box and you have to be scrappy and prepared to say, “I’m going to put in my own time and my own effort, but then hopefully find collaborators out there.” And so the key within this environment of being an executive director, I feel, is that multi-tiered role of being able to support staff, artists, your contributors, the broader community and other organizations, as being that highly collaborative model that is going to be an awesome tool for you.

And also as a lifelong learner, that’s really going to feed your practice in so many different ways and it’s going to keep you motivated. And I do think that we need to look at museums as being not just repositories of historical collections, but being spaces that are sites for contemporary connection within that storytelling of what is history. It gets dormant if it’s not activated by an intergenerational group of people coming in and benefiting from it, which we could talk a lot more about, which is what I’m really interested in, is how museums can actually be a force for change.

Eric Ressler [00:08:05]: Well, let’s stay on that thread then for a little bit. And it sounds like this is something that you’ve thought deeply about, and I’ve been thinking more about this also in the current state of the social impact sector, movement, whatever you want to call it, where there seems to be culturally a magnetism back to in person, back to gathering in person, whether that’s through cohort-based learning or offsites or professional development opportunities, all the way through just this cultural yearning for the return of some kind of third space in our culture. So what are your thoughts around the role that you see museums playing? How are you thinking about that as an executive director of a museum? What’s on your mind there?

Victoria Munro [00:08:55]: Well, I think for one, yes, there is a great yearning for that in-person connection. I think that everyone has become extremely exhausted from consuming so much of culture online, but also consuming, period. And so there’s this much greater desire, again, to have what it is that you’re consuming be the experience. And a lot of that really meaningful experience happens in person. And so creating programs that are able to activate that. I love it when there’s programs that happen in museums that people also have a take-home product. It’s something that they’ve actually been able to create themselves.

Eric Ressler [00:09:55]: That strikes me as an interesting two sides of consumption and creation, and they often reinforce one another. And I think about my own various journeys as an artist in different forms and most specifically around music. When consuming music, it inspires creation. And then the act of creating music inspires me to want to consume more and learn from some of the greats and get inspired by other people. I think this is just inherent to being part of an art scene. What I’ve noticed, and this is something I haven’t personally struggled with just because of the nature of my essence as a human, I guess, but I know a lot of friends who are avid consumers, but they’re almost afraid, or there’s some kind of block to identifying as a creator. They don’t seem to be able to make that leap. Why do you think that is?

Victoria Munro [00:10:55]: I think that people have a lot of insecurities around being able to feel like they’re a part of an arts community, and so they feel a degree of comfort saying, “I’m at the level of...”

Eric Ressler [00:11:05]: Supporter.

Victoria Munro [00:11:05]: Or listener, viewer. It goes back to part of the first part of the question and thinking more broadly about the roles that museums play in people’s lives. And I think that it’s an interesting area because you can actually be quite sneaky with your programs. And I do like to say it’s a little sneaky. You actually are having someone becoming involved with a program, and maybe it’s a program that they can also revisit, come back to. It’s multi-tiered, it’s quarterly or something like that, kind of offering at the museum. And before they know it, they’re becoming a creator. They’re co-creating the program.

But on another level, what I like to talk about is there’s ways in which the outside considers what a museum does and what you can actually do with your programming that is quite wild, because there’s an assumption that we’re just historical gatekeepers or just putting these shows on the walls and charging admission. It allows you quite a lot of freedom to do quite a lot of important work within social change and creating safe space. So of course the museum that I currently am the executive director of is a nationally designated site of LGBTQ+ history. But from the outside, we look like a small historic house located in a very picturesque waterfront park. So coming and participating in one of our programs isn’t going to out you. It’s not going to be a scary step over a threshold of potentially a pride center, which of course, all of those things are really important spaces and places, but you are able to participate as an ally or as a queer person in this totally safe space.

And that’s really, really important to me. Obviously for some communities that haven’t historically felt welcome in museums, there’s another whole tier to inviting those communities. And I believe that a lot of that can also take place by not having an expectation to cross the threshold of the front door. So what are you doing in other ways where you are collaborating with other community groups? Or if you’re fortunate like me, I have a public park, so I’m able to activate the outdoor space without entering into that with an intention of making someone visit my museum. No. How am I going to provide a program that would be beneficial for someone who doesn’t necessarily feel welcome in museum spaces or has fear around them, but with the hope, obviously, that one day you can break down some of those barriers for that family? So doing that in all different ways with programming that’s beyond the museum walls.

Eric Ressler [00:14:55]: My sense in doing some work with museums and just observing the space is that there’s been a trend, almost a reinvention of the role museums and place-based organizations, especially social impact focused organizations, can offer outside of the traditional, maybe even reductionist view that museums are just places to put art on walls and charge admission fees to come participate in, and that’s the extent of it. What’s your view around what’s changed, or is that just a misunderstanding of what museums have always been, to think of them that way?

Victoria Munro [00:15:40]: No, I think it has changed. I really do. I think historically, and there’s still some museums operating in this way, there’s a more elitist culture around museums and an assumption that those who visited museums were art historically trained or had the ability to appreciate what was on the walls, rather than this role of saying, we have something wonderful that you may want to see and engage with, but we are going to really think deeply about what’s going to make that or activate that engagement.

So when I started 10 years ago with the Alice Austen House, it was presented as a historic house. It was filled with historic furnishings and there were roped-off rooms. There was no way in which you could have a class of third, fourth graders come in, even physically, into those spaces. And to me, obviously I love historic things. I think historical furniture is wonderful, but really, what was that chair saying to that fourth grader? Nothing. Absolutely nothing. I wanted them to be able to walk into the rooms. You have this architecture of the historic space that is giving that very place-based experience. But if you can’t walk inside and be a part of it, that’s going to be very difficult for you to connect at all or feel welcome. Velvet ropes, I don’t like them.

Eric Ressler [00:17:35]: Yeah, they don’t feel very welcoming. Yeah.

Victoria Munro [00:17:40]: Yeah. So how do we think differently about interpreting some of these collections? Perhaps we put less on show, we allow people to walk around them. I also don’t necessarily think that recreating a historic room is necessarily the best use of a museum space. And that’s where that fortunate element often of photography, or even painted, some kind of documentation of what it was like, you don’t have to do a historical reenactment to bring it to life. Please do not have your staff wandering around in pilgrim clothes. That very rarely is going to work. There’s certain things like engaging in maybe some candle making or butter churning that will be really, really fun for the audience because they are participating. But then again, wow, am I so fortunate? I have a bank of 8,000 or more photographs and a namesake of this museum for whom this home was her muse. It was her studio. And so she documented it over and over again. But why, only 10 years ago, was it being interpreted with furniture that wasn’t even hers? Yes, it was period, instead of just using the photos.

Eric Ressler [00:19:05]: They tell the...

Victoria Munro [00:19:05]: Story.

Eric Ressler [00:19:10]: Through her lens too.

Victoria Munro [00:19:10]: Absolutely. Through the lens of a lesbian woman who was an absolute badass. And this is super cool, all of these things that our namesake did to create safe space for her and her largely queer circle of friends, and documented it. It’s amazing. I need the space to show that.

Eric Ressler [00:19:40]: Yeah. And please correct me if this is wrong, but in doing research for our show today, I understand that Alice Austen was potentially the first female street photographer to exist. Is that true? To take the camera out of the studio setting, which was very unheard of at her time?

Victoria Munro [00:20:05]: Yeah, one of a handful of women at the time. So just to be really clear, there were women and there was encouragement for women to enter into the field of photography, but it was all studio based. It was really thought that women had a much more sympathetic way about them to photograph children and create these images of motherhood and femininity. And Alice was taking upwards of 50 pounds of photographic equipment onto the streets of New York City in the 1880s and ‘90s on a bicycle, and obviously was just an incredibly confident person because she had to win the trust of her subjects. It’s not like you could take a snapshot incredibly quickly. But yeah, there was no genre or field of photographic journalism at the time. So yeah, she’s a true, especially for women, a pioneer of the medium in this way, in a very social way, and was also hired on assignments to document the quarantine stations on Hoffman and Swinburne Islands, which people don’t even learn about. They only hear about Ellis Island during a time when immigration was at its all-time high in New York City.

Eric Ressler [00:21:35]: Right.

Victoria Munro [00:21:35]: Yeah, it’s really incredible.

Eric Ressler [00:21:40]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

So how do you think about, as a curator, as a program designer, that balance of celebrating this rich history, this view into a different time, a different way of being, a different social circle that’s very, very unique, but also very relevant to our time right now, and also tying that together in a way that doesn’t feel like that exclusive gatekeeping version of what a museum can sometimes be or has been in the past?

Victoria Munro [00:23:05]: Well, you said it. It’s relevant now. So the example that Alice and her work left us was pretty phenomenal. So if we follow the themes in her work and her life, they’re super relevant today. It’s a riches-to-rags story. She ended up in the poorhouse.

Eric Ressler [00:23:35]: That’s right.

Victoria Munro [00:23:35]: Stripped of all of her possessions, separated from her life partner, Gertrude Tate, by poverty, and then eventually by some homophobia as well. She died in 1952, so it was hardly in the era that we could call progressive. In fact, I’d like to think she had more freedoms in the 1890s, because women were thought not to have a sexuality at the time. But yeah, there’s all these incredible themes in her work and parts of her story. She also grew up fatherless. So the Austen family was this large extended family that then also included some Irish maids and then all these animals. And so all of them I like to include on the family tree, because it’s much more a reflection of the way we live our lives now. But Alice set up all of these clubs that were safe spaces, and so we take that as the grounding model for the museum, that it is the safe space that she tried to foster and create. But then all of these themes in the work feed into the contemporary, mostly photographic arts programs. So no matter when you visit the museum, there’s a high-level contemporary exhibition on view, and all through the summer there’s outdoor photo exhibitions that are really providing a platform for more emerging artists at the same time. Yeah.

Eric Ressler [00:25:05]: You mentioned that you got your start as a sculptor and then moved to photography. Are you still shooting right now?

Victoria Munro [00:25:10]: Sculpture again.

Eric Ressler [00:25:15]: Sculpture again. Oh, nice. Full circle.

Victoria Munro [00:25:20]: Yeah. I have an art practice that is always informed by photography. It’s very interesting. But I like to take a medium, and I’m also very interested in painting as well, and see how that informs my sculpture. So there’s all these intersections between painting, photo and sculpture.

Eric Ressler [00:25:55]: Yes.

Victoria Munro [00:25:55]: And my sculptures are mostly wall-based. They mimic a lot of the forms and functions of painting. I’ve often made a lot of sculptures that are endlessly replicable. They’re all multiples. So the photography is always there, although I do have a new photo project that I would love to work on. It just hasn’t quite found its feet yet because, guess what? I’m very busy. It’s always the dream, right?

Eric Ressler [00:26:35]: Yeah.

Victoria Munro [00:26:35]: It’s like I could do it. I could support all of these artists, plan all of these exhibitions, because I absolutely love curating, and make my own work. And so my own work does tend to very much be on the back burner a lot of the time, although it’s not this year. I have a solo show coming up.

Eric Ressler [00:26:55]: Awesome. Congratulations. Yeah. Thank you. I resonate with a lot of that as a photographer myself. Across all the different artistic hobbies and interests that I have, photography is the one that is the most temperamental, in the sense that I will go years sometimes without picking up a camera that’s not my iPhone, and then I’ll have years where I shoot every day. And it’s just about what’s happening in my life and what I’m inspired by. And sometimes all it takes is stumbling upon just an incredible photograph that reignites that creative energy in me. It’s like, what am I doing? I need to be out there shooting. And I’ve gone through various phases professionally of shooting for commercial purposes and for our clients, which then usually leads to me not wanting to shoot as much for fun or as a personal passion. And then I’m also reflecting on what you said about the nature of how you see everything through that lens of photography.

And as I’ve explored various creative mediums professionally through design, also through photography, through music, and others as well, I’ve started to see all those different forms of creative expression as just, they’re all from the same root in my brain. And I think there’s this amazing cross-learning that happens, and I even think about this in music from one instrument to another. Me playing bass makes me a better keyboard player. Me playing keyboard makes me a better bass player. I think the same is true between painting, photography, sculpture, because you’re building that muscle and then you are inspired and applying it in different ways. And so I guess my point and then my question is, creativity seems to be a muscle just like anything else, and I don’t expect everyone to develop that muscle in the same way. Other people have interests that I don’t have that I’m sure are just as fulfilling for them, and interests or callings even at a deeper level.

But to me, I’ve learned that if I don’t have time in my life to give myself that creative time, I’m just significantly less happy as a person. And I feel this urge to embrace that and to share it and to invite other people to find what their version of that is, because it’s such an important part of, in my opinion, the human experience, and it gives people the opportunity to then go and share. So how do you see that in your own work, and how do you bring that to other people in this participatory framework and programming that you have at the museum?

Victoria Munro [00:29:40]: Well, that was a winding question, and I kept on having all these ideas while you were talking, and I was like, “Well, there’s that and there’s that.” And I think that it’s incredibly important within leadership and program development to be highly creative. As a museum leader, you’re a strategist and you’re writing budgets, but you need to be. A lot of these things that sound incredibly boring about the back end of your work aren’t actually, because they are visionary and creative and aspirational.

Eric Ressler [00:30:15]: Yes.

Victoria Munro [00:30:20]: Your yearly budget should be aspirational. It should be based in reality, but there should be things that you are aspiring to. I want to put on that program. It hasn’t been funded yet. I know I’m going to find that funder that sees the value in this. You’re creative with your marketing, with your outreach. It’s all really essential.

And then if we come back a little bit personally, all of these intersecting mediums that I work across in my own personal art practice, they all come from a root. I’m very conceptual as an artist. So a lot of people are very, very passionate about vernacular photography or street photography or more like photojournalism. I’m much more conceptual when it comes to my approach to photography, and that’s how it intersects with the other work that I make. I think often people are surprised by my work when they see it. They’re like, “Oh, this is really conceptual.” And I’m like, “Yeah, I’m not actually running around outside with a camera. If I’m going to be shooting, I’m actually setting it up. It’s studio based. It’s very controlled.” But all of these ideas around vernacular photography and the photography of the everyday are inherently important to informing what it is that I’m creating.

So I think within the museum field, even if you’re running a science museum, it doesn’t matter the medium of the museum. It’s so crucial that you and your staff have the ability to be very creative. And we’re working at a time where it’s not just technology that’s changing so fast. Politics is changing so fast. What is supposedly able to be funded is changing so quickly. There’s also many communities that are at risk. And it’s not just about being nimble, it’s about being really creative around the ways that you can still work for and support those communities and have your institution be a true anchor for your community.

Eric Ressler [00:32:55]: Yeah, I love a lot of that. And I think even in an effort to not gatekeep what it means to be creative, I love how you are thinking about the annual budget as a creative act. And the other thing I’m reflecting on in your answer that resonates with me is that maybe one of the most important elements of creativity is imagination, the ability to imagine something that isn’t yet here. And I think that’s a lot of our work in this space, is to imagine what might happen, what might be true, what would we need to do to get there. And a lot of that is an imaginative muscle that, even if you don’t identify as a creative person, maybe you’re not out sculpting on the side, but you’re still being really creative in your strategic planning, in your programming, in your cultural design for your institution.

To me, that’s almost a prerequisite of any kind of meaningful social change at any scale, whether that’s small and local and place-based or systems level. It comes back to some idea, some imaginative state that then allows you to think what else might be, and then reverse engineer how might we get there. So I appreciate your perspective there. That deeply resonates with me. And I hope that listeners can take away, even if you don’t identify as a creative person, if you’re in this work, you probably are a lot more creative than you’re giving yourself credit for, even if it’s not the traditional forms of creativity.

Victoria Munro [00:34:35]: I think also managing a staff and inspiring a staff, inspiring them to feel really motivated to be with you, aside from offering them obviously really human working conditions and having them feel valued and all of those things, is also another part. It’s not just the person that’s walking in the museum, it’s your staff that are out there and living their lives and coping with what is the changing environment too. And so having the ability to think of creative ways to keep them inspired and also have them be co-creators in this environment is really key. And yeah, absolutely, you do not need to be that person that comes home and starts on a major artistic pursuit, because the point is that we all have very creative abilities, and it’s just recognizing what it is that is your creative superpower and giving yourself some time and some acknowledgement for how great that is that you can do that. We all have different skill sets that we bring to the table in our leadership, but a lot of them do have very creative roots, and that’s fantastic.

Eric Ressler [00:36:05]: Before we wrap up, I’d love to ask you a couple things. You mentioned the last couple of years especially, there’s so much changing in the sector politically, the funding landscape, the issues directly related to your work. How do you, as a busy executive director who also has a full life outside of that role, it sounds like, especially from an artistic side, how do you stay motivated, stay in community in the work, especially at times where it can be challenging or feel like the odds are stacked against you or things just aren’t breaking your way?

Victoria Munro [00:36:50]: Friends.

Eric Ressler [00:36:50]: Friends. I love that answer.

Victoria Munro [00:36:55]: I’m also the board president of the Museums Council of New York City. It’s 120-odd institutions that range from the big to the tiny. And we have four very collegial meetings that myself and our other board members organize per year at various member institutions. And coming together with those folks, and they’re at all different levels, it could be a front desk visitor services person to an executive director that comes there, and talking with them is incredibly healing. Even if we’re not all talking about problems or something, it’s inspiring to hear about what their programs are, what the share-out is. So creating some moments in the professional community is, I think, incredibly key, because they understand. Even if their role is quite different or their museum collection is very different, there’s much more of a shared understanding there. So that collegial part of things was so much in my education training. You are supposed to take time to reflect...

Eric Ressler [00:38:05]: But...

Victoria Munro [00:38:10]: You can’t do all that reflection on your own. You can’t. You’re not going to be effective at reflecting all by yourself. And as an artist too, you need to talk about your work. So finding spaces, I think, collegial spaces that you integrate into your actual social network, are very, very helpful.

Eric Ressler [00:38:40]: I think that metaphor is really intriguing to me, as an artist publishing, getting into the gallery or whatever that looks like. It doesn’t have to be a gallery, but I write a lot of music and my audience is the 10 friends that I text it to. But even that feedback loop is so much more meaningful than it just being only me experiencing that. And I think there’s a similar thing that happens in the professional world. And I agree that when you can do that with your peers, regardless of their role and the scale, but just another cohort of folks who are doing something similar-ish to you, that’s where I think some of the most generative, inspiring ideas come from in my experience. So I love that answer. Victoria, where can our listeners learn more about you and your work, both personally and professionally? What do you want to plug here for our listeners at the end?

Victoria Munro [00:39:35]: Wow. Okay. I guess I’m on Instagram at Victoria_Munro, and Munro is spelled M-U-N-R-O, so people often get caught up by that. I’ve got the old Scottish spelling. And I’m always posting in my stories about the Alice Austen House, and I post about the exhibitions because they are so close to my heart and my artistic practice. And then a website is a work in progress at the moment. And then also just the Alice Austen House website. It lists all the events. It’s got a ton of information if your interest is piqued in this incredible archive of Victorian photographs. And that’s just at aliceausten.org, and Austen spelled A-U-S-T-E-N. So I would say those are great places to start. And yeah, I’m very accessible. My email’s on the website. You can always DM me on Instagram. Honestly, I love building and growing professional community. I think that that’s absolutely key.

Eric Ressler [00:40:35]: Awesome. Victoria, thank you so much for your time today. Next time I’m in New York, I’m hoping we can meet up and I can come do a tour. But nonetheless, thank you. This was great. Really appreciate it.

Victoria Munro [00:40:50]: It was great too. Thank you so much. It was lovely to talk.

Eric Ressler [00:41:00]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Most teams in social impact are more experimental than they get credit for. They test, they iterate, they build a hypothesis about how to reach the people they serve and adjust when reality pushes back. The sector already borrows from the scientific method and from design thinking, whether or not anyone names it that way.

I have watched hundreds of these teams up close. The place I keep seeing the borrowed methods break down isn’t the experimenting. It’s what happens after something doesn’t work.

Science made its peace with this long ago. A failed experiment carries as much information as a successful one, and researchers publish both, so the whole field gets smarter from what didn’t pan out. The sector almost never does. Jonathan can’t think of a single blog or talk called “I tried to solve homelessness and I totally failed.”

The reasons are structural. Admit failure to your board and your job can be on the line. Tell a funder a program didn’t work and you risk the funding stream a dozen livelihoods depend on. So the failure gets reframed as a learning, smoothed over for the annual report, and the insight that could have helped the next org in the sector disappears.

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Science built failure in and rewards the people who report it honestly. Social impact built the opposite, and it treats a lost grant as a kind of moral failing in a way a startup burning venture money never would.

Design thinking gets the same pushback lately, and I want to defend it. It was built for these messy, wicked problems, the ones with no clean answer, to get teams out of endless planning and in front of the people they serve with something real.

The throughline is discernment: knowing which failures you can afford and which you can’t. You can fail on the format of an event; you cannot fail at getting food to the person who needs it.

So the question this episode leaves open is one I haven’t answered for myself. Whose job is it to change this, and what would the sector look like if we let ourselves say out loud what didn’t work?

Episode Highlights:

[00:01:00] The lab: kicking an idea around about the scientific method
[00:03:30] Defining design thinking and the scientific method, side by side
[00:04:30] Where the two frameworks overlap and where they split
[00:06:00] Mapping both onto how the sector actually works
[00:08:00] The real failure point: we won’t admit when things don’t work
[00:09:30] Funders, boards, and the pressure to hide what failed
[00:11:00] How science learned to publish its failures
[00:14:30] The scale of failure and when it’s safe to name it
[00:18:00] A closed-door conference where funders aren’t invited
[00:20:00] Building a team culture that works with failure
[00:22:30] Why the sector treats a lost grant as worse than startups burn funding
[00:24:30] In defense of design thinking
[00:27:00] Experiments and pilots run on different timescales
[00:29:00] A small, real example of design thinking at Cosmic
[00:31:00] Knowing where failure is okay and where it isn’t

Notable Quotes:

[00:08:25]: “Failure of an experiment is just as valuable as the success of an experiment. In fact, those words don’t really even map to science, because simply executing the science soundly is success.” Jonathan Hicken

[00:09:45]: “You don’t want to tell your donors you messed up and you failed. But that’s the trap. That’s the irony: we actually do, especially at a sector-wide level, need to be real about what works and what doesn’t.” Eric Ressler

[00:10:40]: “If I tell a funder that this didn’t work, then I’ve just risked that funding stream, and I’m supporting a bunch of people in their livelihoods that I don’t want to put at risk.” Jonathan Hicken

[00:16:45]: “We have to avoid the common gravity toward reframing failure as a good learning or a win in a way that diminishes the true insight we can get from admitting it didn’t work.” Eric Ressler

[00:20:35]: “If we accept going in that some things won’t work, then there’s no shame in naming it when it happens, because it’s there.” Jonathan Hicken

[00:32:00]: “The questions to ask are: what are the stakes of failure for this experiment, and who carries the burden if it fails?” Eric Ressler

Resources & Links:

• You Design Your Culture. Here’s How : Designing Tomorrow Podcast Episode from August 18, 2026

• Stanford Social Innovation Review article on design thinking and evidence — mentioned at [00:03:00].

• IDEO U — design thinking courses, mentioned at [00:26:30]

• Stanford d.school — design thinking courses, mentioned at [00:26:30]

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:55]: All right, Jonathan, I’ve got this thing kicking around in my brain that I need to tease out with you on the podcast, so it can get out of there and start to become a little more real.

Jonathan Hicken [00:01:05]: This is one of my favorite kinds of these episodes. It’s one where we just kick around an idea.

Eric Ressler [00:01:10]: It’s the lab. It’s the lab here for my brain. So lately I’ve been thinking a lot about the scientific method. Don’t ask me why. As I work with teams, one of the things I’m endlessly curious about is how these people think about doing their work every day. And what’s really cool about being in my position is I get to see that from dozens of different vantage points a year, if not more. At this point, hundreds of different teams at different stages, doing different work in different niches in the social impact space.

What I’ve noticed is that a lot of teams use elements from the scientific method, mostly experimentation, iteration, developing hypotheses around how to do their work. And I’m well versed in some of the design thinking frameworks and methodologies given my background as a designer, and there’s some overlap between those two. I want to dig into both. And I want to talk to you specifically about this, given that you’re in a role at a science center, and a lot of the way you run your shop is based in some of those principles of science too. So that’s my topic for today.

Jonathan Hicken [00:02:30]: And tease out: what can we learn from design thinking or the scientific method that could help social impact perform more optimally? Or where are we failing when it comes to executing on our work? Is that the idea?

Eric Ressler [00:02:45]: What should we take from those? What should we leave from them? Because there’s been some criticism, some of it fair, around design thinking not actually fulfilling its proposed promise as the best approach to social impact and solving wicked, intractable problems.

Jonathan Hicken [00:03:05]: And there was an article out of the Stanford Social Innovation Review recently, basically saying, “Hey, we’ve collected all this evidence on all this stuff. Why aren’t the results better?” There’s also a little bit of a knock on the scientific method right now as well.

Eric Ressler [00:03:15]: Exactly. So let’s dig in, because I think both of these frameworks have some validity, and I have my own hypothesis around where we are not actually being very scientific in this work.

Jonathan Hicken [00:03:30]: Let’s define these two ideas to begin with, design thinking and scientific method. I’ll start with scientific method. The simple version is: I have a question about the world. I develop a hypothesis about what I think is happening. I observe, I measure, I test in a way that others could replicate. I publish it, whether or not the hypothesis was correct or incorrect. I get it out into the world. Maybe I do another experiment, maybe somebody else does, but I’ve contributed that knowledge to the knowledge base of humanity.

Eric Ressler [00:04:05]: And my take on a simple articulation of design thinking is essentially understanding or identifying a problem, empathizing with the people most affected by that problem through listening, developing quick prototypes and testing them with those same people, learning from those prototypes, iterating, and ultimately building toward a solution.

So there’s a lot of overlap between the two frameworks, but there are also a couple of distinct differences worth pointing to. Science is working mostly toward understanding and being able to generalize that understanding, to replicate it, to reduce bias, to design things so it’s as controlled as possible. Design thinking embraces the constraints and doesn’t try to create something replicable so much as something custom built for that particular situation, with a goal of solving the problem specifically. So in my mind these are two potentially helpful frameworks or toolkits that we should be pulling from in this space.

Jonathan Hicken [00:05:15]: And what’s similar between them is there’s a problem, there’s a certain level of activity that you do several times until you get it right. And what’s also similar is that you eventually ship something.

Eric Ressler [00:05:25]: You ship something. And they’re both trying to solve a problem of uncertainty. You’re uncertain about what the right solution’s going to be in the case of design thinking. So you embrace that uncertainty and you try to get out of thinking and into doing. The big takeaway for me around design thinking is that you can intellectualize something forever, but until the rubber actually meets the road, you don’t really know. So shipping and getting stuff into the real world and iterating from there.

And on the science side, it’s really about testing your understanding of something, again through applied science, through research, through the real world and real results. Now, of course there’s theoretical science and other types beyond that, but when we’re talking about applied science and the scientific method, it’s really about material stuff in the real world.

Jonathan Hicken [00:06:20]: Let’s map that to social impact then. So we as founders or executive directors or people in the space, generally speaking, we see a problem, we devise a solution, and we implement it, hopefully for the purpose of some positive results for the world. So where are we not lining up with design thinking or the scientific method, in your estimation?

Eric Ressler [00:06:50]: Going back to the beginning of the episode, where I’ve been in this position to see a number of different teams, I’d say there are different levels of adoption. Most teams aren’t sitting there thinking about how they’re going to use the scientific method to do their work. Now, sometimes they are. We’ve worked with organizations that are literally doing science. But not all orgs are leaning into this at that level of depth.

I do think generally the space tends to be experimental. Given that these problems are wicked, complex, intractable, there’s usually not just a proven, known solution. And if there is, it might not work in the same community you serve. So there’s that uncertainty piece. We’re not certain how we should best solve this problem. So we either need to guess or we need to test, or some combination of the two. What I see is a lot of teams being willing to experiment. Not all teams, some are stuck in their ways, and even that feels kind of scary. Where I think we fail the most in the principles of both the scientific method and design thinking is being willing to admit and learn from failure. That’s what I’ve observed.

Jonathan Hicken [00:08:20]: And that’s fundamental to the scientific process. Failure of an experiment is just as valuable as the success of an experiment. In fact, those words don’t really even map to science, because simply executing the science soundly is success. So where I think you’re getting at is, especially as it relates to impact metrics, end-result metrics: where are we as a sector allowed to name that failure for the purpose of the collective understanding of how to solve these problems?

Eric Ressler [00:09:05]: So let’s practice a little design thinking here in real time and have some empathy for people like you and others in the social impact space who wake up every day and are passionately, sometimes thanklessly, working on really difficult issues, not always in the best situations. To ask them to do that work their best, tirelessly, fail, and then tell the world they failed. You see why this doesn’t happen.

And then when you start to consider the power dynamics of funders and these organizations, whether those are institutional funders or high-net-worth individuals or family offices or even everyday folks contributing, you don’t want to tell your donors you messed up and you failed. That’s not a thing you want to do to build confidence and a strong reputation of being an effective social impact organization. But that’s the trap. That’s the irony right there: we actually do, especially at a sector-wide level, need to be real about what works and what doesn’t and what we learned from that. And that’s just a really tough tension that is systemic in nature and complex to get through.

Jonathan Hicken [00:10:15]: You could bring that down all the way to the individual motivation level. You’ve got an executive director or whomever who, in my case, would be like: if I go to my board and I admit failure, my job is on the line. That’s my family’s wellbeing on the line if the board misinterprets what I’m bringing to them. And then you scale that up to the organizational level: if I tell a funder that this didn’t work, then I’ve just risked that funding stream, and I’m supporting a bunch of people in their livelihoods that I don’t want to put at risk. So there’s an inherent contradiction in admitting failure. But that’s a real problem for the sector, if we’re learning all these things and we’re not talking about them.

Eric Ressler [00:11:05]: And this is what I’ve been spinning around in my brain: how did science get over that? Because science did, overall. Let’s think about drug science as maybe the closest parallel, where a lot of money’s on the line. You’re doing drug trials with the hope that your drug cures the disease. And maybe if you fail, maybe you do get fired if you’re the lead researcher or the lead scientist. I’m not deeply versed in that world. But my sense is that overall, science as a field has done a better job of building in and embracing failure, and scientists publish their failures in journals that other scientists read. And we do that a little bit in the sector, but not even close to the same level.

Jonathan Hicken [00:11:50]: Yeah, I can’t think of a single article or blog or video I’ve seen that was like, “I tried to solve homelessness and I totally failed.”

Eric Ressler [00:12:00]: I’ve seen a couple like that, to be fair, but they’re pretty rare, and they’re definitely the edge case and not the norm.

Jonathan Hicken [00:12:10]: And they’re probably people for whom the risk of putting that out in the world is gone or diminished in some way. Now I’m speculating, but maybe people who have moved past the sector or into other roles, where being so blunt isn’t such a risk.

Eric Ressler [00:12:30]: Well, the other thing there, reflecting on the articles I’ve read, they’re usually from institutional funders. Part of me is like, that’s good, they should be doing that. That’s part of their job, to make these investments, these bets on impact, work with practitioners who are on the ground and know this stuff really well. And they’re in a unique position to publish what worked and what didn’t. But then I see a counterargument too: what if one of those folks publishes something with a really credentialed, high-reputation take, like, “oh, this intervention doesn’t work.” But actually it just didn’t work that one time, and now everyone else whose business is built on that intervention suddenly struggles.

So I want to acknowledge, I see how we got here as a sector. And yet I keep coming back to: this is holding us back in a major way, and I can’t quite figure out whose burden it is to change this. Is this something that we as a sector need to think about more deeply, and folks like you need to be publishing your failures? I have a hard time saying, Jonathan, every time you mess up you should be publishing about it to your donors and your supporters and your board. And at the same time, on the flip side, you’re learning a lot through failures at times. We all fail. None of us are perfect. And that learning, the insights from that, maybe you don’t even fully learn from it because you don’t want to admit the failure. The move is to paper over it, to reframe it, to spruce it up for the impact report and the annual report and your funder reports, so that it looks like you’re doing a good job. And you are doing a good job, there’s a lot of success too. So what does that bring to mind for you?

Jonathan Hicken [00:14:20]: There are a few things. First is the scale of failure. It’s true, I am willing to talk about failures at a project level or an operational level, these smaller, lower-stakes things where, honestly, it’s okay if I name the failure here, because the impact is still happening, or I’m still confident we’re delivering on our promise big picture, even if this one little piece didn’t work. So there’s an element of scale: at what point is it no longer safe to talk about failure? And I certainly suffer from this. I’m motivated to tell the absolute best story about the work we’re doing.

In fact, I think you and I are a little bit guilty here. We’re teaching people how to talk about this stuff in a really compelling way, which is a superpower, especially if you need to obscure failure. We can tell a great story.

Eric Ressler [00:15:30]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

So this brings to mind something for me: I don’t think we should expect folks like you to publish every failure they have. But maybe one step we can commit to is being honest internally with our teams, like, “Hey, this was our hypothesis. We tested it. Here are the results, and here’s where it worked and here’s where it didn’t.” Or, “Hey, this thing didn’t work.” And we’ve got to be real about that and avoid the common gravity toward reframing it as a good learning or a win in a way that diminishes the true insight we can get from admitting it didn’t work.

I’ve experienced this. We do retrospectives on every project, and there are times where I can feel our project team, out of respect and deep care for one another, not want to bring up parts of the project that failed, or risk throwing people under the bus. But then there are times where I’m like, this isn’t a real retrospective if we aren’t willing to have those tough conversations, and even, this is delicate, call out respectfully where either individuals or parts of the process didn’t work. Because if we can’t even do that, then why are we doing a retrospective? And that’s just one example. I’ve felt the same way about new ideas and initiatives. I have ideas right now that I’m really excited about that are probably really dumb, that in six months I’m going to be like, what was I thinking?

Jonathan Hicken [00:17:55]: Building the habit and building the comfort with discussing failure is certainly part of it. Although when you bring up that example, okay, we can build this shared comfort with it, but if it’s just within the team, what is that really doing for the sector? So where my mind goes is, maybe we just hatched another conference idea. What are the forums for discussing this failure in a safe place? How do we mitigate the risks that exist to discussing failure? And the risks are primarily social capital and funding. So what’s an environment where you can remove those risks, where the social capital and the funding are not on the line, but we can still have that collective learning and collective growth? A closed-door conference where funders are not invited, which is the opposite of what we usually do, where we can really be real about this stuff.

Eric Ressler [00:18:55]: And my sense is that there are things like that going on at some level. There’s not the de facto one, though. I couldn’t name that conference right now.

Jonathan Hicken [00:19:05]: The social impact failure conference.

Eric Ressler [00:19:05]: Could we all go dressed up in costume and anonymized or something?

Jonathan Hicken [00:19:10]: TM, TM, TM.

Eric Ressler [00:19:10]: I like that idea a lot, man, because it reminded me of this Silicon Valley site where you used to be able to talk about your employer anonymously.

Jonathan Hicken [00:19:25]: Oh, Glassdoor?

Eric Ressler [00:19:25]: No, there was another one specific to the startup world. It’s kind of like that, because there’s that fear of not being hireable. You don’t want to go talk about the company you’re just at, but it was this sector-wide thing for the startup community: “Hey, who to watch out for,” or “here’s what it’s like to work there.” Glassdoor is a similar thing. I don’t know if that’s quite the right flavor of it, but I like the idea of giving us permission as a sector to redefine what failure means and to embrace it to a degree. It’s a big ask to say start publishing all your failures, and I don’t even know if that’s the right move right away. But what do you think about the idea of starting internally? I know that’s something you do at some level.

Jonathan Hicken [00:20:15]: Failure is something we discuss regularly on my team. Failure is encouraged, because we need to be able to take risks as we try this ambitious new vision, and we know some things are going to work and some aren’t. We accept that as truth going into the work. And so if we accept it going in, then there’s no shame in naming it when it happens, because it’s there.

Now, there are certain things we can accept failure in and certain things we can’t. Part of my job as executive director is to draw those lines for the team: here’s where we can fail, here’s where we can’t. A really simple example would be, we’re going to try this new event and a new format, and maybe we’ll learn that it totally flopped and we’re never going to do that again. And you know what, that’s fine. No one is ever going to hold us to account on an event that sucked. But we cannot miss our revenue and expense numbers, because then the stakes are too high. That’s a simple example of knowing where failure is acceptable.

So I do think that’s a muscle we all need to have, and maybe one that doesn’t exist pervasively. It’s fundamental to how I work. I’ve never worked on a team that didn’t have that, because I need to work in places that embrace that. But the question becomes, how does that spread? How does that discussion of failure cross organizations?

Eric Ressler [00:21:55]: I’m reflecting on a couple of things. One, we just did an episode about how to design your organizational culture. And to me this is a big part of that culture building. It’s building in a standard and a guardrail around what you can fail on, and encouraging people to rethink failure. Because a lot of people in our space have been deeply trained that failure equals bad. I think that’s a deep, almost subconscious belief in the sector.

Jonathan Hicken [00:22:25]: I’d say that’s not even the sector, man. That’s societal. Most of us grow up believing that getting a C on an assignment is failure, and that’s bad.

Eric Ressler [00:22:35]: Yeah, these are deeply held, deeply rooted beliefs from school age. Watching our kids get into grade school and seeing homework and grades starting to come in, it’s like, oh, here we go, it begins, the standards, the structure. So I agree it’s not just the sector. But I do think there’s something distinct about this sector that makes failure even worse. And I think it’s because when you think about failure to the mission, the stakes can literally be deadly for the people we’re trying to help at times. And if not deadly, you’re putting donor dollars on the line in a way that, hey, if a startup throws away a million dollars from VC funding, we just cough at it, like, yep, cost of doing business. But in our space, a million-dollar grant from a major foundation wasted is somehow much worse. Even that, I’m starting to think, why is that the norm?

Jonathan Hicken [00:23:30]: Let’s imagine a sector where failure was embraced and celebrated. What would that world look like, and how would it be different from today?

Eric Ressler [00:23:40]: This is part of why I’m kicking this around. I think it’s the third time I’ve introduced this topic loosely and then said, all right, we’re just going to do the episode. Because I believe it would be a much better, more effective, more joyful sector to be part of.

Jonathan Hicken [00:23:55]: I think we’d also deliver better results. Because if we’re all stumbling over the same problems, and obviously in social impact there are a million variables that could change someone’s circumstance, but just to use housing as an example: if one housing group fails and that lesson can be shared across to other housing groups, that’s collective learning that maybe isn’t happening right now. And maybe we actually start to see an acceleration of social impact results.

Eric Ressler [00:24:25]: Yeah, I think we would. And again, I don’t want to paint this as no one is doing this, but there’s lots of room for us to take it to the next level as a sector. Can we talk about design thinking a little bit too? Because we’ve gone into the scientific method and this failure thread, which is probably, in my opinion, the crux of why the scientific method is not being applied properly in our space. Similarly, on the design thinking side, design thinking is an incredible framework that can be applied. Does it have shortcomings? Is it the absolute perfect solution for all problems? No. But it’s gotten some flack and pushback in the space as of late, and I’m here to defend it a little bit.

What I want to say about design thinking is that it’s built specifically for these types of problems, the ones described as wicked or intractable, that don’t have clear solutions, where you have to embrace, hey, it’s going to be a little messy. And that’s what I like about this approach: as much as we want to be evidence-based, and this is where we start to diverge a little from the scientific method, it’s going to be messy, it’s going to be imperfect. Design thinking embraces that, but most importantly it gets you out of the overthinking, over-intellectualizing, over-planning mode that I find our sector falling into far too often. I see this through orgs where we have the three-to-five-year strategic plan that’s perfectly, neatly laid out. And I’m not here to totally bash strategic planners, I know that seems to be the thing we do on the show a lot, but what I am here to challenge is, that’s not how the world works, man. It just isn’t. I’m not saying you shouldn’t plan long term, but I’d like to see orgs take a lot of that time they’re putting into planning and run experiments and prototypes and get them in front of the people they’re actually trying to help and serve. That’s what design thinking is built to do. So I’d encourage anyone in the social impact space, there are great resources online. IDEO University runs courses, the Stanford d.school runs courses that are pretty reasonably affordable. You can do them remotely or in person. I’d just like to encourage the sector to dig into this a little bit more.

Jonathan Hicken [00:27:00]: There’s a clarification worth making here, which is that experiments and prototyping can happen on different timescales. And that’s really important, because there might be someone listening thinking, “I can’t do a two-week experiment when I’m dealing with social services.” And I’d say, fair enough. Your experiment could look like a three-year pilot, where you have enough runway to educate your beneficiaries on how this is going to work for a little while and test something out. So I just want to name that the implementation of some of these ideas can happen on different timescales. What matters is that you’re going in comfortable with the fact that this might not work, and that you’re prepared to learn and share what comes out of it.

Eric Ressler [00:27:45]: And design thinking, the other element that’s especially appropriate for our sector, is that it embraces and expects iteration. You’re expecting the prototype to fail, and the whole purpose is to learn from those failures and come up with a new version and do it again. You repeat that process until you have something worth shipping, and that’s even a bit of a judgment call at that point.

Jonathan Hicken [00:28:10]: Something worth noting in design thinking, and in the scientific process a little bit, is that the process is in service of a very clear result, a very clear endgame. In the sector we can get distracted, and this might not even be the sector, this could just be business in general, but we can get distracted by inputs. Maybe it’s what serves the staff best, maybe it’s what serves donors best, maybe we think it optically looks best. There are all these variables that could derail an experiment or have us iterating toward outcomes that matter less than the impact outcome.

Eric Ressler [00:29:00]: Yes. I think you have to take all of those into account, and that’s where discernment comes in, and where leadership comes in to a degree. To take it back to your example, to make this not feel like such a big academic thing for people to take on: recently we’ve been making some project management changes at Cosmic, like how and where we communicate, in an effort to reduce the number of channels we have to check every day. Simple thing. I want to shout out Karen on my team, because I had some ideas, we had some ideas, Karen and I, and she took it upon herself to go interview everyone on the team and hear from their point of view where things were falling apart, and basically challenged a lot of assumptions that Karen and I had made around where things were hard.

And what we learned is that a lot of the pain points Karen and I had were completely irrelevant to the rest of the team members, partially because of our roles. Nonetheless, we’re making some changes, but that’s a very simple version of design thinking. First of all, she had enough empathy to go ask the people who were going to be affected by this. She listened. Right now we’re in the prototyping process, we’re rolling out some changes. And what we said to the team is, hey, this is an experiment, it might fail, and if it fails, that’s okay. I even said today, we can control-Z this thing. And then Lisa on my team was like, well, we’re probably not going to control-Z it, but we’re going to iterate. So is this the absolute perfect textbook version of design thinking? No, but we’re taking the parts that matter. And in this case the parts that matter are: are we engaging the people who are actually affected by this problem and the proposed solutions? Do we have empathy for them? Are we listening to them? Are we building out prototypes and experiments, and are we willing to fail and iterate from that? So it can be something as small as that. It doesn’t have to be your entire focus toward impact.

Jonathan Hicken [00:30:50]: And there’s a lesson in that if we extrapolate that example toward a really big, hairy social impact problem. Let’s say hunger, for example, and food banks, and how are we getting food to people who need food? There could be experiments in terms of, we still need to get food to the right people, but the way we do that, this part of the process or that part, could we get more throughput? There are things you can tweak and improve on that don’t risk the results of getting people food who need it. And I think that’s the crux there of knowing where failure is okay and where it’s not. We can’t fail at getting that person the food. We can fail at this particular piece of the process, which we know we can roll back. We can reverse that. That’s something that for you is like, we can’t stop delivering great quality product to our clients, but we can tweak this piece and we’re okay with it failing. And that’s that discernment that I think maybe could be cultivated more broadly.

Eric Ressler [00:32:00]: Yeah. And the questions to ask are: what are the stakes of failure for this given experiment? Who carries the burden of those mistakes if they fail? Are we asking the beneficiaries, the people who need food? If we fail, they’re not going to get food. Well, first of all, the stakes are too high, and the risk is going toward the wrong people. Now, I’m not saying you should never experiment on things that might be high stakes, but you have to be really cognizant of that.

Jonathan Hicken [00:32:25]: All right. Well, look: scientific method, failure, design thinking, I think there’s something here. At minimum, we came up with a new conference idea, social impact FailCon 2027.

Eric Ressler [00:32:40]: Get your costumes and masks ready, folks.

Jonathan Hicken [00:32:40]: Thanks for bringing the topic.

Eric Ressler [00:32:40]: Yeah, thanks for riffing out with me, Jonathan. If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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Philanthropy takes a lot of heat for being slow to move money. And the thing that’s usually blamed for that is learning, all of the evaluating and the reports and the pontificating. Our guest today thinks that this critique is fair, but that the blame on learning is actually not accurate.

Katherine Haugh is the founder of the Convive Collective, a learning partner to some of the largest climate focused philanthropies in the US and Europe. Convive has co-created a learning philanthropy framework with an initial cohort of six funders, including Co-Impact, the Rockefeller Foundation, and the Lodz Foundation.

In this conversation, we cover what’s actually slowing philanthropies down if it isn’t learning, why learning is often used as a way to dodge a decision, how trust-based philanthropy and rigorous learning can actually reinforce one another, and the two things a philanthropy needs in place in order to become an effective learning-based philanthropy or organization.

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Episode Highlights:

[00:01:20] What a “learning organization” actually means, and why the for-profit version doesn’t fit philanthropy
[00:02:30] Three reasons the corporate learning playbook breaks down for philanthropies
[00:08:30] The false tension between trust-based and learning-oriented philanthropy
[00:10:20] The power dynamics that push grantees to hide what they’ve learned
[00:14:15] The real reason money moves slowly: control and ego, not learning
[00:18:00] Why learning has such a good brand, and how that hides dysfunction
[00:19:45] Learning as a way to dodge a hard decision
[00:20:45] What authentic, effective learning actually looks like
[00:26:30] The two non-negotiables: leadership commitment and psychological safety
[00:32:35] Why philanthropies won’t publish their failures
[00:37:50] What the pilot cohort did that no one expected
[00:44:30] The “healthy life” metaphor for becoming a learning organization

Notable Quotes:

[00:15:50]: “I actually think that the reason why that is is a function of control and ego.” Katherine Haugh

[00:17:40]: “The message from a lot of these foundations is, ‘We need to be responsible stewards. We need to learn, we need to evaluate.’ But that’s not actually the part that’s slowing them down.” Eric Ressler

[00:18:00]: “Learning has a great reputation. Learning is a great brand. No one ever says, ‘We hate learning.’” Katherine Haugh

[00:19:45]: “The safest action that saves face within a foundation is, ‘That’s a good point. Why don’t we learn more about this?’ And it can punt an uncomfortable decision in a seemingly professional way.” Katherine Haugh

[00:26:45]: “The best thing that’s going to happen from taking this risk is not the outcome, it’s the learning.” Katherine Haugh

[00:28:15]: “You can have excellent evidence, you can have the best sense-making process, but if your team doesn’t feel safe to say what they really feel, it’s all for nothing.” Katherine Haugh

Resources & Links:

• The Convive Collective — Katherine Haugh’s learning and strategy partner to climate-focused philanthropies

• The Learning Philanthropy Framework - helps climate-focused philanthropies see what good looks like, measure progress, and strengthen the learning practices that power impact.

• Center for Evaluation Innovation — cited at [00:16:30] as the source tracking how much of philanthropy portfolios go to learning and evaluation.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:00]: Katherine Haugh, thank you so much for joining me today.

Katherine Haugh [00:01:05]: Thank you for having me, Eric. I’m so excited to be here.

Eric Ressler [00:01:15]: So I would love to dive in and just start to understand this idea of a learning organization and more specifically a learning philanthropy. Tell me a little bit around what does that actually mean? What does learning mean in the context of philanthropy?

Katherine Haugh [00:01:20]: Oh, fantastic question. So excited to speak about this. So a learning organization is actually a term that was coined in the late ‘70s by researchers who were trying to understand why certain for-profit companies outperformed their peers. And they came up with this theory and this concept that organizations that really put learning at the heart of their operations and culture are able to adapt faster, learn from feedback faster, innovate more, and ultimately create more staff satisfaction within their company cultures so they have higher retention as well. So this concept kind of took root in the study of for-profit companies, which is great, but it presents a challenge for us in the philanthropic sector because we hear all the time that foundations say we want to be a learning organization because that’s ultimately a way of being more effective. But that term and the literature associated with it is still very much rooted in mental models and incentive structures for for-profit companies.

And we see three key differences for philanthropies. First and foremost, a lot of the literature is around how to use information to beat out your competition. So don’t share data, don’t share anything, pointy elbows and beat out the next guy to be the best in the market. That doesn’t quite work for foundations or in the philanthropy sector in general. If you’re trying to achieve any kind of lasting change, you need to do that in collaboration and coordination with others. You actually have a higher incentive to share information than to keep it for yourself. The second one is this concept of efficiency. So a lot of the literature for learning organizations is around how to gather information so you can be more efficient. Think Toyota, think Microsoft Hackathons. It’s thinking how can we get as much information as possible so that we can cut out steps in the process, be more efficient to ultimately making profit?

That’s also problematic for us in the philanthropic sector because sometimes in order to be more effective, we actually have to be less efficient. We have to pause, check our assumptions, gather more information before we’re ready, see what happens in terms of making different hypotheses and different bets. And so a focus too much on efficiency actually hurts us and makes us less effective overall. And the last piece of the puzzle is around feedback. So you’re going to love this one because for for-profit companies, feedback is built into the business model. They’re wondering, do consumers like this or not? You need to be constantly paying attention to signals of success. Whereas with foundations in particular, that feedback isn’t automatic. It needs to be intentionally structured and built in. It’s totally possible for a philanthropy to be running a strategy and a way of grant making that’s absolutely not working, but without intentionally collecting data and feedback about their strategy, they could not know and be running an ineffective operation.

So that’s why also for us, last but not least, partners who are most close to the work need to feel safe to actually be able to tell their foundation partners this is or isn’t working without fear of retribution. And so there’s a whole other element of the relational side of collecting data and feedback and to have that be truly for the purposes of learning and not for accountability and then there be grant making repercussions.

Eric Ressler [00:05:45]: So in your experience working with a number of these philanthropies, and you all have worked with a lot of the major philanthropies in Europe and the US and all over, how are philanthropies specifically? And when we say that, I think just to be clear, we’re also talking more specifically about major institutional foundations largely, but also maybe family offices who act more institutional. What are they doing right now for learning? What was the need that you saw working with these folks?

Katherine Haugh [00:06:05]: Yeah, totally. And we like to use the term philanthropy because it’s broader really because the word, what that means is the love of humankind. So it captures the essence of what this sector is about from huge institutions to tiny family offices to individual donors and their partners. So that’s an intentional choice on our behalf in terms of language. But what we see is that I would say maybe the focus primarily for foundations when it comes to learning has traditionally been evaluation. So thinking, let’s evaluate how effective our work is. So either I think more traditionally that’s done with grantee partners. So saying, “Hey, we’re giving you this grant. We’d also like you to evaluate it when the grant is over and share with us how effective it was. Did you reach your goals? Did you hit those outcome targets and why or why not?”

I think since that’s maybe decades old practice that has evolved through much research, a lot of iteration to become more developmental and emergent. So instead of the end of a grant partnership saying, “Hey, what did we learn? What did we achieve?” It’s more throughout the process that you’re reflecting with your partner like, “Okay, are we on track? Are we not on track?” And I think even more now with the onset of trust-based philanthropy, that’s been less about being really controlling about reporting and setting the direction of what success looks like and allowing the folks who are closest to the problem to set the direction and determine what success looks like and course correct as needed. So I think now we’re coming into a moment where the concept of a learning philanthropy is really vital, mostly because now we’re at a place where folks are recognizing evaluation isn’t quite enough.

That’s just one way to learn. And somehow that has become synonymous for learning like, oh, if we evaluate our grants, then we’ll have learned. But we know from the study of how adults actually learn that passively engaging with material like that is one of the least effective ways to learn. And it really needs to be a constant practice and a way of working and thinking that’s embedded to how a foundation works with its partners and each other. And interestingly, Eric, the trust-based philanthropy movement has kind of created this tension that we don’t feel is there between being trust-based and being learning-oriented. It’s almost as if folks sometimes conflate that if you’re trust-based, that means you’re not asking your partner for any data or information, you’re not reflecting and adapting with them. But we think actually they go hand in hand, but it’s about the orientation. It’s not saying, okay, give us this data because we’re checking to make sure that you’re doing things correctly. It’s like, let’s share information both ways so that you can be set up for success in your role in the ecosystem, and same from the foundation’s perspective in terms of the decisions that they need to make.

Eric Ressler [00:09:20]: Yeah, there’s so many good threads to pull in there. So first of all, I think to your point, I’ve always heard this kind of lumped together with MEL, measurement, evaluation and learning.

Katherine Haugh [00:09:35]: Exactly.

Eric Ressler [00:09:40]: And learning feels kind of like this tacked-on thing, right?

Katherine Haugh [00:09:42]: Yes.

Eric Ressler [00:09:45]: And what I think I’m hearing you say is that none of those things work in a silo. They all need to work together. And I’m also really interested to dig a little bit more into this tension between, or maybe even this misunderstanding of what trust-based philanthropy means, where if you interpret it incorrectly, it’s that there is no evaluation whatsoever in trust-based philanthropy.

Katherine Haugh [00:10:05]: Exactly.

Eric Ressler [00:10:05]: It’s a fully trusted hand over the money and hands-off and hope for the best, which I don’t think is what trust-based philanthropy was even initially set out for.

Katherine Haugh [00:10:15]: Absolutely not.

Eric Ressler [00:10:20]: So I’d love to hear, there is, I think in the worst case in a philanthropic relationship, power dynamics that actually run very counter to learning, right? Where a grantee feels the need to perform, to produce results, sometimes even to flub those results or to massage the statistics to look like things were effective even if they did have learnings and they’re scared to share those learnings for fear of not getting a grant again from the same funder.

Katherine Haugh [00:10:45]: Exactly. Exactly.

Eric Ressler [00:10:50]: And I think this is largely where the movement, I’ll say, around trust-based philanthropy came from, is just an objective measure of like, “Hey, this is not a healthy way to do this work.” So I’d love for you to paint a picture of the counter narrative to that. What does this look like at its best and how does learning fit into that?

Katherine Haugh [00:11:05]: Yeah, that’s an amazing question. I think first and foremost, what this looks like at its best is that decision-making authority about what the activities in the grant should be focusing on and what the goals are actually sit with those who are closest to the work or the problems that they’re trying to solve. I think a lot of challenges come from still this top-down orientation around foundations setting strategies, setting the directives, saying these are the challenges we see, and this is how we believe change is going to happen with a theory of change if then. And then it’s almost like finding grant partners who fit into that vision already creates so many problematic relational elements and also ultimately makes a foundation, in my view, significantly less effective with that way of orienting to a grant-making relationship. So I think it actually starts with working with folks who are closest to the problem that you’re trying to address and putting learning first and foremost.

I think a lot of times foundations will come in or start with a new strategy. And because there’s so much pressure to get money out the door, get moving, quickly show results, keep board members happy, keep fundraising going up, there’s not often enough time for really properly understanding the root causes of a problem and thinking through who are the right actors to support you in moving the needle because there’s so much time pressure around, okay, we have limited trust perhaps from above. We have to quickly demonstrate that we’re making progress. Otherwise, this whole thing might come crashing down like a house of cards. So I think actually a lot of the tendencies that we see in philanthropy can be traced back to leadership, to board dynamics, and then we see them play out either positively for learning and in a trust-based fashion or negatively where things are becoming really inefficient and performative and hollow.

I think a lot of grant partners struggled not only just to be honest with their grant managers to say, “Hey, we’re actually not on target for this outcome, and here’s what we’re learning, and here’s how we’re going to pivot.” But I also think that foundations currently don’t often have the capacity and resources even to work with the data they receive from partners. So grant partners have to fill out every different type of reporting form because there are many different funders. And in my experience, most foundations have not adequately found a way to truly learn from that material that they receive from their partners. So I think folks are reticent to really feel that it’s truly a learning exercise because it’s not quite clear how that feedback loop gets closed.

Eric Ressler [00:14:15]: So I want to make a counter argument to hear how you think about this with regards to learning. One of the criticisms that I hear about philanthropy in general, and especially major philanthropy, is that we actually spend way too much time as a sector thinking, learning, evaluating, measuring, writing reports, and not enough time and effort actually just doing and getting money out the door. You hear a lot of criticism. And I think some of this is valid around major philanthropies not spending down fast enough, not hitting more than their minimum 5% payout, which includes overhead on their side. It doesn’t even go directly to grantees. And so how do we incorporate learning as a way to get more money out more effectively in the sector?

Katherine Haugh [00:15:15]: Yes, I love that. I think this is an amazing question and also I think represents the tension we were speaking about between being trust-based and being learning-oriented and why those two sit together in a complimentary way. I agree with you that I think the critique around philanthropy being too navel-gazing and slow to move money is valid. And I do see a lot of inefficiencies that are created within foundations around unnecessary bureaucracies that actually slow them down from just giving as much of their portfolio away as quickly as possible. So I totally agree with that. I actually think that the reason why that is is a function of control and ego. Because there’s a lot that goes on within foundations from my viewpoint around creating many unnecessary steps to keep folks within the foundation clued in, feeling important, adding advice, adding perspectives when all of that could be shortened significantly. But if folks were more comfortable to take risks and had less control and ego in the game, and I think that that is very much informed by the type of founders who create the foundation and what their ethos and philosophy is around why they’re doing philanthropy. And so I think that in my view, that has very little to do with learning because actually most foundations spend less than, I have to look up the stats, so I’ll check myself, but less than 1%, maybe 2% of their entire grant-making portfolio on learning evaluation impact measurement. And this is something that’s been studied by the Center for Evaluation Innovation year on year to see if that percentage is picking up and how foundations are spending their funds internally or supporting their partners to learn.

And it has bumped up and bumped down, but for the most part stayed abysmally low. So I hate that learning gets thrown in with maybe just a control related bureaucracy and friction that’s happening within foundations that then becomes part of that navel gazing critique.

Eric Ressler [00:17:30]: Yeah. So your take on this is that the reason that’s slow is because of learning is actually not accurate and a charitable interpretation, and it’s actually more about bureaucracy, ego.

Katherine Haugh [00:17:40]: Definitely.

Eric Ressler [00:17:40]: The message from a lot of these foundations is like, “Oh, we need to be responsible stewards. We need to learn, we need to evaluate.” But that’s not actually the part that’s A, slowing them down, or B, even accurate for the most part.

Katherine Haugh [00:18:00]: Definitely not. I think also, we talk about this a lot on my team, that learning has a great reputation. Learning is a great brand. No one ever says, “We hate learning,” or, “We don’t really do much of that here.” Everyone is like, “We’re learning.” But somehow I think learning can be a catchall for covering up. Actually, we’re just deliberating internally and we can’t make up our minds, or actually we’re dealing with some dysfunction or we’re just getting started and we’re figuring out our operations or we’re dealing with disagreements between our leadership and our board. That could all be under the umbrella of we were learning, we commissioned a report, and I think also a bit of ego in learning and a bit of reinventing the wheel. There’s so much in philanthropy where there’s this idea of we’re a foundation, we’re going to do something totally different. We’re totally different. And this special snowflake phenomenon that we see a lot where foundations significantly under leverage publicly available data, information, reports, but there is some feeling about like, oh, okay, well the natural next step is always to learn something a bit more. But in our view, that’s like, okay, let’s commission a study to gather some research, but doesn’t actually change behavior. And I think too, something that I see all the time is that when there’s actually a decision to be made that might alter someone’s thinking, might challenge somebody’s position, might actually admit, okay, we messed up here or we want to do something different, the safest action to take that saves face within a foundation is, okay, well, that’s a good point. That’s interesting. Why don’t we learn more about this? And it can actually punt an uncomfortable conversation or an uncomfortable turning point for the foundation or a critical juncture down the road in a seemingly professional way. So learning gets a bad rep, I think, and a good rep at the same time.

Eric Ressler [00:20:25]: Learning is like the cover.

Katherine Haugh [00:20:30]: It’s a cover. It’s a good cover, man.

Eric Ressler [00:20:35]: Yeah, right. Okay. So we just spent a little bit of time talking about all of the fake learning and what that might look like. So tell us now, what does authentic, real, constructive, effective learning look like instead?

Katherine Haugh [00:20:45]: That’s a great question. My mind goes to, it really starts at the very beginning with first and foremost, how the foundation is formed. So something that we’re researching right now as part of the learning philanthropy project is we’re talking to learning leaders across very different foundations and we’re asking them, tell us the story of how learning became a focus for this foundation. How did you embed it culturally, operationally? What value is it bringing to you? And one thing that’s emerging from these conversations is the way that learning was initially conceived by the leader of the foundation sets the tone and level of ambition that learning can really take within that organization. So where I see it working the best is when a CEO or an executive director comes in to start a foundation or even take over an existing foundation, and they themselves as an individual have a very strong learning orientation.

So what that looks like is that they’re typically very humble. They like to be challenged. They like when people tell them disconfirming evidence or have dissenting opinions. They look forward to that. They’re very proactive with feedback. They’re good listeners. They’re comfortable to make mistakes where they’re like, “Yeah, no, we’re going to take risks. I made a mistake.” And they say things like, “I used to think blah, blah, blah. Now I think blah, blah, blah.” Or they make their thinking visible by saying, “The following experience led me to believe this, this, and this.” And it’s interesting when a leader has that kind of orientation, the amount of influence that they carry culturally and operationally is significant. I’ve learned about learning leaders. That’s a well-studied topic of how influential they were. And I thought, surely it can’t be that simple. There’s so many other pieces, structure, resources, learning champions, psychological safety, but it really by and large is the most important indicator of how much that organization is truly going to value learning. For example, if you have a foundation leader who says, “Yeah, we value learning,” but it’s tokenistic, they don’t really set aside staff time for it, they don’t put any resources behind it, all of the things that I said actually model learning, that’s how you’ll see for the most part folks across the foundation modeling that same behavior where they’ll say, “Yes, we value learning, but no time is set aside for it. Folks are not diving into reports, reflecting on their behavior.” And my view is that that trickles down to the relationship that they have also with their partners where it becomes still tokenistic there. So if I was a partner to that foundation, I would be reading between the lines like, oh, okay, they say they value learning, but it’s really more performative and tokenistic expressed than truly embodied and lived. So I’m not going to spend as much time reflecting and adapting necessarily in this partnership because it’s just not as important as some other things.

Eric Ressler [00:24:15]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

What I’m reflecting on and hearing all of that is that it sounds like both internally and in a partnership-based way, it requires permission. And you use the term psychological safety and trust comes back to me again. Because if an individual program officer or staff member within a philanthropy doesn’t feel like they can fail, and maybe we should talk a little bit about failure and risk-taking because I think they’re basically inseparable from learning.

Katherine Haugh [00:25:25]: Totally.

Eric Ressler [00:25:25]: Then they’ll never learn. Because you mostly learn not by being successful, but by failing and iterating in my opinion. And I’d love to hear your take on whether or not that fits into your framework. But that’s what I see is when you get into these rigid like, “Well, we’ve always done it this way, this is the proven way, this is best practice. These are the metrics we’re going for,” you’re predetermining the results at that point instead of being open to almost really a more scientific approach to this where you generate a hypothesis, you run iterations or tests or prototypes, you measure, you evaluate, you learn. In the best case, that’s I think what we’re pointing to. But if there’s not the ability to fail in the same way that experiments in the scientific world are set up to fail, then the learning never actually happens and it just becomes performative.

Katherine Haugh [00:26:30]: Exactly. Wow, you’ve said it in such a beautiful way. I will say learning is so scientific the way that we’re talking about it. Our clients love to use the language of hypotheses and we’re testing this, we’re experimenting here, we’re taking a risk. And we’ve started to call it intelligent risk, like taking intelligent risks because we have some information, but we’re going out on a limb. And actually the best thing that’s going to happen from taking this risk is not the outcome, it’s the learning. So we really have to pay attention to our learning. So I love how you framed it like that. That’s really exactly spot on. And I will say there’s two areas of our framework that we’re starting to see are evergreen, which is if you don’t have these two pieces, it’s not really useful to start building in other areas because it’s not supported. It’s like a foundation that could collapse. And those two areas are leadership commitment to learning, that it needs to be there from your leadership, that they care about learning. It’s a value, it’s an identity. We are a learning organization, we’re a learning philanthropy that needs to be there, not just spoken, but in practice.

And second, that there’s a certain level of psychological safety across the foundation, any organization, any team, because it’s just unequivocally true. If people feel stressed or unsafe, unsafe to be themselves, to offer a dissenting opinion, to fail or make mistakes in front of each other, they’re going to be significantly less effective in their roles and almost never take risks. And then not really learning, following what’s the safest thing that I can do to keep my job here or keep my social status. Those are two different elements of risk where people don’t want to feel outed or ousted for who they are. So I’m glad that you brought that up because that for us is like you will hit a concrete ceiling with everything else that you tried to do. You can have excellent evidence, you can have the best sense-making process, but if your team doesn’t feel safe to say what they really feel, it’s all for nothing. So we really love focusing on that. That really is the foundation of a learning philanthropy.

Eric Ressler [00:28:45]: So we’ve been talking about this in the context of funders mostly, but I’m also curious because a lot of the listeners of our show are recipients of funds, they’re executive directors or staff at nonprofits and social enterprises as well. And I’m curious, how does this framework or does this framework translate to practitioner organizations as well, or is it really more focused on funders?

Katherine Haugh [00:29:15]: I will say the framework is really focused on funders for the reason of really wanting to change funder behavior as it relates to learning. When we first started on this endeavor, we were like, “Surely something like this exists.” We hear foundations say, “We want to be a learning organization all the time,” but then they kind of secretly whisper after that, “But what does that actually mean and what does it look like in practice?” And so oftentimes they’re copying and pasting from each other, “Oh, this foundation did this learning agenda or this foundation did this evidence tour.” But we are seeing that that copy and paste method doesn’t quite work because it’s not really using the principles and understanding of what a total learning philanthropy looks like and adjusting that to your context, your goals, your learners, all of that. So our hope is that by building this framework and maturity tool and starting conversations around it, that this will create a place where foundations can look to for inspiration, for practices of excellence, for guidance that ultimately help foundations up-level their learning work, which ultimately would help their grant partners actually be in authentic learning partnerships with them.

So we were thinking a lot about that, if we should have two different frameworks or how to bring the pieces together. And to make my own thinking visible, that’s what we’re imagining is that’s kind of our theory of change that it’s our hypothesis that we will be collecting our own data on and experimenting with. And in our framework, we have a whole component on learning with partners. So this is an area actually where it kind of flips the relationship on its head in a really nice way because right now, typically most foundations collect information, data, even sometimes feedback from their partners about how’s it going in this partnership or tell us what you’re working on and what you’re achieving. It’s very rare that foundations are actually inviting their partners into a co-creative learning process around that information. It’s kind of like, “Hey, submit your stuff. We will learn from it and then sometimes but rarely share back what we’ve learned.” And so our orientation is if you are truly a learning philanthropy, you are gathering information, you’re also sharing information with your partners, but that learning experience is co-created and of an equal footing. And so I hope that this tool will also give the opportunity for partners to rate their philanthropic partners on what’s the level of maturity that they experience. Because for our foundations who have chosen that component to say, “Hey, we want to self-assess,” that requires that their grant partners are part of that process. And it’s hopefully creating a new way to say, “Yeah, actually I would put us in our partnership at a two out of five.” And it’s not so much calling out the foundation, it’s more about how strong is our learning partnership between us and how could it be stronger so that we could be more effective together as a pair, as a duo? So I’m really excited about that element of it.

Eric Ressler [00:32:35]: Yeah. And to compare again to the scientific world where so much about doing science is publishing. I mean, actually even maybe to a fault where publishing becomes the metric of success. But what I’ve reflected on over the years in this space is we hear a lot about, especially philanthropies learning, but then there’s very little publishing from philanthropies around what actually worked, what didn’t, what’s the hypothesis around why? And I think again, it comes back to this idea of being willing to fail in public. I think one of the things that works so well about the scientific world is that failure is not failure when it comes to science. Failure is learning. And I think that’s the ethos that our sector is moving towards and needs to embrace. But it’s going to require all parties to come together and say trying and failing is okay. I think the reason that that is hard to do is because sometimes in this space, failing means real negative impacts on humans. And the same is true for science when it comes to public health, certainly. So I wonder, is my hypothesis there right around why this doesn’t happen? Is it really largely because it’s like a PR disaster for foundations to publish failures in their grant making?

Katherine Haugh [00:34:05]: Yeah. It’s even something I think deeper than that because not only do foundations may make big mistakes, it’s often more a series of small miscalculations. It’s not very frequent in our sector that there’s a massive one huge decision that led to catastrophe. It’s more kind of like a series of miscalculations, a series of misjudgments, tiny decisions that to be honest, I think is also hard to sometimes tell the story of when you’re the one making all of those decisions. And you’re kind of like, “This didn’t quite work, but I’m going to construct a narrative about why it didn’t work so it makes it not my fault.” So it saves us as much face as possible. And that’s what we see if we see anything at all. It’s like, okay, kind of like a very polished, sometimes difficult to understand publication that says a whole lot of nothing. And we’re like, “What progress was made? What happened here?” And I think also too, even for grant partners, they often don’t have that experience with their foundation partner even behind closed doors to say, “Okay, actually I think we made a miscalculation.” And I think that part of the problem is actually in the entire arrangement around the philanthropy making the decisions and having the strategy, because then it feels that all of the onus for the mistakes, then it becomes very quickly a blame game and it’s a very unsafe environment. Oh no, it was this partner’s fault. It was this part. Oh no, it was the foundation’s fault. And it’s like passing it around like a hot potato.

So I’m hoping, what I think is accurate about what you said, there is a massive fear of failure that permeates our entire sector, that prevents philanthropy from truly acting in a learning-oriented way. That means taking risks. That means working on things that are boring and not as promotional ready, not as easy to fundraise for. That means looking at precise measures that really measure change, not just gimmicky stats. And I think that part of what’s needed actually is foundations to have cover in order to operate in this way. And one of the things that we’re wondering about for the learning philanthropy framework, which is just one of many field-building initiatives that’s trying to change the tide, is that by creating a body of evidence around why learning is connected to philanthropic effectiveness when you work in a different way, when you take risks, when you’re comfortable with failure, you actually are more effective ultimately. That will hopefully start to change minds, change beliefs so that foundations are feeling more comfortable to adopt this ethos and this philosophy. Of course, it’s going to need more than just our one small but mighty field-building project, but I’m excited about a sea change and thinking about how philanthropy could think differently about failure and create more safety all for the purposes of ultimately having a greater impact.

Eric Ressler [00:37:35]: So you have a cohort of five or six philanthropic partners that were basically the pilot of this framework that you co-created the framework with. What did you learn in that pilot?

Katherine Haugh [00:37:50]: So I have been describing this project as a passion project gone rogue because we never really intended for it to become this field-building initiative. It was something that came up through conversations with many different learning leaders that I started to sketch out on computer paper. Actually, what do we know from the literature? What do people commonly say? What could a learning philanthropy look like? And for our team, we started looking into the literature, doing interviews, and then we came up with version one and then version two of the tool. So by the time we reached that point, we were like, okay, let’s pump the brakes before we spiral out into a land of detached academia, because it was kind of going in that direction. We didn’t want to create another framework that just was going to be like, “Oh, that’s interesting,” and then carry on.

So this is when we started having coffee chats with our clients, folks that we looked up to in the field and said, “Hey, what do you think about this? Would you be interested in taking this from version two to version three? And the way we want to do that with you is actually that you take the tool and pilot it within your organization.” And what I learned from that process was that I had severely underestimated the power of the tool. Initially, we thought that folks would use it as a self-assessment process. So they would say, okay, let’s look across. Let’s self-assess with a card game that we had developed in these two areas of practice, let’s say learning mindsets and evidence curation. But actually the piloters completely blew us away by using the tool in ways that we hadn’t anticipated. For example, one of them used it to pitch the vision for what organizational learning at their foundation would look like in five years and used the different behaviors that we had outlined in the maturity tool for their OKRs. So now it’s built into their strategy, it’s built into the way that they measure their own success, which is for us felt so innovative and exciting because it’s not about outcomes necessarily out there in the world exclusively. It’s also about what type of philanthropy are we being because we know that makes us more effective overall. So we love that. We also had another two foundations who took the entire tool and baselined their entire foundation. So they said instead of focusing on one or two areas, they were like, “We want to see how we’re doing overall.” And the reason why this was so exciting for them is because they could look back on five years prior and retroactively say, “Actually, we have made so much progress. When we first started here on learning, this is the behaviors we were seeing. And now it’s been five years and we have seen change.” And why that’s so important for us, obviously we love measurements, so being able to do it about our area of work is obviously a joy and a thrill.

But it’s also really important because I think learning right now is under scrutiny within foundations. It kind of goes up and down in terms of how popular it is. And right now, a lot of foundations are downsizing their learning teams, completely shutting down their learning teams because leaders are asking actually what’s the return on investment on learning? And how do we know that we’re actually making progress? We keep learning, are we actually moving the needle? Is it helping us become more strong? Is it helping us with staff retention, motivation, our culture becoming stronger, our outcomes being more sustainable? So we were really thrilled by those interpretations. And I’ll say as we welcome in new piloters, folks are coming up with even more creative ideas that we hadn’t considered, which is for us a dream come true because that’s how you would hope something like this could be adapted and truly fit for purpose based on who needs it for different reasons.

Eric Ressler [00:42:00]: Yeah, we should touch just briefly before we wrap up on this concept of the maturity tool, because I think it maps into an idea that learning or being a learning organization or a learning philanthropy is not a binary. You’re not either a learning philanthropy or not. It is a process. It is something that you mature and grow over time. So can you just speak to that area a little bit around what that looks like? And I think the tool is really good at mapping what does it look like when you’re first getting started within any one component of becoming a learning philanthropy? And what are the goals in step one, two, three, four, five for each of those components?

Katherine Haugh [00:42:35]: Yes, absolutely. And I think to build on that, there’s no one right way to be a learning philanthropy or one path towards becoming one. So in our research, we’ve found so far eight different archetypes of learning philanthropies because we know that foundations really need to play to their strengths culturally and operationally. The same is true for learning. So some folks may be actually our learners love evidence and we’re really good with evidence curation and sense-making. Whereas another is we’re really good with learning with our partners, receiving feedback from our partners, taking action. So we kind of see that foundations have their strong zones and their areas for improvement. And our recommendation is you don’t have to be thriving across every area. You have to be the version of a learning philanthropy that’s going to help your foundation be as effective and as healthy and joyful of a place to work as possible.

So that’s something that we’re excited about. As it relates to the maturity tool, that’s I think the element that is most innovative about what we’ve designed because it takes these different components of a learning philanthropy and breaks them down into observable behaviors. So you might see as you’re starting out, you’re at a lower stage of maturity, but you want to advance and hopefully creates a language and a way to share with others like, “Oh, hey, I see you guys are really at a higher rate of maturity over here. How did you get there? And how did you move from one place to the other?” Those are the conversations we’re excited to be facilitating. And maybe just to close, definitely it’s not a binary to be a learning philanthropy. And I think the best and probably the worst part for our people is that it’s a continuous journey. You’re always becoming a learning philanthropy. It’s not like you are one or you’re not one.

And the metaphor that I like to use is leading a healthy life. There’s many different ways to have a healthy life. You have maybe nutrition, you have sleep, you have your social life, you have purpose and passion, you have movement. And you might be like, okay, actually right now movement is really important to me. I’m at a higher degree of maturity at movement and socializing. And having a picture of what success looks like for you with an overall focus on improving your health and wellbeing overall is the same for learning philanthropy. And our people tend to love that because they’re like, yes, having a healthy lifestyle is not something that you just achieve, and then you can kick back on the couch and not see friends and not eat well. You have to always keep doing it. So that’s definitely the case for our work.

Eric Ressler [00:45:30]: Yeah, I think that’s a powerful metaphor also because to me it says the goal isn’t necessarily to have equal amounts of all of those things all the time.

Katherine Haugh [00:45:40]: Exactly.

Eric Ressler [00:45:40]: It’s more seasonal. I know for me personally, as I work towards living a healthy lifestyle, sometimes movement is more my focus. Sometimes socializing is more. And overall, it just doesn’t work in a practical way to have all of those things be equal all the time consistently. That’s just not how life works. And I think that’s probably true organizationally as well.

Katherine Haugh [00:46:00]: Exactly.

Eric Ressler [00:46:00]: So Kat, this has been so awesome and informative. Thank you so much. How can people who are interested in this get more involved, learn more? Where can they find the framework? Tell us a little bit about the cool stuff we’re building together and how that’s going to benefit the sector as a field building resource.

Katherine Haugh [00:46:25]: Yes, totally. So thanks to your amazing team and our partnership, we’ve built a whole website that looks absolutely stunning, is really easy to navigate and full of great resources. So folks can go to learningphilanthropy.com. And what they’ll find there is the maturity tool card game, all about the learning philanthropy, our origin story, and case studies of how different foundations have used the tool within their organization, as well as some of the insights and patterns that we’re noticing across stories of how foundations are becoming learning philanthropies and a very fun built-in quiz if you’re curious about your learning archetype.

Eric Ressler [00:47:05]: Awesome. Thank you so much, Kat. This has been wonderful and highly recommend to our listeners to go check out the site. There’s lots of great resources there. Yeah, and I’m so glad we got a chance to talk about learning. I think it’s really important and really appreciate your time today.

Katherine Haugh [00:47:20]: Thank you so much. This was such a delight.

Eric Ressler [00:47:25]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Most people who hear the word “superpowers” brace for a motivational cliché. What Sandy Gould means by it is more specific, and more useful: the thing that makes you different is the same thing that lets you create what no one else can.

Sandy has spent 36 years studying where that difference comes from. He started recruiting in tech in 1990, interviewed thousands of people across HR and leadership roles, and eventually left a strong corporate career to work with GLAAD, where he’s spent the last two years helping accelerate acceptance and representation for LGBTQ and other underrepresented communities. Trained as both a rabbi and a psychoanalyst, he’s spent his life trying to decode why people become who they become. That work turned into a book, Interlightening: Unleashing Your Superpowers.

His core claim is that the why leads to the what and the how. Ask anyone about a defining moment in their first twenty years and they’ll find it, and that moment usually explains the mission they’ve been running ever since, no matter what job title sits on top of it.

The part that matters most for leaders is what happens when you scale that idea up. Sandy treats an organization as one big person: it has an ego, it gets insecure after a win, it freezes at the top of the mountain instead of climbing the next one. So the same rules apply: name the superpowers out loud, reframe mistakes as experiments, and say “I don’t know” when you don’t, because honesty is what earns the trust to invite people into the problem.

He and Eric get into why conformity feels safe and isn’t, why teams should see their leaders disagree, and why the savior complex every leader carries is the wrong instinct. They close on three principles Sandy uses to defuse the fights that go nowhere: aim for unity through division, replace “who’s right” with human rights, and enter every hard conversation trying to broaden your lens instead of win.

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Episode Highlights:

[00:01:30] Born sick, told he’d never recover, and the belief that rewrote his life

[00:03:00] From tech recruiting to GLAAD: a career built on unleashing people

[00:05:30] Why the “why” leads to the what and the how

[00:07:00] We’re all born broken, and why the answer is both individual and collective

[00:08:30] How one word, “should,” quietly holds people back

[00:13:00] Reframing every mistake as an experiment

[00:15:30] Your organization is just one big person

[00:16:30] Why success is the scariest moment for a team

[00:25:00] The politician’s rule for honest leadership

[00:26:30] Why your team should see you fight

[00:32:30] The savior complex every leader falls into

[00:41:00] Three principles for turning debate into something worth building

Notable Quotes:

[00:05:35]: “The first thing I learned is that the why leads to the what and the how.” Sandy Gould

[00:19:25]: “The difference engine is what drives every human, every group of people, and our life and our world. If you and I were exactly the same, this conversation would be nothing.” Sandy Gould

[00:24:15]: “’I don’t know’ is a very powerful, honest thing to say. But honesty is more important. First, establish trust, then invite them in to help you figure it out.” Sandy Gould

[00:27:00]: “If you don’t show them you fight, they just think you’re hiding something, and that lowers trust.” Sandy Gould

[00:33:00]: “No one can save anyone else. anything you do to actually save them that doesn’t put agency in their hands is not only secondary, it can become risky, because then it’s a dependency, versus self-sufficiency.” Sandy Gould

[00:41:35]: “Let’s replace who’s right with human rights, and make that our priority.” Sandy Gould

Resources & Links:

• GLAAD — the LGBTQ media advocacy organization where Sandy works to accelerate acceptance and representation

• Sandy Gould on LinkedIn — where he posts about creating, superpowers, and careers

• Sandy Gould on Instagram (@spidersandy) — his “Spider Sandy” handle

• Interlightening: Unleashing Your Superpowers (book by Sandy Gould)

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:10]: Sandy Gould, thank you so much for joining me today.

Sandy Gould [00:01:10]: It is my pleasure, Eric.

Eric Ressler [00:01:10]: I often like to just dig right in with our guests, but today I actually want you to give me an abridged version of your backstory and how you got to where you are, because I think it’s quite interesting.

Sandy Gould [00:01:25]: Thank you for saying that. Here it goes. So I was born sick. Mom got sick in pregnancy. The doctor said I’d be sick forever. My parents told me, “Don’t believe what other people tell you is true. You can do anything if you work hard enough.” I figured out as a kid, by watching people, that everyone was different, that their creativity came from their difference, which means every one of the people who’ve ever lived creates in a way that no one else who will ever live creates. So they’re exclusively unique. I fell in love with difference. I realized it was a superpower. I used that inspiration to start working really hard. By the time I was 16, I had overcome the illness, and I was all-pro football, basketball, track. I was ranked in the top fastest people in my region, won all my sprint races, and realized my parents were right.

Anything’s possible if you work really hard and you live your authentic truth and you unleash the superpowers of your difference. That became my mission in life. I went to school, trained as a rabbi and a psychoanalyst, because I wanted to decode everything for everybody, which takes a lifetime, so I’m still working on that one. But then I fell into recruiting in the tech space, and eventually HR and leadership. My mission in all my roles was very focused on working with CEOs who wanted to unleash the superpowers of all their people to change the world for the better. I had a great career doing that, with many different kinds of tech and new emerging technology organizations. Then, after my corporate career hit some really great high points, I decided it was time to find a mission that would help the world move even further in advancement of these superpowers, and of people’s right and ability to be their authentic identity.

And the universe answered by having me get a call from GLAAD. I’ve been working with them for the last two years to really help accelerate acceptance, ensure equality, drive representation and storytelling for the LGBTQ and all diverse communities, and just making sure we are helping people create and be and live the identity that they’ve always dreamed of. That’s what I do. And that’s led to a book I’m about to publish about how I discovered that superpowers were real.

Eric Ressler [00:03:35]: Great. And what’s the title of that book? It should be coming out pretty shortly after we drop this episode, so plug away, man.

Sandy Gould [00:03:45]: Thank you. It’s so fun, exciting, and weird to plug my book, but it’s called Interlightening: Unleashing Your Superpowers. It really is about, from the start of my life and fighting the illness and the power and inspiration my parents brought me, to how I figured out that I had superpowers and was able to unlock them with the help of a lot of great people and coaches, and then how I started to study it in other people. I started recruiting in 1990, so between 1990 and now, over the 36 years of my career, I’ve interviewed thousands and thousands of people, and I started really studying where the superpowers of their difference turned into their mission, and then created the superpowers to fulfill that mission and allowed them to shape the world in ways nobody else was. The more I did it, the more of their stories I understood, and I was able to analyze and really identify what it was that activated those superpowers and unleashed them, so that I could then start, hopefully, helping people do that too.

So the book is about turning that into a process, so that you can take the steering wheel of your destiny, of your mission, build those superpowers, and go change the world and have a great time doing it.

Eric Ressler [00:05:00]: So I feel like you’re in a very unique position, and have unique experience, to have developed this framework, this point of view around superpowers and how people can dig into those and translate them and focus them toward missions. I’d love to hear more about what you’ve learned in doing all those interviews, in writing this book, in working in the corporate world, and now in an impact-driven way. What are some of the big themes that you see? What gets people stuck and prevents them from taking their superpowers and activating them?

Sandy Gould [00:05:35]: Great questions. So the first thing I learned is that the why leads to the what and the how. I always want to know people’s origin stories, and when I interview, that’s what I do. I ask them to start with their origin story the way I just told you mine. Once they give me the why, you can find, in a person’s first 18 to 20 years of life, the significant single moment that defined their mission and activated their superpowers. People don’t think that moment exists. When I ask them, “Tell me about a really profound moment that shaped you,” they always end up finding it pretty quickly.

Eric Ressler [00:06:15]: Wow.

Sandy Gould [00:06:15]: Once they talk about it, and then I ask them a few questions, and then they tell me what they proceeded to go do as a result of it, the why turns into the what and the how. I would actually contend it doesn’t matter what job you give them. They will do that same mission, expressed through every one of those jobs.

Eric Ressler [00:06:30]: Interesting.

Sandy Gould [00:06:30]: That’s the first big thing I learned. The second thing I learned was that people build their superpowers off of a combination of what they know they’re good at, what their friends tell them they’re good at, and then what they find out they’re good at through work and creating. That process is really important to both frame and decode. And then the third thing is, we are all born broken. Every one of us thinks we used to be the universe and now we’re just us, and we’re all trying to reclaim the universe. There are two ways to do that: be unique and be the best, or conform and align to what everyone else is doing. So, individual or collective. The real answer is both.

We have to express and create and connect to others from who we are and what is unique about us, which everyone shares. It’s the one thing we all share. And then we do have to be collective, because it gives us meaning, and align to that collective. But you define the collectives you’re in. You define how you want to be in those collectives. We grow up thinking the way to be in the collective is to conform and be like them. That’s not the answer. The answer that actually works the best for the human, because we’re both individual and collective, is to be a part of a community because we’re different, and in our difference, let our difference be the thing that makes us part of a community. Celebrate that difference, and then celebrate the connection points too. But we discover that, and that takes life and experience.

Another big thing I learned: we’re experiential learners. Even though our brain is an idealistic machine and it wants to know all the answers immediately, we don’t know anything until we experience it, usually five, six, or seven times. Then we start to figure it out. So one of the most powerful things that I knew early, and I credit my parents, is I knew that the word “should” did not make sense.

My joke is “should” should never be used, even though I’m using it to set the rule. That’s the one time “should” works. So why is that? What’s the problem with “should”? The problem is it’s the conflict between what I just described, which is that we think we are an idealistic thought machine, a brain of ideas, but we are actually an experiential learning being. The mind wants to know everything on day one and then know it forever. Experience means we’re not going to know it until we experience it many times from many different points of view, which is why in life I think we all go through cycles and repeat them a lot. And then at some point we make them or we break them. I call it the difference between recycling and free-cycling, but that’s another topic. We’ll talk about that later. What I noted early on, and it gets to your question about what holds people back: “should” holds people back.

People think, if I’m not perfect, should I really express my unique nature, or is it safer to conform? Our human animal brain wants to avoid risk. It wants safety, and conformity feels safer. It’s actually not. It turns out differentiation is what’s better for humans, and even for animals. Those that differentiate move to the top of the pack, and it’s necessary. It’s how they evolve too. But it’s scary, and we’re very fear-controlled. Eventually we will turn that fear into inspiration to create, and being scared will be an exciting part of it. I remember, early on and throughout my career and my life, I would hear “should.” The first time I heard “should” was in high school, in gym class. I was wearing two different socks, and I was wearing shorts and a jersey. All my friends were like, “You have to wear the same socks.” I said, “Why?” And they said, “You should wear the same socks. You’re supposed to. Everyone’s supposed to do it.” I said, “It doesn’t make any sense to me. It’s gym class. The socks don’t matter. And normally I’m wearing pants, you can’t see them.”

I literally didn’t understand why that was some sort of weird imperative. But what I knew is that expressing that I was different was exciting and felt great. And I not only liked it in me, I liked it in everyone else around me. That was the beginning of me recognizing this weird social “should” that didn’t make sense, that we imposed on ourselves. And then one day I was talking to somebody, and now I’ll go forward into career, and they were telling me they had pulled off an event and it was a huge success. Then they did a second event and it wasn’t a huge success. They said it should have been as good as the first one. They said, “I know I could do better.” And I had this revelation. I said, “I want to try and divide these into two different things. Knowing you could do better, that there’s more in you, you have more superpowers and more to create, more to learn, that’s great. The reason that’s great is you’re setting this higher bar knowing you have it within you, you have faith that there’s more to you, more you can create. So ‘I can do more’ is a really good motivator. But the opposite, ‘I’m not good enough,’ is a terrible demotivator, because that form of guilt, they’re both kind of intellectual guilts, and the secondary one holds you back.”

The first one moves you forward, because it’s not “I’m not good enough,” it’s the opposite: “I am good enough, I just haven’t harnessed that yet.”

So that became a guiding principle for me, for myself and to other people. I would say to people who worked for me, “When you experience guilt because you made a mistake, only use the first nanosecond of guilt that says to you, ‘you could do more,’ let it motivate you to go learn the lesson, fix it, and do more, but then release the rest, because it’s just going to hold you in place, and it’s kind of a fear strategy, and it’s just not helpful.” So stick with the beginning, and then don’t feel bad, because I didn’t want people to feel bad, number one. And number two, that’s a waste of time and it’s a passive strategy. The other thing I did is I started to learn, and this came from rabbinical school where we studied all the time and argued all the time, I learned that you had to reframe mistakes into experiential learning and experiments. If we were all scientists working in a lab, every single mistake we would look at and say, “Oh, we’re now one mistake closer to the answer, because we’re experimenting.” So that reframing became very powerful, and that became a very powerful attribute in people who became successful: reframing, adapting, and knowing they were meant to change, liking change.

Eric Ressler [00:13:20]: So the whole time you were sharing all those perspectives, I was thinking about how you were talking about it through the lens of individuals. And the whole time I was also thinking this is so directly applicable at the organizational level, for orgs who are trying to move their missions forward, create an impact, grow their fundraising. You talk about differentiation, you talk about experimentation and adapting, and I think these are a lot of the same modalities. But even this entire framing around finding a superpower, and understanding this tension between the psychological safety of conformity and how that’s actually a trap, and that standing apart and doing things differently, and to a degree questioning some of these norms and standards, is actually what allows you to thrive long term. So I’d be curious to hear, have you thought about this at that level, even though your work is more primarily with individuals?

Sandy Gould [00:14:15]: Yes. When I started, I remember I thought of myself, and I would even frame this to people, I’d say, “I’m really a champion of the individual.” When I worked in recruiting at a small boutique agency in Seattle, Washington, I was consulting organizations, large corporations, Microsoft, Amazon, et cetera, and people would say, “Well, are you ever going to join one of those organizations on the inside?” I would say, “Oh no, I’m too much of an individual. I’m too weird. I’m too much of a champion for individuals. I could never do that.” And then eventually I did, and I loved it. But I did bring the spirit of individuality and a focus on human amplification, of which business was a part, or nonprofit mission was a part, as the way I was going to approach it. So I approached it very differently. For me, that made sense.

I remember one day someone was saying to me, “Oh, all of our employees are having this reaction to growth of the organization.” The organization had grown. So suddenly there was a line of people out the door saying, “We want raises.” The CEO said to me, “What is going on?” And the head of marketing asked me the same question. This was the moment I created this concept. I said, “You know what? Think of an organization as just one big person. Really simple model. Just think of it as one big human. It’s like one big collective human. It goes through the same thing, has ego, self-awareness, eyes get opened. So all these people are working on the mission, and suddenly the org is making a lot of money. So they’re like, ‘Oh, I did this,’ which is good. We want them to feel that pride. But with that pride comes ‘compensate me,’ because the org’s now making hundreds of millions. I should be making millions.” That opened a door for me that would continue throughout my career, which is: whenever I wanted to think about what’s going on in the culture, because I’m a student really focused on the culture and understanding it, if I think of it as a person, the model fits. It has an ego, and it contracts, and then it’s successful, and then it has more confidence, then it gets insecure about whether it can maintain that level of success.

A few weeks ago, I went to do a keynote for an offsite of a company I used to work for. I’m now going back to them, and I’ve seen that they’ve doubled in size. So they’ve grown, they’ve had big success, they broke through some big barriers. I showed up to tell them, “I’m so proud of you, and look at this change you created, and look at the superpowers you used to do it. Now you can take all that information and use it to prepare for the next summit up the mountain you’re going to have to go to, and the wall you’re going to have to break through.”

And I realized, and then I could see, they were all nervous. Their leader said to me, “Why are they nervous? We’ve just had success.” I said, “No, that’s when it’s scariest.” Because they’d rather sit on that success instead of have to prove themselves again, number one. Number two, they don’t want to blow it. When you were at the bottom, there was nothing to blow, there was nothing to break, everything was up. But now they’re up, and they don’t want to be the one who loses it or causes the organization to fall back down the mountain. So you have to help them be aware that that’s what’s going on, and then do what I was doing with them, which was pointing to what they had just done. Because this is the other thing that happens. We’re humans, we’re born broken, and we’re neurotics. We spend all of our time on the bad list, the “I didn’t get done” list, instead of what we did get done and what’s good. Famous thing: we all go to sleep at night worrying about what might happen bad tomorrow. We don’t go to sleep pro-worrying about what great things are going to happen tomorrow, but we should. We should actually balance it. So when you do recognition in an organization, like I was doing with them, and say, “Look at the last two years, look at what you managed to overcome,” the reason that’s powerful, it’s nice, it’s a nice thing to do, but that’s not why it’s powerful. It’s powerful because if an individual and a group of people, an organization, all have a collective superpower rating, every time they accomplish something, they realize they can do more. The superpower rating goes up. But if you call it out and recognize it, it goes up even more. And when does it need to really go up? Right before they’re about to take on something really hard, so that they can be reminded, and remind themselves, “We’ve figured this out before, we’re going to figure it out again.” That’s where faith in yourself matters, because you don’t know what the answer is yet.

Great leaders. I remember a great CEO in 2002 or 2003 that I was working for got all their leaders together and said, “Oh, we have to now go from level four to level five of success.” And level four was hard to get to. They said, “How are we going to do it?” And we were all like, “Oh good, he’s going to tell us the answer.” And he goes, “I don’t know.” He said, “But I know everyone in this room can figure it out, because look at how you figured out four.”

Sandy Gould [00:19:05]: I remember looking at him going, “Wow, what a great leader. That was smart.” And we figured it out, and we got to the next level. So your point about individual to org, to me, it is the same blueprint, just expand it out. When you think about encouraging all the things, the most powerful thing being diversity, diversity of thought, I think the difference engine is what drives every human, every group of people, and our life and our world. If you and I were exactly the same, this conversation would be nothing. So you have to cultivate that all the time, because everyone does think they’re different, and they are. We have to help and support that, encourage that. And the more people feel comfortable expressing that, which is why diversity matters so much for communities that are underrepresented and need to be more represented, the more enriched our lives will be. I think difference gives meaning, and that’s a big part of the book too.

Eric Ressler [00:20:00]: So I’m hearing a couple things. One of the things that I’m hearing is that belief is such an important part of this. Not necessarily knowing how you’re going to get to the next level individually or as an organization or for your mission, but believing in yourself, believing in the collective. “Hey, we’ve gotten to level four, so we’re going to get to level five with the same crew.” And reflecting back on that, even myself running Cosmic over the last 16 years, having many breakthroughs and many setbacks, and that ebb and flow of things feeling like they’re gelled and easy and things feeling like they’re not easy: when I don’t have self-confidence individually, or self-confidence as an org, and I lose that belief, where it feels like you’re spinning in place, you can’t get traction, everything feels like it’s going against you, the experiments are all failing, that to me is one of the things that’s hardest to hold onto, that belief that we can figure this out. We haven’t yet, but I know that we can. And I think it’s a hard balance to strike, because you also need to be willing to admit when your ideas are bad or your hypothesis has failed, even though of course you always want it to be the one that’s going to win, that’s going to get you to that next level. So how do you find, and how do you coach and advise folks at the individual level and at the org level, to strike that balance of belief, but also realism around, “Hey, this strategy failed, we need a new one”?

Sandy Gould [00:21:35]: Yeah, that’s a great question. So we all do this interesting thing. We equate confidence and hope and faith with bullshit, and they’re two different things. Faith that you can figure it out, hope that you will, confidence in your ability, those are all about investing in something you can create. Bullshit is saying something is other than what it is.

Authenticity actually is more significant, and so is trust, in order to activate superpowers and the ability to seize opportunity. I remember when I joined the corporate world, one of the first things I experienced was spin. I had to start coaching leaders how to communicate. In the old days when I was growing up, leadership was: know the answer, have confidence, and tell people what to do. But in the emerging generations we’ve found ourselves in, I believe it’s really shifted to be a power learner, adapt, and get the most out of your people, help them figure things out. So it’s the “figure it out,” because we’ve all lived through so much change.

I had to start coaching leaders, and when something bad happened, either they wanted to hide it, or not talk about it, or spin it. I remember I was preparing a leader for a conversation with the company about something bad that happened. They said, “I’m going to tell everyone that it’s okay.” And I said, “How do you know that? What do you mean it’s okay? What does that mean, and how do you know?” And he couldn’t answer the question. I said, “Don’t say anything you don’t know.”

I said, “Also, don’t tell people how to feel. Only say things that are true. And if you don’t acknowledge something as bad, number one, you have lost trust. They stop listening to everything else you say.” So he’s like, “Well, but what do I say?” So I’m going to give you an example. This one company I worked at, we lost a really big deal, and it was a time the company was struggling, so the loss of this deal, this client, was a blow. And they’re like, “What do we say?” I said, “If you knew it was coming, say you knew it was coming, and that you prepared a plan, that you’ve identified other accounts you’re going to replace this account with. Or if you’re going to get it back, that. Or if you don’t know, say, ‘We’re on the road figuring it out, and here’s how we’re going to do that, and we’ll keep you updated as we do.’”

“I don’t know” is a very powerful, honest thing to say. But honesty is more important. First, establish trust, then invite them in to help you figure it out. I said, “Say all those things. You can say, ‘I know we’ll figure it out, I have faith in that,’ but don’t tell people how to feel, and don’t tell people the outcome when you don’t know it.” I also remember one time a CEO was talking about some difficult changes we were making at the org, and they didn’t want to say anything bad. They said, “I don’t want to deflate everyone.” And I said, “But you have to answer honestly. If you don’t know, you don’t know, which is powerful, because you show that it’s okay not to know. And a lot of times we don’t know.”

I said, the other thing is, I had to give this person a rule. I said, “I want to give you a rule. We’re going to call it the politician’s rule. When someone asks you a question, the very first thing you have to say is yes, or no, or whatever the answer is. Yes, no, or X. Do not go on a story. Do not distract or divert. Do not deflect. Because the moment you don’t answer the question in your first word, they don’t even hear your second word. They know you’re not answering the question.” And that rule has served many a leader, and me too, when we are all so tempted as leaders to want to make it okay, or explain context before giving the painful truth. So start with the answer. So someone says, “Did we fire people?” Yes. “Are we going to fire more?” If the answer is yes, yes. And if it’s maybe, maybe. And if it’s we don’t know, we don’t know.

And if we can’t tell you, it’s “we can’t tell you. Why?” So those become really important to that build of trust and confidence. Then once people know they’re in it with you, you’ll figure it out. Now, here’s the other thing I want to address that you said. Stuff is bad sometimes. That’s life. And there’s a great book that a close friend of mine had me read, one of my favorite things, my friend Jason had me read this book, and everyone’s read this book, but I can’t remember the name of it right now. One of his principles is, why do humans avoid pain? It is life. You can’t avoid it. It’s coming for you whether you do or you don’t. And it’s how we learn, and in pain we are forged, that builds us. So recently I was coaching a leadership team, and they’re like, “Oh, we need to be aligned, because we don’t want the team to see us fight.” I’m like, “No, that’s not true. You should be 70 or 80% aligned. You should not be 100%, because diversity should keep breeding different ideas. And everyone knows that no two people or more are 100% anyway. They should see you fight. They should just know that you know how to do it, and how to get to resolution in a way where it’s collective. We’ve come to an agreement, we’ve agreed and committed, we’ve disagreed and committed, we are aligned in the go-forward. That’s what they need to see. If you don’t show them you fight, they just think you’re hiding something, and that lowers trust. But if they see fight, and they’re like, ‘Oh, fight is fine, we get through it and then we have better ideas at the end,’ that is power, because you’ve got to adapt, and adapt will mean friction.” So that’s the other thing. When people say to me, “We’re really off right now, the org feels off,” or “I feel awful, we’re all uncertain,” that is the feeling of your being telling you it’s time to change something. And let yourself feel that way until you change something.

Eric Ressler [00:27:30]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring your ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Eric Ressler [00:28:20]: That rings so true for me. I’m reflecting on some of the harder points in our trajectory. I’ve talked about this before on the show, and I don’t want to get too into it again, but last year was a particularly difficult year for us, and for a lot of social impact organizations, just with all the stuff going on with the funding ecosystem changing, orgs, especially progressive orgs, being under extra scrutiny from the current US administration. And basically we saw a lot of orgs, and I don’t say this judgmentally, essentially freeze up, hunker down and wait, see what’s going on. How do you plan in a year like last year when so much is uncertain and chaotic? And what that does to an agency like ours, that helps organizations through transformational, pivotal moments, is that a lot fewer people are calling folks like us to help them get through those moments. And I had to have a lot of really tough conversations with my team about some of that uncertainty and some of the not knowing, and the reality of, “Hey, here’s where we’re at, here’s the trajectory, here’s what’s going to happen if this doesn’t start to go better, we’re going to have to do pay cuts or reductions.” And I struggle with that a lot, frankly. To figure out, in a time like that where my team is also uncertain, and they’re smart folks, they’re looking at the space and looking at who we are and putting two and two together pretty quickly, there’s an impetus for me to be like, “Don’t worry, it’s going to be okay, we’re going to get through this,” or to paper over the difficulty. And I chose instead to follow a lot of the advice that you just outlined in your earlier response, which was to be transparent about here’s what might happen. We don’t really know what’s going to happen, we can’t make promises because we don’t know. And it’s really hard as a leader to say “we don’t know” or “we’re not sure,” because you want to be able to provide that certainty for your team. “Hey, you’re safe, you’re okay, we’re going to figure this out.” And one of the other things I’ve struggled with too as a leader, that I’ve heard other leaders express to me as well, is you feel a sense of wanting to take care of the team, of wanting to keep them safe. And even, “Hey, it’s not their job sometimes for these folks to figure out how to keep the business alive. They didn’t sign up for that. They signed up for their role.” But I do think there is a shift, and I think a healthy shift if it’s done in the right way, where everyone gets ownership over keeping the ship alive. And this obviously depends very highly on the type of org and the size of the org. But at the end of the day, to your point, an organization is just one organism made up of people. And we’re not in a place, and I think this is healthy, where leadership figures it out, develops a strategy, and it’s just top-down, “hunker down, do your job, and everything will work.” First of all, that’s not how it’s ever been. It’s not going to work in this current world where things are evolving so quickly. It’s not going to be possible. And so I think there’s a tension there for me around, how do I engage my team deeply and authentically without asking them to do things that maybe they didn’t sign up for, that feels like, “Hey, these are high stakes. You hired me as a designer or a developer, you’re asking me about our business strategy now?” Now, what I found is that my team steps up to those and feels good about being included in those levels. But I still think there’s a balance around how there are certain things that leadership probably should be responsible for at the end of the day. And I think everyone’s going to have to find their own balance there. So I’d be curious to hear how you think about advising leaders on where to strike that balance, and how to think about making those choices.

Sandy Gould [00:32:05]: Yeah. That’s a great point, and just a great framing question about that balance, because we’ve had to deal with that, and I’ve had to deal with that at almost every organization I’ve been at.

Okay, a few things. With the kind of social and tectonic world shifts that have happened in the last few years, even going back to COVID, where suddenly survival was mingled with daily existence and no longer a given, you had so many situations where all of us as leaders, and when you are a leader, there is a built-in salvation, savior complex, just like paternal, maternal: protect, take care of, help them, save them, and get them to happiness and safety and survival. And as we all know, no one can save anyone else, generally. So what do you find? You find that you discover what it is you can do to help somebody, and to help empower and unleash them. And that is the most you will do for them, because anything you do to actually save them that doesn’t put agency in their hands is not only secondary, it can become risky, because then it’s a dependency, versus self-sufficiency, which is more foolproof.

If humans are like a tool in the world, this tool is meant to function. So a human is meant to create, their identity is meant to mature, and they have to be the driver of that. We just have to support and equip them. I remember right after COVID, I was training and meeting with a bunch of managers, and I asked them how successful they were in the last few years, and 53% said they failed. I said, “Why?” And they said, “Because we couldn’t make our people feel safe during both COVID and the racism that followed.” And I said, “That means you’re becoming a really good manager, when you realize you can’t do that. All you could do in that situation, and it’s a really good example, is let them know you were there for them, engage them in what they were experiencing, and understand the best ways you could support them in all those situations: being an ally, standing up, helping to drive and unleash and support diversity, guiding them on the things they needed to do to stay safe through COVID, et cetera.” And it’s always the case. So if you think now, over the last year or two, when suddenly the world for many turned upside down again, leaders have to say, “Well, what can we provide?” So transparency, inclusion, co-designing with them where they have the ability to co-design, but then knowing where there’s not enough expertise for co-design, so it’s more like input or awareness, and then where they want you to own more of it.

So if I’m in the house with my parents and we go for a drive, it doesn’t make sense for them to ask me to drive also if I’m eight years old. And if I’m 10 and we have to get out of the house because there’s a fire, again, I don’t think I should be co-designing that process. They should just tell me what to do, and I’ll do it. But then there are other areas where either I’m learning and I can offer input that actually is guidance and material, and then, as I’m even more senior, like senior employees in an organization, or domain experts in an area, then there’s more you can put in their hands. So as an example, I believe in a leadership model around distributed leadership: put as many decisions in the hands of the employees doing the work as you can, because they’re closest to it, and they have the expertise, and they have the context. And then balance with decisions that might be more remote to them, or less familiar, or perhaps tied to bigger-picture elements where there’s different domain expertise required in different context, and then just share and help in learning and teaching that. But you have to invite people and say, “This is what this now means, here’s what we want you to participate in.” And sometimes you have to experiment and see when it doesn’t work. So the last few companies, I’ve had moments where an employee said, “We don’t want to co-design.” A lot of times they want to co-design, but sometimes they’re like, “No, you just tell us the answer.” And that’s fair, right? And then sometimes we put stuff in people’s hands, and then we see that it didn’t work, or they can’t handle it, or they’re handling too much.

So we take it back and say, “This didn’t totally work in the way we wanted it to support you. So that means we just need to do some more build if we’re ready for this kind of co-design. So let’s stage that.” And I’m a big believer in roadmaps. One of the things you made me think of just now: I’ve played Dungeons & Dragons since I was 12, and it’s all about maps. So I think when an organization exists, it should have a map of where it is now, where it was in the last two years, and where it’s going to be in the next two. And it should say one or two things that’ll be changing about the major business and vision, and then the one, two, or three things the people, the process, and the technology will need to do to keep up and to help. That should just be there. And eventually you have all your employees building that together and putting it on the walls as cool art, with milestone moments for offsites and things like that. It makes a huge difference. It really does. It’s the difference between, if you’re driving the car and I’m in the back seat and I’m your kid, and we hit a bump and you didn’t say a word to me, how I’ll react, versus if you told me there’s about to be a bump, don’t worry about it.

So it’s the same thing with organizations, but multiplied. It allows people to know, “Oh, next we’re going to have to adapt more, we go to fewer meetings,” or “we proxy more of our perspective,” or “we need to spend a lot more time sharing our worldviews and aligning them,” or “this part of the company’s most important this year, but then next year that part will be, and everyone gets a turn.” All those things become really helpful, as you’re defining too what unique contributions and unique superpowers the individuals and the teams bring. Because just like we were comparing individual to collective, self-esteem is the same way. There’s corporate self-esteem. So what I found, there was this one point where we had this organization I was at, we were very centralized. There were a lot of satellite offices. We had a new CEO, and we’d moved a lot of decision-making back to the headquarters, but it was a global organization, and of course everyone else felt really excluded and suddenly unimportant and a bit dethroned. So everyone’s like, “What do we do?” And I said, “Well, each one of those offices has an expertise. They have a set of superpowers that we rely on.” Singapore is great at payments, London is great at mobile. We had all these different things. And I said, “We should make that known, because humans are need-based. When they understand we need them in London, because they are mobile experts and mobile is the tip of the spear for our business, they will get a lot more comfortable with their position.” And that worked. That actually worked. You have to build it and make it real. You can’t just say it at a meeting. It has to show up in the decisions you give them to make, and the responsibility and the resources they get. But once we did that, then that became a really strong unifying force, an identity-unifying force for each different team. And it gave them support when they weren’t going to be the center of something going on. But then we were also honest and said, “The headquarters is the headquarters. It is the steering wheel of the organization. So just know that when we do meetings, we’ll make sure we’re super inclusive. Other offices will present, other people will be involved, there’ll be communication.” We designed strategies to support distributed staff, but the headquarters is the headquarters, and that’s where the CEO is. So our CEO made a really smart move, which was, she said, “That is the reality. So we’re going to balance those, but we’re going to be honest with you too. Working in London is not the same as working in wherever the headquarters is.” So I think that learning helped too.

So to your point about teams, it is a lot. This last period of time has been so intense, and we’re in a fractured state of media, we’re in divided nations and worlds, there’s so much conflict. And that’s when you have to get into: everyone has different worldviews. Success for a community and an organization and an individual is when you can understand other worldviews and yours, and connect them, and then see what happens when they come together through their difference to create something different. So I came up with three principles, after trying to moderate a lot of debate about really intense issues over the last two years, that have helped. One was, whenever I’m dealing with parties who are really going into debate, I say, “Let’s focus on getting to unity through division. Let’s make that our goal. What will we decide? What will we go forward with? We’ll do the debate, but the idea is to get to a point of unity.” And then the second one was, because a lot was coming up about being right, who’s right, I said, “How about we just focus on, let’s replace who’s right with human rights, and make that our priority, more than who’s right, because who’s ever right?” And then my third one was, can we enter into a conversation with the goal being, “I’m going to broaden my lens by understanding what you’re thinking,” instead of “I’m going to share what I’m thinking”? And if those are our goals, I think we get to better outcomes. But then, what do we have an opportunity to now create by bringing these different elements together, instead of just a war of worldviews? Which — It’s endless. That doesn’t end.

Eric Ressler [00:42:20]: It’s not constructive, right?

Sandy Gould [00:42:20]: No. There’s a possibility to get to something amazing if we combine what you and I are thinking, and then so on and so forth, and multiply that exponentially. But that has to be your goal. That has to be your framework. Otherwise, all conversations are ridiculous. They’re just me going, “This is my worldview,” and then you go, “This is my worldview,” and I go, “Okay, well, mine’s right,” and you go, “Yeah, mine too. What a coincidence.”

Eric Ressler [00:42:40]: Right. Yeah. We’ve learned, through some work with clients, this concept of constructive disagreement, which I think is basically what you’re describing. And one of the things that stood out to me about that is you have to go into those conversations with the goal not being to prove yourself right, but the goal being to truly, deeply, and fully understand the other party’s point of view, and to really empathize with it. Even if you don’t end up agreeing with it, even at the end of the day you walk away saying, “Hey, you know what? I understand more about your perspective, and I still feel that mine is actually more accurate, or that my idea is the right one, but now I have a better understanding of where you’re coming from and how you got to your idea.”

Sandy Gould [00:43:20]: And it broadens your lens. So early on in my career, after I joined the corporate world and saw this constant debate of who’s right, two principles I formulated based on the logic training I did in rabbinical school. One was, whenever someone would come to me and say, “I’m going to fight with this other team,” my first question, first premise: what are they thinking?

Eric Ressler [00:43:40]: Yeah, right, exactly.

Sandy Gould [00:43:45]: I want you to know what they’re thinking. I want them to know what you’re thinking. Second premise: you can’t challenge an idea until you understand why it might be right.

Eric Ressler [00:43:50]: Yes.

Sandy Gould [00:43:50]: So defend the other side first, then we can talk about the challenge. And then the third one is, you’ve got to be able to debate and battle through things to get to a better conclusion of what happens when they come together. So we all have to be comfortable with that. We have to accept the personal, the passionate, but focus on: we are going to get to this collective shared goal together, that’ll take us further than if we just did it individually.

Eric Ressler [00:44:20]: Right, right. And if you have that shared vision, then there’s something to have a debate about, and we should welcome diverse opinions and ideas and hypotheses around how to get there, and not just pick one and go all in on it. Let’s try a couple things. Now, you can’t always do that, but I think often you can. You don’t need to make a choice that’s like, “Well, we all disagree, so we’re going with this strategy.” How about, we all have different ideas around how to get there, let’s test them and let the world decide which one’s going to win. I think that’s more of a scientific method, experimental approach to doing the work.

Sandy Gould [00:44:50]: I agree. And it leads me to an idea that I want to share, that I came to. Someone said something to me in an interview years ago that made me realize this. I’ve been reading comics since I was eight, right? I read 30 a week. And so I realized, when we share our stories with each other through media, we end up creating ourselves in each other. We’re all walking amalgams of all the people that we’ve met and are in our lives. So when you think about it that way, every time you interact, you’re creating and being created anew. So looking at it as, I’m about to go into a meeting and debate with Eric about whatever, it’s going to become Sandy plus Eric and Eric plus Sandy, and that new equation is more. And that’s the experiential learners that we are. So if we start framing it like that, then anything is possible, because we’ll always come up with something new, we’ll always be able to go somewhere new, because it’s going to be more than just me or you. And that discovery, if you center that, I do think people can do anything, as we’ve seen.

Eric Ressler [00:46:05]: Sandy, I think that’s a great place to wrap up. Before we do, where can folks who are interested in learning more about you follow you, see your work, eventually buy the book, and get a little bit more of this thinking? Because I think it’s so important for people to be considering these things in their journey as individuals, as leaders, as organizations. This is your time to just plug all the things.

Sandy Gould [00:46:25]: Awesome, thank you so much. And for this conversation, I love conversations like this, because they’re transformative, and you do a great job at it. So that mission is really important. I’m glad you’re doing it, because humanity needs it.

Eric Ressler [00:46:40]: Thank you.

Sandy Gould [00:46:40]: We need those activators, which is one of my ideas, about the people who activate us. So my website is sandiegal.com. It’s not live yet, but it will be by the time the book goes out. That’s one. The book will also be on Amazon. You can find out about me on my LinkedIn, I do a lot of posting and videos on LinkedIn about creating, about superpowers, and about the job market and things like that in your career. And on Spider Sandy, which is my Instagram. And more to come in September, the book will be coming out. And then I’m going to be doing videos in a similar format, where I’m interviewing people that are in the book that I’ve interviewed, like Abby Wambach and Bobby Brown, and people who just... Takidra from Waymo, people who I’ve met along the way who really showed me their mission and how it was turning into their superpowers as they were changing the world in some pretty profound ways. So those videos will be out, and then there’ll be one-minute videos too, about different aspects of the book, about superpowers and activating your superpowers.

Eric Ressler [00:47:45]: Very cool. Looking forward to it.

Sandy Gould [00:47:45]: Looking forward to doing all of that with the world. That’s the goal.

Eric Ressler [00:47:50]: Awesome. Thank you, Sandy. This has been great, really enjoyed the conversation, and looking forward to checking out the book when it’s out.

Sandy Gould [00:47:55]: Awesome. You’ll be getting it, so don’t you worry.

Eric Ressler [00:47:55]: All right, man. Thank you for your time today.

Sandy Gould [00:48:00]: Thank you too. Be well.

Eric Ressler [00:48:05]: Okay, cheers. If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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Every leader in every org in the social impact space has its fair share of failures. But for some reason, in this space, we don’t talk about failure a lot. We tend to brush over it or paper over it or diminish it or reframe it. And I think that’s a huge mistake.

Today we are joined by Michelle Moog-Koussa. She is the executive director of the Moog Foundation, a foundation that exists to carry forward the legacy of musician and synthesizer pioneer Bob Moog. And they’re doing something that I think is very interesting. They are embracing failure and the scientific method through the lens of music creation and synthesizers to teach young children and the community at large how to become better people, essentially. Michelle’s built the Moog Foundation from $15,000 and a stack of a bunch of Bob’s early crossed-out notebooks into a 20-year institution that has tens of thousands of students that they’ve served, a world-class museum, an archive — and people have told her along the way to quit, and she never did.

In our conversation, we get into why the social impact sector has a cultural problem with failure, what the scientific method actually demands of leaders, and what Bob Moog’s approach to experimentation can teach us about building organizations that learn instead of organizations that get stuck in planning.

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Episode Highlights:

[00:00:00] Why the social impact sector refuses to talk about failure

[00:02:00] From theremins to a synthesizer that changed music: who Bob Moog was

[00:04:00] How 60,000 CaringBridge messages gave birth to a foundation

[00:07:00] The three pillars: Dr. Bob’s SoundSchool, the Archives, and the Moogseum

[00:12:00] Stepping into a legacy with $15,000 and a steep learning curve

[00:15:00] The sine wave of a career: surviving 2008, COVID, and Hurricane Helene

[00:17:00] “You’re swinging a miniature bat” — and the reframe that changed everything

[00:23:00] Running a nonprofit like a scientist: hypothesis, test, iterate

[00:25:30] The sector embraces the scientific method — except the failure step

[00:27:00] “Mistakes are the portals to discovery”

[00:31:30] Why fear of failure keeps organizations frozen in planning

[00:34:00] Music as a force for community, not isolation

Notable Quotes:

[00:25:30]: “The sector at large does not accept failure with grace.” Eric Ressler

[00:27:15]: “Mistakes are the portals to discovery.” Michelle Moog-Koussa

[00:18:05]: “I don’t have a miniature bat. My bat is so big, I just needed more people to help me swing it.” Michelle Moog-Koussa

[00:30:55]: “I don’t mind that we make mistakes. We’re human. What I do mind is if we don’t learn from them.” Michelle Moog-Koussa

[00:32:50]: “The best idea in the world has zero impact until you actually take it into the world to test it.” Eric Ressler

[00:31:30]: “If it doesn’t work, that just means you’re one step closer to getting it to work.” Michelle Moog-Koussa

Resources & Links:

• The Bob Moog Foundation — Michelle’s foundation; donations, the membership program, the volunteer portal, the online store, and newsletter signup all live here

• The Moogseum — the foundation’s museum in downtown Asheville, North Carolina

• Dr. Bob’s SoundSchool — the foundation’s 10-week second-grade sound-science education program (nearly 40,000 students served)

• CaringBridge — the platform where Bob’s page drew 60,000+ visitors and nearly 4,000 testimonials from 67 countries

• The Orange Peel — the Asheville music venue where Dr. Bob’s SoundSchool students perform their end-of-program concert

• Spectrasonics Bob Moog Tribute Library — a $100 sound bank of 1,300 sounds; all proceeds benefit the foundation

• UJAM Vox Humana — a charity plugin benefiting the Bob Moog Foundation

• Native Instruments Modular Icons — a sound library that benefits the Bob Moog Foundation

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:30]: Michelle Moog-Koussa, thank you so much for joining us on Designing Tomorrow today.

Michelle Moog-Koussa [00:01:30]: Thanks for having me. It’s great to be here.

Eric Ressler [00:01:35]: So for our listeners who are not familiar with the Moog Foundation and Bob Moog, who is a musical icon and possibly even legend, could you start by giving us a little bit of background about Bob and his life, how he lived his life, and how that led ultimately to the foundation being formed?

Michelle Moog-Koussa [00:01:55]: Of course. It’s my favorite thing to talk about. So Bob Moog invented the Moog synthesizer in 1964, and that synthesizer, being the first one that was truly accessible to musicians, went on to revolutionize the face of music. And although that was nearly 70 years ago now, the Moog synthesizer continues to be quite prominent in music of every genre. He started off as a doctorate student in engineering physics and was making theremins on the side, something he had been doing since he was 14 years old. And for anyone in the audience who may not know what a theremin is, a theremin is an early electronic musical instrument, one of the earliest, invented in 1920 by a Russian physicist named Leon Theremin. And when Bob was just a kid, he and his electrical engineer father would make electrical hobby projects together. And Bob at that time fell in love with the theremin and made one.

He made his first one for a science fair when he was 15. And by the time he was 19, he was proficient enough that he was writing articles on how to build them, and then went into business selling assembled theremins and theremin parts. And that eventually led him to the musician who asked him to make a new instrument to make new sounds. That gentleman’s name was Herb Deutsch, and they worked together. And the result was the breadboard prototypes of the Moog synthesizer. The Moog synthesizer went through many iterations and still continues to go through many, many iterations. And Bob went in and out of the company as it was owned by different people. But in the last 25 years of his life, he was working steadily on developing alternative interfaces for synthesizers, developing theremins, and of course developing more synthesizers. And then he did pass away in 2005, actually August 21st of 2005.

And that is when the foundation was born and morphed very nicely into why we were even created. And I will say that Bob was a very humble person. He did not like to think of himself as superior to anybody else. And I don’t think he would’ve ever envisioned the foundation in his name because of that. But what happened when he was quite sick — he had a brain tumor at the end of his life — is that we started a page on CaringBridge for him. And for those of you who are not familiar, CaringBridge is essentially a place where either critically ill or terminally ill people can set up a webpage and communicate with people on their own time, at their own pace, and people can leave messages for them. So it’s a way to communicate without being intrusive to someone who’s quite ill.

And we set up a page there thinking it would just be for maybe 40 people who would be interested in how he was doing. And instead, 60,000 people logged onto that page in the first seven weeks, and then 20,000 people logged on the day he passed away. But even more powerful than those numbers back then in 2005 was the fact that almost 4,000 people left testimonials in the guestbook section. Where in most pages it would be, “We’re thinking of you, we’re praying for you. We learned if you eat blueberries it will help your tumor,” that kind of thing — well, in this particular page for Bob Moog, it was one testimonial after another about how Bob Moog had either changed or totally transformed people’s lives. It was super powerful, with people saying things like, “Because of Bob, I’m a musician. Bob Moog gave me my creative voice. Because of Bob, I’m an engineer.” And it just went on and on like that.

And I will say it was quite a daunting moment for my family and myself because, hearkening back to that humility, my father didn’t talk about his work that much. And when he did, it was never in any grandiose terms. And I don’t think that any of us knew what he had done. We didn’t talk about his work, but we definitely knew the basics, but I don’t think any of us realized the true impact. Those testimonials came from 67 different countries, and we knew that there was something incredibly special there that we wanted to harness and carry forward. The chance to inspire people all over the world just doesn’t come along every day. And here we had a vehicle to do that by continuing his legacy. And that’s where the Bob Moog Foundation was born.

And not surprisingly, our mission is to inspire people of all ages through the intersection of science, music, technology, and innovation. So it’s essentially a mirror image of what Bob himself did for over 50 years. The way that we achieve that mission, we have three main projects. One of them is called Dr. Bob’s SoundSchool. It’s a program that we’ve run for about 12 years through which we teach little kids — second graders, to be exact — about the science of sound through music and technology. It’s a 10-week curriculum that we deliver to entire school districts, and we train the teachers, and the teachers then teach the students. We’ve educated almost 40,000 little kids in that time, and we’ve been really heartened because the program is 10 weeks long, but it’s highly experiential and multisensory. So our goal is that kids are hearing, touching, and seeing sound with every lesson.

We’re really trying to meet the kids where they are in their learning journey and provide the kind of curriculum where the kids will really retain the information. And we have done some assessments and we have found just that — that our curriculum compared to a standard curriculum, there’s much more knowledge retention, which is what we’re looking for. So that’s one program. The other program is the Bob Moog Foundation Archives, which is a vast collection of over 15,000 pieces of archival material that we protect and preserve and share with researchers and journalists and museums. And those two projects, the archive and the education, feed right into our third project, which is the Moogseum in downtown Asheville, North Carolina, which is an outward-facing facility that brings Bob’s legacy alive to inspire people of all ages, and to do so in a way that’s really accessible.

We wanted to make sure it wasn’t just a synth geek fest. It’s really meant for anybody who wants to be inspired by someone who was deeply dedicated and committed to their field and was able to make these huge changes, because we believe as an organization that anybody can affect the world around them, and we want to encourage them to do that.

Eric Ressler [00:09:55]: Just a lovely, in my opinion, origin story for a foundation in the space of social impact, where the current approach to foundations being formed seems to be typically that some individual is highly successful commercially, makes a boatload of money, and starts a foundation as, in the best interpretation, a give-back, but often also a tax advantage. And what strikes me about your foundation and Bob Moog’s legacy and his history is that Bob strikes me as someone who just genuinely loved music and loved technology and loved the intersection of those two things, which speaks to me very directly. And then the foundation was started because of the impact that he had on so many people. It’s really a grassroots foundation, and you all have had the opportunity to take all of the positive impact and the community support and channel that into not only continuing Bob’s legacy, but also building on it and expanding it — taking a lot of the values and the virtues of who Bob was as a person, and even through your leadership and through the staff and the community, built on that and evolved it and expanded on it too.

So I’d love to hear your take, your experience, on what that’s like stepping into a legacy. And I think we mentioned when we were talking earlier about how sometimes people like Bob get reduced down to the key talking points, and almost their humanity gets flattened in a way that is not true to how complex they were as people. So I’d love if you could just share what that journey’s been like for you stepping into the role that you have.

Michelle Moog-Koussa [00:11:45]: It has been a remarkable journey that I am honored every day to be navigating. I’d like to say that Bob Moog forged this big golden path and I get to just walk on it every day. It’s quite extraordinary, and we knew that from the beginning, as I mentioned. That doesn’t mean that we were equipped necessarily to take on this project, but we knew that it needed to be done. And quite honestly, when the opportunity came up, my brother was initially guiding the process. It wasn’t anything like it is now. It was more just a name and a couple of ideas. But then he decided he needed to cycle off and offered it to the rest of the family. And I was amazed I was the only one who stepped forward. And I said to him, “I know I have a big learning curve, but this opportunity cannot be passed up.” So we started with almost no money.

I think we started with $15,000, that’s all we had. And then it was a very steep learning curve of learning what is involved in a nonprofit. We didn’t even have our projects defined, certainly as they are now, much less figuring out some kind of fundraising network.

And it is important to point out that Bob had his ups and downs with his career. He would say that he wasn’t really a businessman, that wasn’t his forte. He was much more focused on musicians and musical interfaces. And as a result, I don’t think the words “rich” and “Bob Moog” would ever go together in the way that most people would think about it. So as you note, this was an effort that was born out of sheer commitment and recognition that the humanity of all of this was so powerful that we had an opportunity to do something very special. This is not the glorification of Bob Moog. It certainly is not a tax shelter or anything like that that you noted. It’s really all about that ability to inspire people all over the world.

Eric Ressler [00:14:20]: What have you learned that either has surprised you most or inspired you most as you’ve stepped into this role and this journey and worked through the early stages of building up a foundation all the way to where you are today, where you have a defined theory of change and programs and a very clearly, and I would say well-articulated, definition of your role in the ecosystem and the purpose? That’s a journey to get there. I’d be curious to hear, what have you learned on this journey about either the power of music or the way that you can have the biggest impact that maybe was surprising or unexpected for you?

Michelle Moog-Koussa [00:15:00]: I would say that if you’re talking about one of the things that I learned the most, I would have to say that this journey has been quite challenging in many different ways. Of course, we went through the 2008 dot-com bubble and things were difficult for us then, and we’ve been through COVID, and we’ve been through Hurricane Helene, and there are other complexities that have come up that have been extremely challenging. And then of course there’s the fundraising part of it — just trying to make it, trying to grow it, trying to figure out who you are. And there have been several times where I’ve wanted to quit, where people around me have encouraged me to quit. And the one thing that I have always come back to is Bob never quit. And things weren’t always easy for him either. I like to say that his career was like a sine wave. It was up and down and up and down, and the ups were really high — and most people know about those ups — and the downs were really low, and a lot of people don’t know about those at all, as you say, because I think the knowledge base focuses on the high accomplishments.

That to me has been so critically instructive: that you don’t give up. And it’s one thing that I share with people, for example, when I’m doing tours at the Moogseum. I like to say that, yeah, Bob Moog was obviously very smart, he was very educated, but I think also as defining for his career and his impact was the fact that he embraced commitment and dedication as strongly as he leaned on his education and his intellect. And that’s something that we can all muster when needed, but that has been a guiding force for me and helped me and the organization get to where we are. And I have found it both deeply instructive and deeply inspiring, because it’s not easy. I remember someone saying to me, “You should give up. You’re trying to hit a home run with a miniature bat.” And he meant that from a business perspective — that we’re trying to do a lot with hardly any money.

And this person encouraged me to quit, and I told him I couldn’t. And he said, “Why?” And I said, “Because this foundation has so much potential. I can taste it. We’re just not there yet, but I can’t just give up on it.” After he left, I thought about what he had said. I do want to consider what people say. And even though I didn’t agree with him, he was being honest, he was being earnest, and I did appreciate that. But then it came to me that I don’t have a miniature bat. My bat is so big, I just needed more people to help me swing it.

Eric Ressler [00:18:15]: Hey friends, real quick before we continue today’s episode — I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

I think something that a lot of executive directors and founders — what you shared with me in your journey — it rings true to my experience even running Cosmic over the last 16 years. And the sine wave, for listeners who maybe didn’t get it: a sine wave is a really fundamental element of synthesizer design and music in general, so applauding your pun there. But that also does feel like my experience, and I think the experience that I hear a lot of our partners who are often executive directors or founders share. And I do think that it’s a really tricky balance in our space, in the social impact space, because there is a lot of burnout. There are a lot of conditions and cultural norms in the system at large that I don’t think is structurally right for the scale and the scope of the missions that a lot of folks are working towards.

And so I do think we should be changing that. We should not accept that this is just going to be hard and that’s just how it is, fully. And at the same time, there is a balance there where we shouldn’t expect it to be easy either. If this were easy, these problems would’ve been solved. Our missions would already have come true decades ago, millennia ago in some cases. And so I think that sine wave balance is one that is tough. And I think for me, one thing that I’ve always known in running Cosmic, and that I see when I talk to a lot of founders like yourself, is that there is this greater purpose or potential that I think folks like us see that outside advisors maybe don’t always understand as deeply if they haven’t ever been in that position themselves. And I’m not saying there aren’t times where spinning things down isn’t the right call.

Sometimes there is a breaking point and a boundary that gets passed enough times, and it’s like, you know what? We had a good run. We’ve made some good impact, and it’s time to close shop. And that’s okay too. I don’t want listeners to come away with the reaction that, well, that’s just how it is and there’s never a time where we should be shutting things down. But there is a spirit of perseverance, of resilience, of just sort of grit at some level that I think is fundamental to running a shop like this too.

Michelle Moog-Koussa [00:21:30]: Yep, I would totally agree with that. And I tell people that all the time. There are certain equations in business that help make things work. And when you don’t have as much of something, you’re going to need more of something else. And for us, it’s like, okay, so you don’t have a ton of money — how are you going to compensate for that? And that is just bearing down and getting the work done. And there were times, especially in the first five and 10 years, when I would work the 60, 70, 80, and occasional hundred-hour work week. I don’t recommend that last one, by the way, for anybody. I think it’s really important to embrace that, recognize what your situation is, and make the equation work, whatever that means. For someone who’s much better funded, it could be a different kind of equation. But for us, it was that grit, as you say, that was an absolute necessary element and continues to be.

Eric Ressler [00:22:30]: I think the other thing that maybe we should touch on a little bit — in channeling Bob, but also in hearing how you’re talking about how you’ve run the foundation — is an almost scientific, experimental philosophy. When you’re inventing new instruments or reimagining them, there must be that kind of experimental intuition in terms of a guiding principle around how to approach it, right? Having a hypothesis, testing it, getting user feedback, iterating, scrapping things altogether, accepting that sometimes you’re going to fail and that’s just part of the process. So there’s that scientific, experimental, entrepreneurial mindset that, in my opinion, is how we should be thinking about running these social impact organizations, whether you’re a nonprofit or a foundation or a funder. This is the way, in my opinion, that we should be thinking about this. And I’d love to hear if that resonates with you, and if so, how you’ve thought about running experiments, iterating, and what some of those aha moments have been in your trajectory.

Michelle Moog-Koussa [00:23:45]: That’s a great point. And I would say that hearkens right back to the heart of Bob Moog’s career and studies and interest. And that is essentially the scientific method, which is something we actually teach in Dr. Bob’s SoundSchool. And the scientific method is: you write down your idea, you test your idea, and you write down the results. And we have a lot of Bob’s schematic notebooks, and we share pages from these with the kids in Dr. Bob’s SoundSchool, particularly the pages where the whole results section is in the middle of the page and he crosses it out and just says “didn’t work.”

Eric Ressler [00:24:20]: Didn’t work.

Michelle Moog-Koussa [00:24:25]: Didn’t work. And the next page he’s trying again. So I find that whole approach really fundamental to growing an organization or a business. Some people may have these one-hit wonders right off the bat, but I think that that is probably the exception. And a lot of organizations are much more iterative, where it is a continuum of trying to figure out what’s working, where you’re getting your highest ROI, focusing on those things while being open to new ideas and constantly incorporating those ideas as much as is applicable for your business.

Eric Ressler [00:25:15]: I think it’s so true. And to talk about the scientific method — one thing I’ve noticed observing the space deeply through my lens, working with a number of different orgs, is that the sector at large does not accept failure with grace. And what I mean by that is that there’s an expectation and a norm and a culture in philanthropy and in social impact that failure is bad. And so what I think we see a lot of times is a lot of orgs are embracing the scientific method when it comes to writing down ideas, developing a hypothesis, testing those things, and listening. But I think where we stop is the most important part of that entire process, which is embracing failure, publishing the results of failure for the sector at large, and not seeing failure as something that’s bad, but an inevitable, constructive part of the process of learning.

And I hope that we can change that in the sector. And I think it’s going to take all sides to do it. I think the dynamic and the power dynamic is that nonprofits who are funded either by major philanthropies or by donors, they don’t want to admit failure because it feels like they’re letting their supporters down. And I think we need to change the narrative around that — around failure is part of the process. It’s a good part of the process. It’s actually the most helpful part of the process, because if we can’t admit when we fail and we gloss over that or we just don’t talk about it, then we’re not really doing this work earnestly. And I’d just be curious to hear, as you teach kids about this process, do we need to reeducate the social impact sector at large around the failure step in the scientific method?

Michelle Moog-Koussa [00:27:05]: I think so. I think that failure or challenges should absolutely be embraced. And I’m reminded of probably my single most favorite saying, just because I have to say it to myself so much, which is: mistakes are the portals to discovery. And in this case, you could say mistakes or failures are challenges — they are our teaching tools. So we need to heed them as much as our successes. And I would agree that being able to share them and show their value is incredibly important. So many people tend to get mired down in them, and I think that just stymies progress.

Eric Ressler [00:27:50]: I’ve even noticed sometimes, and even with myself — this can be a problem that I’m working on — that if you aren’t careful, you can’t actually learn from those failures if you don’t honestly and fully accept them as failures. If you gloss over them and try and reframe them as not a failure — and that’s a slippery slope, because if all you do is focus on the negatives and the failures and you don’t view them constructively and effectively, they can just bring down your mood, your energy, your inspiration. So there’s a balance with this, as with many things in life. But at the same time, this culture around failure I think leads to us not learning and not iterating and not becoming the best version of ourselves and our organizations, if we don’t take a moment to fully embrace, recognize, and accept: this experiment failed.

And here’s maybe why. Here’s a new set of hypotheses around why that experiment may have failed and what we might do differently next time. But what I see sometimes is people reframe or reposition or gloss over these failures as, well, we gave it our best, and, oh, look at all the good things that happened during that failure — and sort of diminish and paper over the failure. And then you don’t fully, truly learn from it because you don’t accept it as a failure, and you don’t go through that next step of, well, what might we do differently next time? So I’d be curious to hear how you’ve dealt with that in your own journey, and how you saw that happen in the scientific method that Bob took, and how your students are now taking it in the classroom setting that you have as one of your programs.

Michelle Moog-Koussa [00:29:35]: Well, I would say at the very beginning, it was harder to surmount the challenges without just kind of beating yourself up about them. But I think as a leader, you recognize, okay, you know what? I’ve only got so much energy. So am I going to put my energy towards being mad, being upset, being self-defeating? Or am I going to take that energy and turn it around and try to forge a more positive path forward for whatever it is? And for me, that’s what it really came down to — that I knew I had to be very careful with how I dispensed my energy. And if I was just going to walk around being sad, that wasn’t going to get us anywhere. And that’s the goal. The goal is to move forward.

And so I have obviously had lots of challenges and failures. And what I started doing was immediately taking the opportunity to have a feedback session after an event that didn’t work out, or whatever it was — a grant application that wasn’t successful — to turn around, gather a group of people together, and then brainstorm what went wrong. And I like to say to my team, I don’t mind that we make mistakes. We’re human. What I do mind is if we don’t learn from them. So that’s my approach: to learn from those mistakes. And of course, again, this is what Bob did. This is what the scientific method is based on. And it’s one thing we really impress on the students of Dr. Bob’s SoundSchool, which is, first of all, no idea is too stupid to write down. All your ideas are valuable. Write them down and then test them out and see what happens and write down the results. And you know what? If it doesn’t work, that just means you’re one step closer to getting it to work. As an example, here’s Bob’s work showing you that’s exactly what he did over and over and over, decades.

Eric Ressler [00:31:40]: I really love that. I really love that. And the other thing I’m reflecting on that I also see — there’s the not-accepting-failure mistake that we can make trying to follow this scientific method. But then there’s also another version of that that I see, which is almost a fear of — I think it’s related to that first thing — a fear of imperfection or a fear of failure keeps people in that write-down stage: the three-year strategic plan that takes 12 months to put together that then doesn’t get tested until the plan is fully dialed. And so we stay in this planning-strategy mode for so long, when the scientific method, and even to a degree a design-thinking methodology, would be more around how quickly can we get these ideas into the market or into a prototype form and get them tested?

Because that’s where the real learning happens. And there’s a balance there too. You don’t want to just go with a half-baked idea that doesn’t have any intention behind it or any thought behind it, but I see other orgs stay frozen in that overintellectualizing, overplanning, overthinking stage. And I can fall trapped to this myself. And what I’ve learned is that the best idea in the world has zero impact until you actually take it into the world to test it and to iterate on it and to see if your idea is solid or not. And I think sometimes that can be another form of a defense mechanism, another form of fear of failure — if you don’t ever actually test your ideas, you can’t fail. And so you stay safe because you don’t take them into the market. So I really love, and I think about this scientific method as a way to think about how to run social impact organizations from various vantage points.

And I think it’s really cool that you all are channeling that through Bob and through music. And I’d actually like to spend a little bit of time, as we work towards wrapping this up, talking about music — the power of music for personal happiness, the power of music for community-level happiness, and then also the power of music for social justice and social change. And so I’d love to hear how you think about that, and also how you see music impacting people, especially young people, in the work that you all are doing.

Michelle Moog-Koussa [00:34:00]: Well, let’s start with what music meant to Bob, because that’s kind of where we’re rooted in. And I will say that he was devoted to the transcendental nature of music as a force — not only for self-expression and self-enjoyment, but particularly as a force that brings people together in community. To the extent that in the late ‘90s he was interviewed and someone asked him what he felt about or saw in the future of electronic music, and what he honed in on is that he was highly concerned that technology had developed to an extent that people could both make and listen to music in isolation, and that if that continued, a great cultural resource would be lost in enjoying music as community. Now, thankfully, live music is alive and well, and we do come together in community hundreds of thousands of times a day around the world around music. So that is the dedication that we are rooted in as well, and what an important force this is for all of us. And part of it is self-expression. You cannot minimize how important that is for people.

We definitely like to feed that, and so did Bob. People would ask him if he was a musician and he would say, “No, I’m a tool maker. I make tools for musicians.” And the musicians were really his beacon. And I think that the reason he felt so strongly about them is he was obviously a very creative guy, but he was also an engineer, and his way of thinking was very linear. Whereas when he connected with these musicians, their mindset is this broad, open expanse, and it’s just a trajectory of exploration for them. And he loved that, and he wanted to provide the tools for that exploration. And I feel like that’s what he felt that he provided — not only providing the tools for sonic exploration, but those tools as vehicles to connect with a larger audience. We don’t talk as much about this in Dr. Bob’s SoundSchool because we are talking to second graders, so we don’t talk about more of this maybe philosophical foundation that we have, but we definitely encourage them to embrace all kinds of music, to embrace all kinds of sound, to think about sound that’s around them, to think about music, where it comes from and how it’s made. And then every year of Dr. Bob’s SoundSchool, all the kids get together and they put on a concert about what they’ve learned.

Eric Ressler [00:37:15]: Very cool.

Michelle Moog-Koussa [00:37:15]: So they actually get to come full circle and provide a musical experience for their parents and teachers, which they are often very thrilled to be able to do, because they do that at the Orange Peel, which is like the hallmark music venue in Asheville, and they feel like rock stars. They get up there and they can feel the power. They’ve got 500 people they’re singing to, and they can feel the power of what they’re doing. So it brings it all very full circle through those moments.

Eric Ressler [00:37:50]: In many ways, I’m reflecting on how learning music, or being introduced to music-making through a synthesizer, is such an awesome and profound musical introduction. Because although a synthesizer — and there’s all kinds of different synthesizers, of course — it can feel overwhelming without proper facilitation or guidance, in many ways it’s the most fundamental, basic, almost molecular building block of music-making, which is just a sound wave or a sine wave. And then it gets manipulated and adjusted. I think one of the things that many people don’t realize about synthesizers is that they’re reductive in nature. It starts with a pure sound wave, and as you’re shaping that sound, you’re reducing things, you’re not adding things, with the exception of maybe some effects like delays or reverbs. But it’s almost like chiseling a block of granite instead of starting from building blocks and building on top of them.

And so it’s a really interesting, experimental, in my opinion, accessible, and equitable introduction to music, because it takes away the structured “here’s the scales, here’s the modes.” And all of that fundamental music knowledge is great too, but this to me feels like a great way to introduce music as an imaginative, discoverable, experimental modality instead of a structured modality — which, if you really want to get serious about making music and pursuing music, you need that part too. Or maybe you don’t need it, but it can be quite helpful as a tool. But that just strikes me as a really interesting and unique way. So I have a first grader who will be a second grader next year, and hopefully she’ll have the opportunity to go through some of your programming. Maybe we’ll connect after the show and figure out a way to make that happen and bring it to her school and to her teachers.

Michelle, before we wrap up, I do want to give you a chance to just plug or promote anything that would be helpful to our listeners who are interested in learning more about the Moog Foundation or your work. Where can people find you online, and what opportunities do people have to get more deeply involved if they’re interested in pursuing that?

Michelle Moog-Koussa [00:40:00]: Oh, thanks for that opportunity. So people can find more about us at moogfoundation.org and moogseum.org. Ways that they can get more involved — the first one won’t be a surprise. Donating to the Bob Moog Foundation is always really powerful. A nonprofit without funding is like a car without fuel. It’s really that simple. So every donation helps empower our work and is crucially important to everything we do. But there are other ways to support. We have a membership program with all kinds of cool perks that people can participate in, also found on our website. Visiting the Moogseum when you’re in Asheville, North Carolina, or in Western North Carolina, or telling your friends and family about the Moogseum, is another powerful way. We also have an online store with all kinds of cool merch, and of course every sale goes to support our projects. And there’s a volunteer portal through the website, and that also has been very powerful for us.

We found some really great volunteers. And I would say two things, one in closing. One is that in-kind donations are also very powerful. If you have any old electronic musical instruments or documentation that can be part of the archive, that’s a great way to support us. We run fundraising raffles four times a year where we raffle off either vintage synthesizers or Eurorack synthesizers. And that’s a really fun way to support us, and those raffles are crucially important for us, so keep your eye out for them. You can sign up for our newsletter through the site and you’ll get notifications of the raffles. Of course, we’re on Facebook and Instagram, you can find out more there as well. I encourage people to do that. That’ll just give you a really good idea of what we’re focusing on day-to-day, week to week. And also for those of you who are into synthesis, Spectrasonics has a product called the Bob Moog Tribute Library that they developed that solely benefits the Bob Moog Foundation. It’s a sound bank of 1,300 sounds made by all these amazing sound designers, and it’s $100, and every bit of it gets donated to us. A company called UJAM also has something like that called Vox Humana. And there are some other companies as well. You can find out more about other companies that support us, including Native Instruments — it has Modular Icons that benefits the Bob Moog Foundation. So if you look on our website under “ways to support us,” you’ll find all of those options as well.

Eric Ressler [00:42:55]: Awesome. Michelle, thank you so much for your time today. This was really inspiring for me and hopefully for our listeners as well. And thank you so much for joining me.

Michelle Moog-Koussa [00:43:05]: Thanks so much for having me. I really appreciated it.

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Every nonprofit leader has told themselves some version of the same story. If funders really understood us, they’d fund us. If the community got what we do, the support would follow.

Jonathan knows that story well. Five years into turning the Seymour Center from a quaint aquarium into a hub for coastal resilience, he can feel the distance between the impact the organization actually has and how the community still sees it. When he started, that distance was massive.

I get why the story is so easy to reach for. It puts the problem out there, with the people who don’t get it, and keeps it away from us.

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But when a leader says they’re having trouble telling their story, it’s almost never a storytelling problem. The identity underneath it was never made clear. The raw ingredients are usually all there. They’ve just never been combined in the right way.

I call this the identity impact gap. The distance between the impact you actually have and how the people you need to influence understand you. Close it, and funding, talent, and trust all get easier. Ignore it, and you can do great work for years while stalling out.

The uncomfortable part is where the responsibility lands. If the people you need don’t get you, that isn’t their failure to pay attention. That’s your work, still unfinished.

So the question I’d put to any leader who feels misunderstood is this: are you closing the gap between who you are and how you’re seen, or waiting for the world to finally catch on?

Episode Highlights:

[00:01:15] The identity impact gap, defined

[00:02:45] The sector myth: do good work and growth takes care of itself

[00:04:05] Why the gap quietly starves your funding

[00:05:05] The two problems bigger than funding

[00:06:20] The Seymour Center’s own gap, in real time

[00:08:20] Why a widening gap can be a sign of growth

[00:12:50] The three pillars: identity, expression, perception

[00:26:35] How organizations drift into autopilot

[00:27:35] Self-diagnosing: “we’re having trouble telling our story”

[00:30:00] “That’s a you problem”

[00:31:05] Asking funders and partners how they’d actually describe you

[00:38:40] Why trust isn’t built on your 990s

Notable Quotes:

[00:04:50]: “You get the first meeting, but never the second. Or people say, yeah, I kind of get what you do, but you get the sense they don’t really understand it. If only they got us, they would support us.” Eric Ressler

[00:06:20]: “The perception of the community is probably like a quaint little aquarium and science museum that my kids go on field trips to. That’s the long history. And we’re becoming this collaborative center for coastal resilience.” Jonathan Hicken

[00:23:10]: “I would urge orgs to figure out: if there was only one thing that everyone could know us for, what might that one thing be? And do a really good job beating that drum.” Eric Ressler

[00:25:20]: “It has to start with a deep understanding of self. Before you can get to expression, before you can get to perception, you have to know yourself.” Jonathan Hicken

[00:30:25]: “Often you’ll hear orgs and leaders shift the blame towards, well, the funders don’t get it, the supporters don’t get it. And it’s like, look, frankly, that’s a you problem.” Eric Ressler

[00:38:40]: “We got our 990s in order, we got our financial docs. And if that’s where we think trust is built alone, then we’re missing a big chunk of it. This identity impact gap, for me, boils down to trust and trust building.” Jonathan Hicken

Resources & Links:

• Seymour Marine Discovery Center — Jonathan Hicken’s organization, used throughout as the working example of an org closing its own gap

• Cosmic — Eric Ressler’s studio; the branded strategy and client work referenced throughout

• Say What You Actually Believe

• Who are you Becoming?

• Claiming Your Role In The Social Impact Ecosystem

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:15]: Alright, Eric. A couple of episodes ago, you floated very loosely this idea of an identity impact gap, and we kind of glossed over it because I’m sure we were talking about something very important. But I remember it stopped me in my tracks, because I related to it so closely. And I wanted to spend today really unpacking this idea, because I think you might be onto something pretty special here. So this identity impact gap, what is it?

Eric Ressler [00:00:30]: So this came from the point of view episode. We introduced it and said, well, I’m sure we’ll do that. So here we are. In short, the identity impact gap is the distance between the actual impact you have as an organization and how the people that you need to influence understand you as an organization.

And basically, my point of view, in my experience, is that the bigger that gap is, the harder it is for you to actually continue to make an impact and grow. And there’s all kinds of other downstream effects too. So it’s who I am as an organization, or who we are as an organization, and what people think of me.

Another way I say this is deeply understanding who you are as an organization, authentically, truly, honestly understanding who you’re becoming as an organization, and then how people understand who you are and who you’re becoming.

Jonathan Hicken [00:01:15]: So I think I understand the fundamental premise of this, and it checks out. It’s like I’m doing some sort of work and I need people to understand that work. Donors, constituents, whatever the people power. And if they don’t understand it, because I’m not communicating it well or for whatever reason, then somehow that’s going to be a problem for me actually doing my work. So let’s unpack that connection. Tell me why that gap actually gets in the way of doing impactful work.

Eric Ressler [00:01:45]: So it shows up in a couple of different ways. The way I think we get here as a sector is because there’s a long-held belief that I’m basically challenging in my assessment here, which is that if we roll up our sleeves and do really good work and we make an impact and we’re really passionate, everything’s going to be okay and we’re going to grow naturally.

Inevitably, of course, what else could happen? But any leader in this space has felt that it’s not quite that simple. And if you want to blame someone for that, it’s basically human psychology, which is that we need to be able to tell compelling, relatable, emotionally charged stories about our work, because so much of how we make decisions as humans comes down to how we think about the world through the lens of story and through the lens of identity.

And that’s how I get here. That’s one of the many reasons why we ended up here. But you asked the question, what does it actually look like? Why is it a problem? Basically, why does this gap exist? And I want to unpack in more detail in a minute how an individual organization gets here.

Jonathan Hicken [00:03:30]: But from my executive director chair, I want to understand: why is this a problem for me?

Eric Ressler [00:03:30]: So the most obvious answer to that is that this is a big problem for people power, and specifically funding. If you are out there and you need funding to support your mission and to make an impact, if this gap exists, it’s going to be a major drag on your ability to do that.

Some symptoms that might show up: you have trouble even getting a meeting with meaningful funders, be that individual high-net-worth donors or institutional funders and philanthropies. Or you get the first meeting, but never the second. Or you get those meetings and people say, yeah, I kind of get what you do, but you get the sense they don’t really understand it, and you feel like they’re just not getting us.

If only they got us, they would support us, right? Those are some of the things that might show up on the funding side. And I don’t want to diminish the funding element, because it’s obviously a really important part of building sustainable organizations and having the resources to meet the scale of the missions that we’re trying to solve.

But I actually think that’s the easy answer. And there are some deeper answers that are, in certain ways, just as impactful from a negative standpoint, if not more so. The second would be your own internal team’s ability to all have clarity on the purpose and the mission and the direction of the organization, and understand their role and their ability and their opportunity to make that happen.

So there’s this internal team alignment and team strategy element to it as well. If this gap exists, it can be a major drag on your capacity, your efficiency, your effectiveness as an organization. So to me, that’s the second major problem. And then the third would be your ability to attract and retain the right team members and the right talent internally, but also with partner organizations or peers or anyone else in your social impact ecosystem. So yes, funding is a major reason for this, but actually those other two are equally, if not more, important.

Jonathan Hicken [00:06:20]: So I’m boiling this down to clarity, and it’s clarity of who I am and everybody else understanding that same thing. And that kind of checks out. Even at the Seymour Center, I feel like we actually have some of this gap right now.

I think it’s closing. But the perception of the community is probably like a quaint little aquarium and science museum that my kids go on field trips to. That’s the long history. And we’re becoming this collaborative center for coastal resilience, which comes with a lot of different work and meaning.

And so when I rolled out this vision and started working on it, that gap was huge. It was massive. And we’re closing that, and people are starting to understand it. But I do remember these early conversations with donors and partners being like, wait, what are you doing?

Eric Ressler [00:07:15]: So you’re describing a very common scenario. And a really important point in this is that I want listeners and viewers to understand that this gap is not a static thing that you close and you’re done. It’s alive, it’s in motion, it’s evolving, and it changes depending on how the world is changing, what the state of play looks like in your ecosystem, and where you’re going as an organization.

So you’re a great example. You come in as a new executive director for the Seymour Center, and you have a new vision for what the organization would be, who you’re becoming as an organization. And I remember, because we’ve been friends and colleagues throughout that whole trajectory, which is about five years, almost to the day.

And I applaud you for this. You came in and you had a vision. You had a hunch. Hunch is good. But you also spent a lot of time getting settled in, listening and understanding. And I think anytime you come in as a new ED, there’s going to be some surprises, right?

Where you sign up for one thing and you’re like, whoa, they’re going to open up the closet and here’s all the skeletons, right? And so that might change your hunt for your strategy. But nonetheless, you came in not to just run this place business as usual. You came in with a mandate to reimagine it.

And so in those moments, of course, the gap is going to get bigger, as it should. And that’s actually a good sign that the gap is big, because what it basically means is that who you’ve been and who you are is very different than who you’re becoming. And that means this gap is going to open, and you need to do some things to close it in order to reach those goals and bring the people along who you need alongside you to make sure you can actually do it.

Jonathan Hicken [00:09:00]: Yeah, in a way. Fundamentally, the gap doesn’t always necessarily mean you’re totally screwed, right? It doesn’t mean your organization is going to fail. This is not a terrible thing, necessarily. In fact, you can create that gap strategically. You can create that gap with a purpose, as long as you’re closing it.

Eric Ressler [00:09:25]: Right. And as long as you’re doing the work to close it, you can create that gap deliberately, which is kind of what I did. And you should create those, because really, the gap in its best form is a sign of growth or a pivot in a meaningful way. If there’s no gap ever, you’re basically just stalled out.

Jonathan Hicken [00:09:45]: I was trying to imagine, is there a version of this where someone is totally transforming and that gap never widens? I think the best version of this is that you, as a leader, are intentionally creating big gaps and then filling them and then creating the next big gap, meaning either you’re making a major pivot or a major growth move as a strategic choice, and then you’re doing all the right work to ensure that you’re bringing people along on that journey.

And that’s healthy, which is why I think it’s very important to say the gap can be a problem, but only if you’re not acting on it. I sometimes think of my job as being a problem maker, which is weird, right? In my role. But just to give you an example, we rolled out this new exhibit, it’s largely digital.

The problem being that we can rotate the content that’s in that exhibit regularly. And in doing that, I created a problem for the organization, which was, now we’ve got to create the content to get it in there. But I created this problem that, once we solve it well, we’ll have tremendous power. But anyway, creating this gap, the identity impact gap, especially during moments of transformation, can be a deliberate choice, as long as you’re prepared to then close it.

Eric Ressler [00:11:05]: So here’s a metaphor that maybe will work for folks. Let’s say you have some major health goals. Maybe you want to lose weight, or gain a certain amount of muscle, or you want to be able to run a 5K in X number of minutes. That’s a strategic goal that you set out.

And by setting that goal, there’s immediately a gap or a void that gets opened, which is, well, I can’t, I’m not that yet. So people have this perception of me as being slow or overweight or not muscular, whatever the delta is there. And then there’s a set of choices that you have to make. There’s a burden that you have to fulfill to make the changes and the choices that you have to make in order to reach that goal.

Jonathan Hicken [00:11:55]: Right. So anytime you’re going to make a major change, as an individual or as an organization, by necessity it’s going to create a lot of new activities and needs and responsibilities to get there. And I am going to belabor that metaphor, because I think there’s something to it, where it’s like, okay, I actually happen to think I’m about 10 pounds overweight right now.

I want to lose 10 pounds, for my weight goals. And so I’ve created this gap. My goal is to lose 10 pounds. And you kind of laid out that there are three parts of this. It’s like who I am, how I express it, and how other people receive it. So to use this metaphor: who I am is 10 pounds overweight. How I’m expressing it is maybe the choices I’m making to get healthier. And then, does everybody else around me perceive me as healthy and fit?

I think that generally works. Let’s break down those pillars in a little bit more detail.

Eric Ressler [00:12:59]: That would be helpful. So I think about them as, you basically use the pillar words. The first is really identity. Another way to think about that would be strategic clarity. It’s just, who actually are we? And what I find is that orgs can get there on their own sometimes. And what I mean by that is, often if you ask an org or a leader, there are a lot of different ways they might answer, depending on where they are in their growth as an organization.

So early on it might be, oh, well, we’re just getting started. We don’t actually know who we are. We have a thesis about who we are, or there’s usually some kind of problem that you are trying to solve when you start a social impact organization. And usually when you first start, the problem is pretty small and pretty specific, in most cases, not always.

Sometimes people will start with big audacious goals to do XYZ, right? But then that shifts over time. So you might have a lot of strategic clarity early on, but that might change, because the conditions of the world change, or the conditions of the fundraising ecosystem change, or the conditions of your particular issue area change. That initial strategic clarity and identity may also need to change.

And I think that happens more than we want to admit in this sector. We get stubborn sometimes in our missions, in our visions and who we are. And we don’t think forward enough about what does the mission actually need right now and how can we best serve that mission. So that’s one pillar. The second pillar is expression, which is, once you have that strategic clarity, how are you expressing it internally and externally to the people that matter for your mission?

And this comes into everything from brand identity and visual communication to your overall marketing communications, to the way you present in meetings, to the way you talk to your team. How are you expressing and articulating that strategic clarity, that identity, and how are you doing that consistently enough and compellingly enough that it sticks?

Because that leads to the third, which is, how are you actually understood and perceived? Because if those first two aren’t strong, you will be misunderstood or missed entirely, or perceived inaccurately or not fully. So people won’t really understand exactly who you are. People won’t really understand what your true impact is. People certainly won’t understand what your impact potential is, what you might do if X, Y, and Z were true.

And so you can start to see how these three elements reinforce one another, and that by strengthening them, it starts to get this flywheel effect.

Jonathan Hicken [00:15:35]: And I can see how actually this gap could erode trust. It could be proactively eroding trust.

Eric Ressler [00:15:55]: Right. Because inherently we make a promise as organizations, either to a donor or to a constituent or to whomever, or a partner. And if that promise is perceived differently than the promise we think we’re making, then whatever we’re delivering is going to not fulfill the expectation of that particular audience. Well, I think what you just described is a perfect example of where maybe the strategic clarity is good, or the identity is good, but the expression of that identity is not being done well.

So people have attached themselves and their understanding to your old identity. You’ve got a whole new idea, and maybe you can relate to this. The Seymour Center: a whole new vision, a whole new understanding internally around who you’re becoming. But the people that you want to influence and that you need to support your mission don’t understand that, because it’s not been communicated well or consistently enough.

So they’re like, wait, I thought the Seymour Center was a cool coastal museum for my kids to come to. And you’ve got this bigger idea, this much bigger idea. So I think, frankly, you are dealing with that perception shift, and you’re doing a good job at addressing it in many ways. But I would guess that there’s a number of people in our community who don’t know the new story of the Seymour Center yet.

Jonathan Hicken [00:17:20]: Yeah, that’s for sure. And one question I have for you is, when you talked about the expression piece, you’re talking largely about marketing and outward communications.

Eric Ressler [00:17:20]: I think outward communications is certainly a big part of it. But it’s also any touchpoint, any opportunity where people are learning about your organization, which, yes, is often going to happen through your brand and your website and your marketing communications, but it’s also happening every day when you’re out talking to people.

When you’re just doing your work, when your board member is, or when a visitor is telling the story of the Seymour Center. Are they telling your story of the Seymour Center, or are they reinforcing an old one of a cool aquarium for kids on the West Side?

Jonathan Hicken [00:18:05]: I just want to be clear, is this an equation? Like identity, self, sense of self, plus or times expression equals perception. Or do these three pillars move and act independently of one another?

Eric Ressler [00:18:05]: It’s a little bit of both. I’ve never thought about it that way, in terms of the equation, the way that you just laid it out. But it’s not wrong necessarily. Because tease that out a little bit: if you do the work to really have strategic clarity and understand yourself at an identity level, which I think we should spend more time talking about, and you do a really good job with your expression of that, the understanding, the perception of your organization is going to improve and be aligned.

And so it is sort of that simple, if you really want to distill it. But I could also imagine perception shifting without those two pieces of the equation moving much at all. The world could change. Circumstances can change. Your community or your constituents themselves may change. And so, in real time, I’m realizing that’s not a dependent variable, to use the statisticians’ term.

Jonathan Hicken [00:19:15]: Right, that’s the way I think about it. This is a very fluid thing that you should be considering at all times. And so a fundamental takeaway for me is I should be constantly aware of these things. At minimum, I need to be honing my awareness for who we are and who we’re becoming, how we’re communicating that, and how the community is perceiving it. I need to have my finger on those pulses at all times.

Eric Ressler [00:19:40]: And my sense is that a lot of orgs often fail at that last step, which is how are we perceived and how are we understood. Because what we see a lot of times when working with clients on branded strategy work is that orgs will have a sense of how people perceive them.

But when we independently interview those same people, they have a very different story. And it just happens for a lot of reasons. Sometimes people don’t want to hurt your feelings, so they tell you something and they tell us something else. Or you just haven’t asked in a long time and you’re making a lot of assumptions in this space.

Jonathan Hicken [00:20:20]: Is this something that’s unique to this line of work?

Eric Ressler [00:20:35]: I would say yes and no. I think this same identity impact gap could apply to any corporate startup or any business or any organization. But I think what does make it distinct is that in the corporate world, the people that you need to support you and the people that you are communicating with are the same people often, right?

You are selling a product to customers. And so there’s a lot of work done around customer and user understanding and surveys and so on. Our work is often a little bit more complex than that, in the sense that the people who are funding the work are often not the same people that you are helping. Or even if you are a social enterprise and you are selling products, there are just more stakeholders and there’s more complexity in the overall ecosystem, because you are not just trying to make money or to earn income and revenue.

You are also trying to create an impact. And there are a lot more players. And so the story is a little more complex. So I do think at a high level it works. But I think our framework is definitely tailored specifically to social impact organizations.

Jonathan Hicken [00:21:45]: It begs the question. You mentioned funders and constituents as these two audiences. So the identity impact gap could be different for each of those two audiences. Or the distance of that gap could be different for those two audiences.

Eric Ressler [00:21:45]: Absolutely. And what I think you will see often is that even the story that you tell your less concrete constituents or your beneficiaries, the people you are helping, they may have a slightly different understanding of your identity than someone who’s a deep funder or partner or board member.

And I think that’s okay to a degree. And actually, I’m glad we went here, because I’ve been thinking about something a lot lately. One of the things we deal with in our client work a lot is that people feel like they’re having trouble telling their whole story, because they’re trying to tell, oh, we do this, but we do this too, and this is really important.

And here’s why. These stories get really complex, really fast. That’s just the nature of doing social impact work at some level. It’s the nature of doing, especially, systems-level work, where you do see how your role in the ecosystem affects everyone else’s role. And as an org doing this work, you can see that clearly, because you live it every day.

And I think that leads to a sense of, well, we must tell our whole story. And I actually think that can be a problem, because if that story gets so complex, you’re having a hard time telling it. And I would actually urge orgs to be really good about figuring out, if there was only one thing that everyone could know us for, what might that one thing be?

And do a really good job beating that drum, because getting people to understand who you are is hard enough when the story is simple. But when the story is complex, forget it. And that actually reminds me of you. Here I go, slamming strategic plans again. But when we try to shove everything into a strategic plan or a mission statement or something, it gets off the rails quickly. And this is another example of that.

And on the mission statement or the vision statement thing, my sense is a lot of orgs think they do have that strategic clarity. Well, we have a mission statement. We’ve got our vision statement. We’ve got our strategic plan. We’re doing all the right things. But I think there’s actually a really big difference between those motions and actually having strategic clarity.

And this boils down to, in our sector, we are on our best behavior. We’re trying to do the right things. We’re trying to do the best practices, and having a strategic plan and having a mission and vision statement, all best practices. And look, I’m not saying you shouldn’t have all those things. All I’m saying is we work with a lot of orgs that have all those things, that have done that work, and they’ve done it well, and they still don’t have strategic clarity, and they still don’t have clarity from the people that they need to support their mission.

Jonathan Hicken [00:24:55]: So we’re using the word clarity. We’re using this word awareness. And this just makes me draw a parallel to almost like self work, like almost therapy-style work, of being aware of who I am and how I show up and my impact on others around me, this deep sense of self. And to me, that’s kind of what you’re describing here.

It has to start with a deep understanding of self, in my opinion. Before you can get to expression, before you can get to perception, you have to know yourself.

Eric Ressler [00:25:20]: So 100% agree. And I would also say that this is why I use the word identity. It’s not just because I’m a brand guy, but to me it really does come down to organizational identity and even, to a degree, individual identity from the leadership team.

And I also think about this a lot as, identity is kind of upstream of all these other things, because if you don’t have that identity piece solid, and let’s use your example or your metaphor, personal work: if you don’t know who you are deeply, and you’re not honest about that, and you don’t do the deep work, even work with the professional to figure some of that stuff out.

How can you possibly know who you want to become and who you should become and where, because you don’t even really know where you’re starting from. And so you can delude yourself, and I think we do this individually, and I think we do this at an organizational level, into, well, we’re this kind of org.

And you create these belief systems about who you are. But if they don’t match reality, you’re deluding yourself at some level. There’s this sense of almost autopilot, right? That you can go on as a person and you just get through your day. You just go through the motions, and you can lose sense of that identity. And the same thing happens for organizations. You can just click into autopilot mode.

Sometimes you can be on that track for years without revisiting some of these questions. And then what’s happening is this gap is growing and you’re not aware of it. And so you’re spinning out, you’re stalling out, you’re feeling like there’s a loss of momentum, or like you’re just going through the motions. I’ve felt like this running Cosmic before.

Jonathan Hicken [00:27:20]: Many times I’ve felt like this individually before, where sometimes you’ll just have a moment of clarity and you’re like, what am I going to do? This is who I want to be. Or as a board. So I think that metaphor holds up there for me. So how do I know, first of all, that I have the gap? For listeners who are trying to self-diagnose right now, where do we look first?

Eric Ressler [00:27:45]: So I would say that most people are aware there’s a problem. They’re not going to think about it in this identity impact gap framework, because they haven’t heard of it yet. But what we hear people say is, we’re having trouble telling our story. It’s one of the most common things that people come to us with.

And that, honestly, is usually not only a storytelling problem. The problem there is not usually that their identity is perfectly solid, their strategic clarity is fully dialed in, everyone’s aligned on their team, and they just have no one who can tell that story. That very rarely happens. I’ll just tell you, it does every once in a while.

And I’m not saying storytelling isn’t an art, it is. But usually, again, identity is upstream of that. So usually the reason people are having trouble telling that story is because they haven’t done that identity work properly. They’re usually 70% of the way there on their own or so, and they kind of call it good at that point.

And they haven’t done the deeper work of really getting true and clear about the distinction of what really actually does set us apart, what is the unique role in our ecosystem that we can fully name and claim? And how do we articulate that, what is our actual secret sauce and best offering, and what can we do in a way that no one else can do it in this sector?

That kind of deep work that people, I think, oftentimes over-index on. Well, the problem is real and worth solving. We’ve had some impact. Our team is really passionate about this work. Great. All those things are amazing. Please never turn those things off. But that’s not enough to have strategic clarity or to be differentiated as an organization.

And so I think you have to build on top of those things and really get honest and clear about your strengths and your weaknesses, and then figure out which of those are worth addressing, which are worth leaning into, what things might be worth shedding. So to me, when people come to us and they say we’re having trouble telling our story, that’s a big red flag. There’s probably some identity issues.

I think the other thing that people might find is, people don’t get us. People just don’t seem to understand who we are. They have trouble understanding our work. They have trouble understanding our impact. Half the time, our team doesn’t even tell our story the same way. Our board doesn’t even know what we do.

Jonathan Hicken [00:30:00]: These would be signs to me that there’s a pretty big gap. Something that I’ve heard on other nonprofits I’ve worked with, other boards I’ve served on, is this the classic, if only everybody understood, imagine what would be possible? And then there’s the accountability piece, where often you’ll hear orgs and leaders shift the blame towards, oh, well, the funders don’t get it.

Eric Ressler [00:30:25]: Yeah. Oh, the supporters don’t get it. They don’t see it. It’s like, look, frankly, that’s a you problem. If they don’t get it or see it, maybe it’s because there’s not anything there. Or the way it’s there is not, what I often see is a lot of the raw ingredients are there, but they just haven’t been combined in quite the right way.

Jonathan Hicken [00:30:45]: So those are some of the times I’ve seen it. And so I’m still thinking about the Seymour Center case, and how do we continue to close the gap. And actually the podcast I launched for the Seymour Center is part of that. And some of the new exhibits we’ve put up are part of that.

But I’m starting to think, how do I close that gap in the best way possible? Where do I start? We’ve talked about identity, and for most of us it starts there, doing that deep sort of inner organizational work. But what other tools in the tool belt are there to start to close the gap?

Eric Ressler [00:31:25]: I think a big one that I see a lot of people miss is that perception and understanding piece: how are we actually perceived by the people that we need to bring alongside us to do our work? And this can be easier for us to do than internal orgs, but having conversations that are honest, and asking people, hey, how do you think about our work?

If you had to describe us to a colleague, how would you describe us? And just get a sense of the way that other people articulate who you are, which is almost more important and more powerful than how you do it. And actually, sometimes other people are going to do a better job at articulating that. We often will do interviews and it’s like, that’s gold.

We’re going to take that and embed that in the narrative. And we do this both internally and externally. So ideally, if you wanted to try and repeat some of our processes in-house, you would go have conversations with your funders and conversations with your partners and conversations with your staff. But you have to be careful about how you do it.

Because if you don’t do it right, people don’t want to insult you, people don’t want to bring you down. And so you have to come in and say, hey, look, we’re actually having trouble with this right now. And the best way that you could support us would be to be fully transparent.

We’ve got thick skin. Let’s talk about, who are we? What are our strengths? What are our weaknesses? Where do you see us being better than anyone else, or being best served or best fit for this role? Where are you confused? Where are you legitimately confused about what you’re not aware of? Did you realize this?

These kinds of open-ended conversations, where you become fully present and open, a deep listener, and then you start to look for patterns and start to see, well, everyone has a slightly different story of who we are, or everyone gets this part but doesn’t understand this part. Is that good? Is that bad?

Do we want to really be known for that part? It’s okay that no one knows about this program that’s super impactful, but if we tried to weave it into our narrative, we just make it confusing and convoluted. And that’s where it becomes a little bit of an art and not just a science. I can imagine there’s a little bit of danger in there too, right?

Where, especially in a funding situation, you run the risk of introducing some doubt. And this is maybe where having an outside partner or vendor to help do the work might actually help, because then you’re not unintentionally presenting doubt to a funder. You could see that, right?

Hey, I don’t know, who am I? Who do you think I am? It’s totally sensitive. And the way that we approach that, being third party helps, for sure. But also, we usually interview funders who are deep partners, who are almost embedded to such a level of partnership that they’re basically part of the team.

They want to see the org grow, and they know this is going to help them do that. Or funders who have not funded but have had meetings, that can be gold. Like, why not? Why didn’t you? So in the aggregate, how did we collectively get here, and what is the impact if we collectively solve it?

I mean, we touched on it briefly, but I really do think the main reason we get here as a sector is two things. One, this long-held belief that I don’t think is true, that if we do good work, everything will work out. If you build it, they will come. And it’s just not how the world works.

And there may be some edge cases where that was true. But if you start to peel back those case studies, you’ll realize that they were all really good at this identity and that gap. So that’s one strongly held incorrect belief in the sector that I hope we can start to shift the narrative around, and not in a way that I want to bring people down, just, hey, let’s be pragmatic about this.

This is not how the world works. So let’s understand that and use it skillfully. And then the second, related to that one, is passion. There’s a lot of, we’re doing good work, we’re doing meaningful work, and we’re passionate about it. And so that passion can actually become a problem. If that means you’re hiring people because of their level of passion and not necessarily the skill level that’s needed on the team. Or people can see a really passionate person and want to let you down easy, and don’t actually give you the harsh feedback that would help you grow.

That shows up in a lot of different ways. And there’s really not incentives for anyone other than you as a leader to fix this problem. And so you get into this autopilot mode where you’re putting fires out, you’re just going for the next grant. You’re working on this program, you’ve got a team problem.

And it takes stepping back and doing this work fully. It’s a big major move. And so I’m also not suggesting that you do this every day. I think you should have a pulse on it every day. But there are times in your natural growth cycle where it’s time to sit down and really do this work deeply.

And I think that’s probably true of personal work too. I don’t think reinventing yourself every week is sustainable. You’ve got to do this work in seasons, where it’s like, okay, I’m going to become this next version of myself, and here’s how I’m going to get there. And then you do the work every day to get there.

And so, let’s imagine a world in which we collectively solve this. We all collectively close the identity impact gap. Let’s imagine that world together. How does the sector change? If we’re in that imaginative state, funders and organizations paired perfectly, and those resources are there and significantly more effectively deployed, because we are funding the right org for the right job at the right time.

That org knows themselves so well that they are not just efficient, but highly effective in their work. Hopefully what I would see as a downstream effect of that would be more dollars into the sector, because there’s more proof of impact, there’s more confidence in the space, and we start to actually solve some of these problems that we’ve been trying to solve, sometimes for decades, if not centuries, or problems that are arising right now, because there’s no shortage of new problems being solved all the time.

So, in short, the sector at large becomes significantly more impactful, significantly more effective. And I would even argue much more joyful to be part of, and I would say more trusted. There’s the, I kind of talked about how this gap probably leads to eroding trust. And so if we’re all doing that to a certain degree in the sector right now, then in a sense it’s, yeah, no wonder there is a mistrust of the sector from some people right now.

And so the question really is to you: what happens to the sector when trust rises? And I think you answered that, which is, more money flowing in. Because otherwise, you could have the most perfect fit between funder and fundee possible, but if it’s the same dollars and cents in the system, then what are we even really doing?

Jonathan Hicken [00:38:45]: Exactly. That starts to get into bigger topics around spend-down and how philanthropy should be part of society at large. And I love going deep and esoteric on those things. But at the end of the day, how much control do you have over those things, unless you’re an org that is specifically working on trying to change the sector at large? Put your effort towards fixing this gap, and it’s going to be significantly more pragmatic and effective for you. And then you can deliver on your impact at a higher level.

Eric Ressler [00:39:05]: Yeah, man. You know, this trust thing, I’m stuck on that, because we think about trust as, how do we earn trust? We got our 990s in order and we got our financial docs. And of course we need those, because that’s preventing fraud, and I’m for that. And if that’s where we think trust is built alone or demonstrated, then we’re missing a big chunk of it. And I think this identity impact gap, for me, boils down to trust and trust building.

Jonathan Hicken [00:39:50]: I think that’s a strong takeaway. And I think that if you do it well, it’s going to help you earn that trust, and to deserve it, and to do it more fully. So yeah, I would agree. And I think, at the end of the day, you are making a promise to the people on your team and outside of your team, and the people that you’re helping, why you exist as an organization, the impact that you’re going to deliver.

And the more that you can actually do that and articulate that clearly and be really clear about that yourself, it just makes everything work better. Anything else we need to know about the identity impact gap that we haven’t touched on? I’m sure we’re going to do some follow-up episodes on this one, but I feel like we hit it pretty good for today.

Eric Ressler [00:40:25]: So, yeah, thanks for digging into it with me.

Jonathan Hicken [00:40:25]: Yeah, this is awesome. Thanks, Eric.

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Most leaders know how to fight through a crisis. Almost nobody’s ready for the moment things start working.

That’s where Jonathan finds himself. Five years into running the Seymour Center, the survival years behind him. Funding’s solid. The team’s humming. He walks the halls, thinks “we’re good,” and tells me that stability feels strange. Almost uncomfortable. Like a problem he doesn’t have the muscle for yet.

I get it. The instinct, once you’ve arrived, is to protect what’s working. Slip into business-as-usual mode. Play the safe, incremental game.

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But here’s what I keep seeing after 15 years: that’s exactly how good organizations stall out. The bold, experimental swings are what built the momentum in the first place, and they’re the first thing leaders quietly retire the moment things feel stable.

So the real discipline is refusing to coast. Building from a place of stability instead of scarcity, while you still have the calm to think clearly.

The question I’d put to any leader who’s finally hit their stride: are you using this moment to make your boldest move yet, or just trying to hold onto the one you already made?

Episode Highlights:

[00:00:40] Five years in, and everything’s finally working
[00:01:35] Momentum is a different kind of problem
[00:04:45] Two buckets: funding and visibility
[00:07:30] Imagining the next level of the Seymour Center
[00:10:45] Three viable paths, one hard choice
[00:11:30] Why not go all in on all of them?
[00:16:40] Play it safe, or make the bold bet?
[00:19:05] Build from stability, not scarcity
[00:20:10] The trap of business as usual
[00:23:05] Owning your wins in front of funders
[00:24:00] Why funders actually decide on vibes
[00:26:55] Don’t skip the celebration
[00:29:10] What got you here won’t get you there
[00:30:30] Better choices come from a place of calm

Notable Quotes:

[00:02:55]: “There’s this moment recently where I was like, I’ve never felt this before. What do I do with this? It feels like momentum.” Jonathan Hicken

[00:19:15]: “How do I make sure not to lose the opportunity to build from a place of stability instead of scarcity? That’s fundamentally the question here.” Eric Ressler

[00:19:35]: “It’s a little strange, walking through the halls and being like, we’re good. This is working. That’s a strange feeling.” Jonathan Hicken

[00:20:35]: “The trap would be, okay, it’s working now, we just move into business-as-usual mode. That’s how orgs stall out a lot of times.” Eric Ressler

[00:28:55]: “Keep the foot on the gas, and lean into what I know has worked — which has been big, creative, different, bold swings.” Jonathan Hicken

[00:29:10]: “What got you here may not be what gets you to the next level. So you have to be open to that too.” Eric Ressler

Resources & Links:

• Seymour Marine Discovery Center — Jonathan’s organization; the “collaborative center for coastal resilience” discussed throughout, including the headline Blue Whale Skeleton project mentioned at [00:02:35]

• Julie Packard — founding Executive Director of the Monterey Bay Aquarium and guest of the Seymour Center’s first live podcast, referenced at [00:12:20]

• Live podcast episode with Julie Packard — mentioned at [00:12:20]

• Cosmic (Design by Cosmic) — Eric’s creative agency, referenced in the mid-roll and throughout

• Settlers of Catan — board game referenced at [00:17:05] in the game-theory analogy

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:45]: Eric, I find myself in this strange and beautiful and unexpected place — five years into my executive directorship at the Seymour Center. And everything’s working. We’ve got some momentum, and I’ve been wrestling with what to do with this momentum. And I imagine we’ve got listeners who are in similar positions.

Eric Ressler [00:01:20]: Right. You’ve made some really good choices, you’ve gotten some good funding, you’re humming. And there’s this question we all ask: how do I take best advantage of this moment? I love this, man. First of all, clearly all of our listeners are similarly positioned, because they take our advice every day and they’re just humming along, making more money than they ever thought they would, making their missions happen. I joke, but I do think we spend a lot of time thinking about how to solve problems in this space, and this is a different flavor of problem — which is, we’ve arrived. We’ve hit our mission goals, we’ve hit a stride, we’ve got some momentum. There’s still work to do. There’s still problems, of course. But how do we take that momentum and best leverage it for future growth? That’s what you’re saying.

Jonathan Hicken [00:01:55]: That’s exactly right. So let me set the stage for the Seymour Center — and then I want some of your coaching. I want you to help me think this through. Be careful what you wish for, man. Abridged history: 2021, five years ago, I start. More centers still closed due to the pandemic. A lot of the early years were just rebuild, rebase — get back to business. The middle years were really about establishing this new vision of becoming, though we didn’t articulate it at the time, a collaborative center for coastal resilience. The last couple of years have been about testing and trying and prototyping and getting a few really big projects off the ground — including some great new exhibits, the podcast, and this headline Blue Whale Skeleton project. All of these things have happened and are going really well. Visitation’s up, funding’s in a good position. The team is solid. And there’s this moment recently where I was like, I’ve never felt this before. What do I do with this? It feels like momentum. And truly, I’ve been thinking about how to take advantage of it.

Eric Ressler [00:03:15]: Awesome, man. Well, first of all — congrats.

Jonathan Hicken [00:03:15]: Thank you.

Eric Ressler [00:03:15]: It’s an awesome position to be in, and a well-deserved one. Let me just ask: what’s on your plate? What ideas are in the hopper, where you’re like, we’ve arrived here, there’s still work to do on these things, but generally progress is being made? Because what I’m also hearing is that although you’re highly involved in a lot of these things, your teams running them are on track. So now you kind of need to tap the next thing.

Jonathan Hicken [00:03:45]: That’s exactly right. And again, the team is really incredible. There’s a lot of our work that doesn’t require me at all, which is a very privileged place to be in. And we have this case for support, which we did with Cosmic. So we have a couple of the next big things lined up. And yet the question still remains: where do I put my time? The place I immediately go is fundraising. Now we’ve got demonstration — proof of the capacity and ability to execute on big things. So how do I leverage that to bring in more money for the next big thing? That’s the obvious one.

Eric Ressler [00:04:30]: Of course. But you also need something to fundraise toward. I’m not saying you’re done, or that there aren’t plenty of things to fund that just need general operating support. But you also need a compelling story about who you’re becoming. And I think you’re still not done stepping into the role that you’ve set up for yourself, from an identity perspective. Would you agree?

Jonathan Hicken [00:04:50]: I agree. So I’ve been thinking about my time lately in two buckets: funding and visibility. What are the two things that I can uniquely do for this organization that nobody else on my team either can or has the time to do? Funding and visibility are the two things that fall into that bucket. And under visibility, I’d also think about reputation and the ecosystem and all of that.

Eric Ressler [00:05:25]: Okay. So fundraising and visibility are your two main priorities as executive director. Where do you think there’s still room to grow in both of those — personally, and also in terms of where you spend your energy and time?

Jonathan Hicken [00:05:35]: On the fundraising side, I think we’ve established enough credibility that we could go after some more aggressive gifts for some more speculative projects. What I mean is, I’ve got this vision for a new educational experience for high school students, which we don’t have right now, which would fill a very important gap in the community. And I think we’ve built the credibility to approach a funder and say, hey, help us pilot this for three years. Three years ago, without the momentum we have now, that would have been a much more difficult conversation.

Eric Ressler [00:06:15]: Right, right, right. And then what about on the visibility side?

Jonathan Hicken [00:06:20]: I’ve known for years that visibility for the Seymour Center has been a weakness. Marketing, brand awareness. Even the actual space — for listeners who aren’t in Santa Cruz, we’re on the cusp of the edge of town. You’re not going to pass it. You’re definitely not passing it by mistake. No, this is not a place you’re just going to stumble upon. You have to deliberately choose to come here.

Eric Ressler [00:06:40]: Which is part of its appeal. It’s like a little crown jewel on that side of town.

Jonathan Hicken [00:06:45]: Gorgeous setting. People come here for the setting a lot of the time. And yet visibility — that’s a problem. For museums or science centers located in their downtowns, they get a lot of happenstance traffic. Right. We’re a destination, so that doesn’t happen. We’ve got a couple of core programs that are well known within specific circles — field trips for local schools, well known in that circle. But otherwise, generally, it’s like, oh, I think I’ve heard of that. My belief is that with more visibility we could strengthen the business and advance impact.

Eric Ressler [00:07:30]: In situations like this, I find it helpful to go into more of an imaginative state, versus a pragmatic, constraints-based mode of thinking — which is important too. But let’s imagine for a second you break into the next category or level, whatever word you want to use. How would you describe that next level, from a fundraising standpoint and from a visibility standpoint? Let’s take each. What would that look like for you?

Jonathan Hicken [00:08:00]: On the fundraising side, it would be major transformations of the physical space and major new programmatic development — new and sustainable education programs, and the funding to do those things.

Eric Ressler [00:08:15]: But structurally, on the fundraising side, are we talking about multi-year general operating grants, or major, almost capital-campaign-style fundraising, or a mix of those two?

Jonathan Hicken [00:08:25]: Probably a mix of those two.

Eric Ressler [00:08:25]: And what about on the visibility side?

Jonathan Hicken [00:08:25]: On the visibility side, what success looks like is more visitorship. Because with more visitorship, that strengthens the economic side of things — ticket sales, memberships, and so on. That’s going to provide a certain level of earned income that could sustain the operational level, but it also helps us deliver on this greater idea for impact that we have, which is to help this community become more environmentally resilient to a changing ocean and planet.

Eric Ressler [00:09:05]: Right. And what’s in your way right now on both of those, in your mind?

Jonathan Hicken [00:09:05]: On the fundraising side, it’s credibility, which I think we’re earning. So, progress there. And I think it’s a better brand story and brand presence. Those two things are really true. And I think we’ve improved on those things, partly due to Cosmic’s help in the last couple of years.

Eric Ressler [00:09:35]: I’d put way more credit in your plate than ours on that, frankly. We’ve helped with some of the strategy behind the execution, and you’ve taken those ideas and run with them and done a really good job there.

Eric Ressler [00:09:45]: And what’s striking me is that these two categories are really self-reinforcing.

Jonathan Hicken [00:09:50]: Oh, for sure.

Eric Ressler [00:09:50]: Which is not a coincidence. A lot of the things that are going to be better for visibility are going to be better for fundraising too, and vice versa. So I guess what I’m trying to understand is — and I’m getting a little more clarity now — I can’t taste what the future looks like for the Seymour Center in your description. I can’t smell it. It doesn’t feel tangible enough for me. And maybe that’s because it’s still emerging. You’re in this imaginative state where it’s not fully penciled out yet. You have some ideas around what it might be, but do you have more detail in your brain? Do you have a particular project in mind? Do I have a particular... I really wish our funding were 60% earned revenue instead of only 40% — or, I get the gist of it, but what does it really look like for you?

Jonathan Hicken [00:10:40]: Good. I see where we’re going with this. Bringing it back to: how do we make the most of momentum? Part of what I’ve been struggling with is that I actually have a couple of options. A couple of things I could be doing.

Eric Ressler [00:10:55]: So you see multiple paths.

Jonathan Hicken [00:10:55]: I see multiple paths. One of the themes for the team this year is enhancing the gathering space. So one angle is go all out on fundraising for physical improvements to the space. Another is to go all out on building out this new educational program. Another would be to go all out on Seymour Studios and the media play. All three of these paths are viable. And one of my fundamental questions is: how do I ascertain which one is the best to go after?

Eric Ressler [00:11:30]: Counter question — why choose just one?

Jonathan Hicken [00:11:30]: It’s kind of like, as the great Ron Swanson from Parks and Recreation once said, never half-ass two things, whole-ass one thing.

Eric Ressler [00:11:45]: Yeah, it’s a strategy. I’m not necessarily saying it’s wrong, but the reason I ask is because it’s similar to the fundraising-versus-visibility thing. I see how all of those things might reinforce each other. Especially the gathering and the media side — especially if visibility is a big element to it, putting a bunch of time and effort into making the space more badass. But no one comes. Not a good use of time. And you said visitation’s up, so obviously you’re already working on that. But I can see how — I think back to something you recently did, which I thought was really cool. The first, and I think so far only, live podcast, with Julie Packard at the Seymour Center, in the room. We got to set it up with a beautiful ocean background. And it was incredible. We had like 8,000 people there. Like that, right? And to me, we’ve talked about this on the show before: when we look at the strengths that the Seymour Center has to offer, undeniably one of those strengths is the physical space. That is an asset that many orgs would be so thrilled to have. And you’ve done a really good job of utilizing that. And also a really good job of not just over-indexing on, well, it’s a museum, come to the museum, see the exhibits, and that’s the whole Seymour Center brand. Obviously it’s so much more than that. And you’re building a lot on that foundation. But if you’re becoming a center for coastal resilience, and you need to educate and influence people, and you’re doing that digitally — I also think we’re in a time where in-person gathering is becoming... we’re rediscovering how important that was in our lives.

Jonathan Hicken [00:13:25]: So what I’m hearing you say is there’s a fourth option on the table, which is to create more opportunities for gathering, on top of making the gathering place even cooler.

Eric Ressler [00:13:35]: Yeah. And I think you kind of have to do both. Because as much as the space is really cool already, I can imagine a version — especially if we’re in this imaginative state — where there’s more of that, where it feels like more than just an exhibit museum. Which it already does, don’t get me wrong. In the early days you were talking about bringing coffee carts here, and food that’s still coming.

Jonathan Hicken [00:13:55]: We do have food now, but we don’t have the coffee cart yet. So let’s zoom this out — because I could talk about the Seymour Center for ages, but what I want to extract here is: what is the exercise we’re doing to help an executive director, aka me, make sense of what to do with this momentum? What we’re doing naturally is talking about high-impact work. And high-impact work in this case has already been somewhat defined by doing this work. We did this work already. We made the case for support. We know what our core initiatives are. So the main takeaway I’m hearing is: Jonathan, don’t overthink this. You’ve got the path. Just go do it now.

Eric Ressler [00:14:50]: Hey friends. Real quick before we continue today’s episode — I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at Design by Cosmic. All right — back to today’s conversation.

Eric Ressler [00:15:40]: Okay, I don’t know if this is going to track, but I’m going to give it a shot. I’ve been thinking a lot about strategy and what that word actually means. We’ve done a lot of episodes about that recently, and I’ve thought about this new — call it a metaphor, or a mental model for strategy — which is: if you think about it like a game, almost like game theory of strategy, where there’s a certain set of rules and constraints within any game. You have those two, in real life or in the center, and there is a goal. You want to win. What does winning look like for the Seymour Center? That’s essentially your vision, your impact statement, your theory of change. So, given all that’s true, how are you going to best play the game? What moves are you actually going to make? Are you going to take the safe moves? That’s a strategy — you’re going the tortoise way, where you’re keeping that momentum and every year incrementally improving. Or are you going to make a big, bold bet that could cost you the game, or could take you to the finish line and deliver that impact more quickly? I don’t know if that’s helpful for listeners, but to me, when we think about strategy, you think about it a lot in terms of strategic planning, or decks or docs that you share with your team. But at the end of the day, it’s really just the choices that you make to try and win the game.

Jonathan Hicken [00:17:05]: I love that. That metaphor works really well for me. And I’m thinking of Settlers of Catan here. I do load up on wool like nobody wants wool. Everyone’s got too much sheep, man. So we have this other factor, which is this new expanse I’ve mentioned in another episode — it’s right there. And I need to figure out how to right-size that new expense. I look ahead and I’m like, I don’t think playing the tortoise game here is going to solve that problem.

Eric Ressler [00:17:40]: If you just start to graph it out year over year, that expense doesn’t go away.

Jonathan Hicken [00:17:45]: And so even as we’re talking this through — this is kind of a moment of, okay, each of those opportunities I just laid out have probably differing revenue potentials. And I know I need to solve this expense problem. So really — should the episode be over? Am I just like, I’ve got to work on the one that’s going to bring in the most money?

Eric Ressler [00:18:00]: It reminds me of, pay down your debts before you make new investments. Not nearly as fun, but probably the responsible choice. But I don’t know — I’m going to push back on that a little bit. because, you need to have a solution to this new revenue reality that you find yourself in unexpectedly. But is the safe way to stay on track the way to do that? Or is that where you need to get creative, to create a whole new source of revenue, or to elevate? Because I respect the strategic clarity that you have already. And what I’m hearing you wrestle with is: where do I now put my energy and time investment to spearhead the things I have in motion? But they’re all through the lens of science solution — Santa Cruz — and through your mission, and your understanding of who you are and who you’re becoming. So you’ve done that, a lot of that foundational work. So what I’m hearing you say is: okay, now what? Now, how do I take that momentum? It’s working. And how do I make sure not to lose the opportunity to build from a place of stability instead of scarcity?

Jonathan Hicken [00:19:20]: That’s it. That’s fundamentally the question here. And I find myself wrestling, because I’m getting almost a little antsy. Where it’s a little strange, walking through the halls and being like, we’re good. This is working. That’s a strange feeling. And also it feels like a big choice to make. It feels like a bit of a burden to say, I could develop this, or that, or maybe a little bit of all of them. And I’ve got to make the right choice here.

Eric Ressler [00:20:05]: So here’s what I’m reflecting on. Hearing you say that — how did you get there? You got there not by doing all the things that were best practices or standard or expected, or based on the old perception of the Seymour Center as an entity. You did it by thinking bigger, taking risks, being experimental, learning about what worked, listening deeply with the community. So to me, you got there not by business as usual. So the trap would be: okay, it’s working now, we just move into business-as-usual mode. That’s how orgs stall out a lot of times. So I would — obviously with intention and deep thought and listening — think about how do I now take what’s working and elevate it. So we’ve got some visibility through the pod and through some of these things. What’s the next level of that look like? And always checking that against: does that deliver more impact for the people that I care about, or is that just not a good use of my time? And then from the fundraising side, when you do those other parts well, opportunities for fundraising naturally present themselves. Because you’ve got a new big project you want to fund, or because you’ve got something you’re just so excited about — you can’t help but have that excitement influence other people who are aligned with your mission, your values. So you can solve all those problems at once.

Jonathan Hicken [00:21:35]: One thing that comes to mind, which all of us executive directors have to think about, is making sure that what we’re personally motivated by and what’s best for the organization are in alignment.

Eric Ressler [00:21:50]: Exactly. And that’s why I put that little clause: check back on your impact. Because at some level, every decision needs to be defendable against your goals for impact. And that’s really the distinction between a true social impact organization and an org that’s claiming that — and it’s basically just lip service.

Jonathan Hicken [00:22:10]: When it comes to funding, this might actually be a moment where the sector — and I’m going to over-generalize here — the sector might find itself challenged. And what I mean is, we are not unique in the sense that we’re doing something that’s working and we’ve gotten to a good place. That happens for a lot of us. And also, in the sector, we’re collaborative. We often avoid taking full responsibility for really great results. We want to share in that win, share in that success. Maybe humility starts to factor in. And so do we miss out on these opportunities to leverage that momentum because we’re not taking credit? You know what I’m saying? That’s where my mind was going. I’ve got to go in front of a funder and be like, we did that. We owned it. We did that, and we could do it again. And there’s a certain level of confidence and boldness that’s going to be required of me in order to take advantage of the fundraising opportunity and the momentum right now.

Eric Ressler [00:23:25]: And I think what I’m hearing is that, although you guys in many cases either did do all of that on your own — you at least led that work — but maybe you also did it in partnership with some other orgs.

Jonathan Hicken [00:23:35]: Absolutely. And that was more of a reflection on the sector. Is this something that happens? It’s a question to you.

Eric Ressler [00:23:45]: I see this in a lot of different ways. What I generally see when people are pitching funders and generating a case for support, and we get this feedback — sometimes we need more evidence, we need more stats, we need more impact metrics. And I think some of that matters. I think we do need to be levelheaded about this work. It can’t be a purely emotional act, and I don’t think that stuff matters as much as we all think it does. Because at the end of the day, when you look at how people actually make decisions — even funders who claim to be very evidence-based — highly simplified, it comes down to vibes. I’m just going to say it. Yeah. Relationships, relationships, network. Do they feel it? Can they feel it? Do they resonate with the vision that you’ve put out, and do they want to be part of making that continue to come to life? At the end of the day, it’s really that simple. Now — do they have to feel that you’re credible in order to make that choice? Yes. Do you have to have a good reputation? Do you have to be able to defend your credibility? All of that is true. But what you’re also saying is, you have to be willing to claim the wins. And I do sometimes see orgs who have trouble doing that. And I do think you have to be careful about how — I’ve also seen orgs try and claim things where, yo, you were one of the groups that did this, but this group actually led this thing. So I also sometimes see orgs come in and claim ownership beyond what is true and authentic. And luckily I don’t see that too often.

Jonathan Hicken [00:25:25]: And this is not a binary, where you’re taking all the credit or you’re failing and not taking anything. There is a way to sort of claim your credit in a broader sense.

Eric Ressler [00:25:35]: But I think, to take it back to you — and I hear you’re trying to think about this sector-wide too — I think you should be proud of the things that you should be proud of, and you should be good at telling those stories. But I wouldn’t over-index on that, because I think what people really want is to be inspired about what they can help you build. So if you can tell a really good story about what that is, who you’re becoming, and how you’re doing that, and what opportunities people have to come alongside you to make that happen — that’s how I would think about it.

Jonathan Hicken [00:26:05]: Yeah. And I realize, for me, on a personal level — what do I do with all of this momentum? I think there’s two things that come to mind. One, I wonder if I should have already had the answer to this question before the momentum hit. There’s a part of me that wishes, oh, now, if I were a few steps further down the road here, I could take better advantage of this moment. But I didn’t. And so here I am. And I’ve got a couple of good ideas. I know all of these ideas are viable. So really the work that I need to do right now is determine the financial and impact possibility in each of these lanes. Yeah, I mean—

Eric Ressler [00:26:55]: The other thing I’d just say is: don’t skip the celebration. Take a moment and be like, we did this — for you, for your team, for the people who have supported you. Because I do think that is actually something we’re not very good at, at times, in this sector: celebrating the wins. And this work can be hard. It can be tiresome. People burn out all the time. Not saying that’s happening for you all, but part of that is because in the sector, we naturally have a tendency to solve the next problem, get to the next level. And that’s good to a degree. And I struggle with this myself too. Don’t get me wrong. But I think taking the time to be like, hey, we did that. I even look at some of the stuff that we do today as an agency, and where we are, and it’s really easy for me to fall into, oh, this thing’s not right, this thing’s not right, we are not here. We didn’t hit this goal. But also, if you told me 16 years ago I’d be doing what I do today, I’d be like, crazy. I freaking killed it. So my off-the-cuff advice here is: sit with that. Celebrate it. Pat yourself on the back. Do the same for you and your team. And then take advantage of this opportunity that you have to be in this position of stability. And then get back to the imagination table. And to me, that’s my favorite table to be at. I think it is for you too. So — hopefully that’s helpful.

Jonathan Hicken [00:28:25]: Well, another takeaway here is — a few of the takeaways so far have been: celebrating wins is a big one. Two is, trust myself and trust the work that I’ve already done, and that there are some great ideas on the table now. Three: don’t fall into the trap of not going out a pilot. Because maybe this is an inflection point where some organizations take a wrong turn by not keeping moving. So keep the foot on the gas, and lean into what I know I’m good at and what I know has worked — which has been big, creative, different, bold swings.

Eric Ressler [00:29:10]: Yeah. And I would say one thing that complicates that last takeaway: what got you here may not be what gets you to the next level. So you have to be open to that too. I’ve noticed that leaders and orgs will get to a certain level, and a strategy got them there. And that worked, and they’re like, well, that’s our strategy, and we’re going to stick to it because we’ve seen it work — but it’s not actually the right strategy for the next level. I don’t know if that’s true for you at this stage.

Jonathan Hicken [00:29:35]: Well, it is, in the sense that a lot of the first few years have been about establishing the strategy. And the question in front of me right now is not, what’s my strategy? The question is, what’s my tactic that’s actually going to help us execute most quickly and most effectively?

Eric Ressler [00:29:50]: And I’m also hearing: do I try and do many things, or just one thing? Where do you put that allocation of time and energy and resources? Which can be different for everyone.

Jonathan Hicken [00:30:00]: Yeah. That’s not a sweeping generalization there. So for those leaders who find themselves in this position with momentum — what advice would you give them to take the most advantage of it?

Eric Ressler [00:30:15]: To me, if you’re in a position of stability, you could also start to think about: now we can start to make investments — not necessarily even financial investments. Put everything on the table. Where are we strong? Where are we weak? And what moves am I going to play in the game next? That’s the way I would really think about it. And then take advantage of your organizational nervous system — a state of being calm, cool, and collected, and make better choices because of that. Because you can make better, more imaginative and more creative choices in those moments than when you’re up with your back against the wall, and you’re more in that survival mode. Those decisions are often not the ones that are actually going to help you get to the next level. And so when you’re in this state, you have a little bit more luxury in time and space to think big, to think creatively, to rethink, to be introspective, to do deeper listening. Now, you don’t want to go so far down that path that you stall out, but you get to make decisions from a different point of view, which I think is a really cool opportunity. So I would take advantage of it.

Jonathan Hicken [00:31:35]: Well — thank you for coaching me through this. What I’m taking away is, for all of us in this position: there’s an element of being true to yourself, recognizing what got you here, being humble that it might not be the same thing that gets you to the next place — but trusting in yourself and in your team, because you wouldn’t be here, unless there was something good there. I think taking the time to appreciate, but also to reflect and to plan — that’s a luxury. We don’t always have to take advantage of that. And then also own your wins — obviously in a respectful way, of the ecosystem and other contributors — but own the wins, and don’t be afraid to tell funders about them. Yeah.

Eric Ressler [00:32:25]: I think that’s great advice. And I hope that everyone who’s listening gets a chance to be in that state, because I know when I’ve been in that state, it just feels really good. And then it leads to just more goodness.

Jonathan Hicken [00:32:35]: Yeah. All right. Well, thanks for helping me think through this, Eric.

Eric Ressler [00:32:40]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you — and thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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Ask ten leaders where culture comes from and you’ll get two answers. One camp says you design it. The other says it’s emergent, that it grows out of the people you hire and the most you can do is set a few guardrails and hope.

I land on the design side. The decisions you make, the way you handle a hard moment, the standards you keep, all of it hardens over time into the way things get done here. You’re choosing that, whether you mean to or not.

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Jonathan comes at it from the other end. For him it starts with the people. Hire the ones who already embody the culture you want, almost without trying, and the rest emerges from there.

The longer we talked, the less those two views competed. Culture is shaped by who you bring onto the team, and it’s shaped by the choices you make once they’re here. Both are true, and neither one holds up without the other.

So the question I’d put to any leader is simple. Are you building the culture you claim to want through the decisions you make every day, or are you just hoping the right people showed up?

Episode Highlights:

[00:00:01] Is culture designed, or does it emerge on its own?
[00:02:14] You never check the box and call your culture “done”
[00:03:22] Why it always starts with who you hire
[00:05:15] The counter-narrative: American work culture is broken
[00:08:35] Untraining the 60-hour week and the four-day work week experiment
[00:11:00] Two philosophies: people-first vs. decisions-first
[00:13:19] Who carries the flag for culture on your team
[00:15:19] The hardest call: firing a high performer who’s a culture misfit
[00:17:12] How good short-term decisions quietly erode culture
[00:20:38] Stop handing your team the solution — protect their ownership
[00:24:36] What last year’s “grind year” cost, and how to unravel it
[00:26:14] Guardrails: scorecards and “the Seymour Way”
[00:29:44] Psychological safety and the freedom to fail
[00:30:31] Seasons of grinding and seasons of rest
[00:31:25] If you ask your team to grind, do you have to grind too?

Notable Quotes:

[00:05:45]: “I think work culture in general, especially speaking from an American standpoint, is bullshit.” Eric Ressler

[00:02:30]: “It’s like nature versus nurture. I don’t entirely agree that you can design it. It always starts with the people.” Jonathan Hicken

[00:15:50]: “The best SaaS companies were the ones who are like, ‘Hey, your results do not make up for the fact that you’re being an asshole, you’re out.’” Jonathan Hicken

[00:23:55]: “Culture is built by the consistent decisions and actions that you make as an org, not by your value statement or your posters.” Eric Ressler

[00:26:50]: “We recently started calling it the Seymour Way rather than core values. Because I can’t actually tell somebody what their values are. What I can say is, ‘This is how we do it here.’” Jonathan Hicken

[00:31:50]: “Anytime I’m asking the whole team to grind, I feel a moral obligation to grind just as hard, if not harder, than the rest of the team.” Eric Ressler

[00:32:45]: “A culture of trust is one where the team could see, ‘Oh, Eric needs a break and he’s taking a break, and I’ve got his back.’” Jonathan Hicken

Resources & Links:

• The Five Dysfunctions of a Team by Patrick Lencioni — referenced at [00:29:51] on how a lack of trust unravels a team.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:00]: All right, Jonathan, we’ve got kind of a meaty one here today. And today we’re going to be talking about organizational culture. And where this is coming from for me is, as you know, we work with a number of different orgs and we’re exposed to a lot of different cultures. And we’re lucky because we work with awesome teams and mostly awesome cultures. But over the years, you can imagine I’ve also seen some maybe not so healthy cultures. And it started to get me thinking, and I’ve thought about this a lot, what is it that creates good culture within any organization, but especially within a social impact organization? And what is it that leads to bad culture within an organization? And I know that you’ve been very intentionally designing your culture, and I’m using that word very intentionally myself because I do think culture is something that you design either by choice or by accident.

And I have some ideas that are formulating around how the sector might think about this differently and even some reflections around where some of my culture is not where I’d like it to be at Cosmic and reflections on how did it get there and what am I going to do to change it? So are you down?

Jonathan Hicken [00:01:05]: I’m so down. Let’s go.

Eric Ressler [00:01:15]: So let’s talk about first, how do you think about culture at the Seymour Center? And maybe even you’ve been in a number of different social impact orgs, some with healthier cultures, some with maybe not so healthy cultures. What’s your take on all of this?

Jonathan Hicken [00:01:30]: Yeah. Let me just set the stage as a beginning. So as we record this, I’m coming up on five years of my position here as executive director of the Seymour Center. And when I started, there was some staff that I stepped into supervising and a culture existed and no shade on that culture, but it wasn’t the culture I wanted. And now five years later, it feels like I’ve got the culture I want. And so I’ve been reflecting on it. In fact, even earlier today, I was doing some preparation for a staff meeting to sort of put all these pieces together. And I felt incredibly proud because I was like, “We’re there. We got this culture.” And I know it’s a snapshot in time. I can’t —

Eric Ressler [00:02:10]: You never checked that box and we’re done with our culture now.

Jonathan Hicken [00:02:15]: Yeah, did it. No. And so I’m feeling really grateful for what we have right now. And so I’ve just been thinking about what do I need to do to sustain that? So I think about culture in a couple of ways. One, it’s like nature versus nurture. I don’t entirely agree that you can design it.

Eric Ressler [00:02:35]: Okay.

Jonathan Hicken [00:02:35]: I think that it is emergent as much as you can put some things in place for that culture to emerge and sort of to guide it or put some guardrails on it. I think so much of it is emergent from things that you can’t control. But one thing is for certain, it always starts with the people. And so hiring the right people for your team, hiring the kind of people who naturally embody the kind of culture you want without even really trying is the single most important thing you can do to design your culture.

Eric Ressler [00:03:15]: Okay. So your claim here is that culture is emergent and culture is built sort of bottom up based on the people who you hire, and it just kind of evolves naturally on its own.

Jonathan Hicken [00:03:20]: 100%. Now I do think that executive directors, CEOs, leaders, they can tip the scale potentially in a way that others can’t. But you as an executive director, you cannot create the culture alone. I’ll stand on that soapbox. You cannot do it alone.

Eric Ressler [00:03:40]: Okay. So I think we have slightly different takes on this actually. And I think that our ideas are not totally at odds with one another. But I actually think that culture is something that you design. And I do agree that the people that are part of the team largely shape that culture. But I also think that the decisions that you make as a leader or as a team or both, and the way that you handle challenges, setbacks, situations, create a spoken or unspoken set of norms and values and ways of doing things that become the culture. And that it emerges based on a series of choices and things that develop, and then they just become the way it works here. And so to me, I agree it’s shaped by people, but I also think it’s shaped by norms and standards and this is how we handle situations like this here.

Jonathan Hicken [00:04:45]: All right. So I think that these things are compatible.

Eric Ressler [00:04:50]: I think so too.

Jonathan Hicken [00:04:50]: Yeah. And this is all semantic, but real quick, I think that when I say you can’t design it, what I’m saying is you can’t put the inspirational poster on the wall and be like, boom, we got our culture. Collaboration.

Eric Ressler [00:05:00]: Right.

Jonathan Hicken [00:05:00]: So I agree with you to a degree that it’s emergent in the sense that it is an accumulation of all these small moments. But I don’t always think you can force those things.

Eric Ressler [00:05:10]: I agree. Now I want to take this up just one level to kind of shape the rest of our conversation here, which is that my hope with this episode is that we can inspire a new counter-narrative and a new norm and a standard for what culture at social impact organizations is, which is kind of a big aim, but it starts with conversations like this. And the reason I say that — and I think this is actually something that’s emerging outside of social impact. I’m dropping an F-bomb for this one, Edith, you better watch out. I think work culture in general, especially speaking from an American standpoint, is bullshit. I think that the way that this has emerged in my professional lifetime is not always working towards a constructive and effective and, I will say, sustainable and healthy way to work.

Jonathan Hicken [00:06:05]: Okay. I don’t think we need to spend a ton of time on that, but unpack what you mean by that.

Eric Ressler [00:06:10]: So here’s what I see in the worst case in social impact especially, but just more broadly as it relates to organizational culture. Value around hustle, value around efficiency, value around urgency, a sense that you always have to be connected, always thinking. Not enough work-life balance, scarcity, bad power dynamics, no room for calmness, no room for space, no room for creativity, no room for failure, no room for experimentation. This is obviously not true at every org, but a lot of our work culture more broadly has been shaped in this way because of the conditions at large in, let’s just say, the world. And I think to build a healthy culture, you have to intentionally avoid or opt out of those tidal pulls of culture at large.

Jonathan Hicken [00:07:05]: And I think part of the problem is that a lot of that conversation is happening online, and there’s a natural bias to what people are having the conversations online. People who work in the online sector, whether that’s social impact or not, are online talking about work culture. And that exists. I was in tech. I lived that and that’s real. And then that trickles down. And I think the problem is that then we start to believe that is the norm. And if we look at ourselves or we look at others and they’re not operating that way, you start to think that they’re slackers or that they’re not serious.

Eric Ressler [00:07:45]: Exactly. And to be clear, I agree that a lot of this is based on online discourse, but it’s also based on — I’ve seen this within organizations. I’ve fallen trapped to some of these things over the years and had to really intentionally sit back and reflect on, wait, why are we doing it this way? Why do we accept that we have to hustle? I mean, if you think about even the context of what an agency culture typically is and what our culture is, they’re wildly different. Largely because I was like, “No, dude, we’re not going to do it that way.” We’re not doing that. And so this is why I have a point of view around — no, I think culture is designed, because I very intentionally as a leader at Cosmic made some choices about, no, we’re not going to work 60-hour weeks as a standard just because we’re an agency and that’s what you’re supposed to do as an agency.

And it wasn’t because people came in and said, “Hey, I don’t want to work 60 hours.” A lot of the folks on our team have worked those jobs and expected to work that job. And we actually had to literally untrain that behavior for a number of our employees. We work a four-day work week, for example. So all of this to say, I’d like this conversation to lean into how might we imagine a healthier, more sustainable, and I would argue more effective culture for social impact organizations despite the challenges around funding, despite the challenges around capacity. Because I think sometimes we lean on those as real, but also over-leveraged excuses for why we don’t build healthier culture.

Jonathan Hicken [00:09:20]: Yeah. I don’t think those external constraints are an excuse to have a bad culture. I think those are simply constraints within which to build a great culture. And you can’t sacrifice the people in order to overcome some constraints that are out of your control. So you have to acknowledge your constraints. You have to acknowledge that maybe funding’s tight. And sure, that is something we want to overcome, but I’m not going to sacrifice my people to do that. And I think what you’re getting at is sometimes that is the trade-off that we either knowingly or unknowingly make.

Eric Ressler [00:09:55]: And I would go a step further and I would say that there are orgs and leaders who, I would say sometimes even intentionally or knowingly over-extract value from their staff and value the outputs more than the way they treat their staff. And there is a balance here, right? Because I think if we go too far where the staff becomes the almighty and they must be protected at all costs and that staff gets to drive everything, then you start to get into this place where there’s no vision or leadership for the organization either. So I think this comes down to balance for me. And that’s something that’s tricky, just frankly. And we’ve struggled with that balance at Cosmic over the years. I strongly believe I want to take care of my people and we do. And how do we do that and hold people accountable, set high standards for craft, set high standards for accountability and ownership of the work, all those kinds of things. That’s a tough tension to balance in my opinion.

Jonathan Hicken [00:10:55]: So let’s go through our two sort of different but possibly compatible, possibly not philosophies on how to do this. So I’ll start. For me, I went with people first. I have a sense of the kinds of people I want to work with. And the kinds of people that are going to do the work that we do the best. And so when I’m hiring, I’m looking for that before I’m looking for qualifications, before I’m looking for resume. I’m like, are the people going to show up in the way that I think collectively is going to create that culture, because it’s the driver?

Eric Ressler [00:11:35]: Yeah, we’re 100% aligned there. And we do the same thing in our hiring process.

Jonathan Hicken [00:11:40]: But we all say that, right? We all say that, but it obviously doesn’t always happen.

Eric Ressler [00:11:50]: So if I could reflect on that for a second, I think it’s sort of like dating at some level, where everyone’s going to be on their best behavior when you’re in that courtship phase to a degree. And even sometimes the intentions are right. And I think this maybe sometimes comes down to, well, what does it mean that we want to be collaborative? How does that actually work? So what I’ve learned in hiring and setting culture is getting very specific about what does it mean when we say collaboration? What does it mean when we say ownership? I’m just making these words up, by the way. Because I think sometimes we get lost in semantics. A potential employee may have their version of what collaboration means, and then they come and they step into the org. They’re like, “Whoa, this isn’t what I think of when I think of collaboration.” So there’s a misfit in practicality versus in the concept itself.

Jonathan Hicken [00:12:40]: I also think that you have to hire — there has to be somebody on your team, and that may be you, but ideally it’s not, someone who’s almost like the flag bearer of culture that carries that. And we did that at the Seymour Center. And this was somebody who owns the visitor experience, meaning delivering awesome human-to-human experiences in our building. But this was also someone that I knew right away. I was like, “Oh, they care about culture and they’re going to drive and carry that flag for culture for the whole staff, not just on the floor.” And I think that’s really important to have.

Eric Ressler [00:13:20]: I agree. And here’s where I think we are very aligned. I also don’t think that culture is something that is designed top-down, responsible only for the founder to set and uphold. In the best case of this, it is a co-created thing, but it needs to gel after a certain amount of time as a team so that when there is something happening that’s not aligned with culture, it sticks out like a sore thumb where it’s just like, whoa, whoa, that’s not how we do things here. And maybe that’s because of one person acting in a way that’s not culturally right or because of a decision the team makes or the entire team makes. When the culture is strong and defined, it becomes painfully obvious when something happens that’s not culturally aligned.

Jonathan Hicken [00:14:05]: For sure.

Eric Ressler [00:14:05]: And to riff on that even more, I accept and expect and invite people on my team to help shape the culture, to have ideas around the culture and how to uphold it in different ways. So there’s this tension there for me where it’s like, I do think some of it is shaped by leadership. And actually I think the part that’s most shaped by leadership is actions. So if you have a stated culture or a way of being, it can be performative if you say one thing, but then you actually act in a way that makes it clear that cultural norm or standard or idea is just paying lip service to the idea versus actually embodying the idea.

Jonathan Hicken [00:14:50]: Yeah. Kind of what we’re talking about, and I’d go as far as to say as the leader, what you’re kind of trying to do is you’re trying to define in-group, out-group, where the in-group are the people who behave this way. And the out-group, they don’t behave that way, which means they don’t belong in this work or within this team.

Eric Ressler [00:15:15]: Which they may be great for another team.

Jonathan Hicken [00:15:20]: Exactly. That’s not necessarily that they’re a bad person. And so I would say another decision, and this is probably arguably the hardest one, is making the decision to let somebody go who’s not a culture fit. And can you make that choice even if they’re producing results? When I was in tech, this was a tough one. The classic example of the Apple salesman who just was crushing it.

Eric Ressler [00:15:45]: By numbers.

Jonathan Hicken [00:15:45]: Yeah. By numbers, but the worst person to be around. And I thought the best SaaS companies were the ones who are like, “Hey, your results do not make up for the fact that you’re being an asshole, you’re out.” And that’s a really tough decision to make for a leader, to let somebody go who’s a high performer on paper, but is not a culture fit. But that is an action, Eric, to what you were saying, of demonstrating you as a leader that you are serious about this culture. That is a really powerful one when you’re defining that in-group, out-group.

Eric Ressler [00:16:25]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

So I want to share one other idea about how I think this happens, because what I don’t think usually happens is that there’s an idea around culture and then the leader or the org at large just kind of intentionally goes against that idea. I think what’s most common, what I’ve experienced at running Cosmic, is that we have a goal around what it means to work at Cosmic and how we show up and the way we want to do our work. And that there are short-term decisions that get made that run counter to that culture. And there’s sometimes even really good short-term justifications for why those decisions were made. But then because they run counter to the stated or the intended culture, they build and build and build, and then all of a sudden that becomes the culture. So for example, let me paint a picture of this in terms of something that we’ve struggled with at Cosmic that we’ve made some good progress on.

So one of the things I believe that’s very strong about our culture is we want everyone on the team to have ownership and agency in their work. And there’s a tension there in the dynamic because I’m our founder, but I’m also our creative director and we are a team. So by definition, we’re trying to do work together, and us working together is going to produce much better results than any one person doing their work in a silo, of course. And what has happened in the past is the team’s worked on something, they brought it to my desk. I look at it and I’m like, “Oh, I see exactly what the problem is here.” And my intuition in the early days of leadership and being a creative director was to present the solution to my team member. “Oh, this is a good start, team member, but here’s why it’s not working and here’s how you solve it.”

And what I’ve learned over the years doing this is that that is not a good leadership style or even a good creative direction style. A better approach is to say, “Hey, here are the things that are working. Here are the things that I think are missing the mark, and here’s why. How might you solve that?” And again, putting the agency and the responsibility and the ownership back on the team member in a constructive way, not a like, “Oh, I don’t have time for this. I don’t want to deal with it.” It’s like, “I want to help grow you as a professional.” But the trap is, “Oh, and this is due in two days, and we can either solve it by me giving the solution and be on time. Or I can say, take it back to the drawing board and we have to push that deliverable back.”

So in the short term, it’s very tempting to say, “Okay, I’m going to help you solve this. I’m going to roll up my sleeves and get in there.” But that doesn’t actually help the team member grow. So we’ve had to build in more buffer, especially for newer team members or new deliverables that we don’t have as standardized, or even just straight up sometimes like, “Hey, didn’t hit it the first time on the first attempt.” And so what I’ve noticed is that when I wasn’t as diligent about that, it started to create this culture of like, “Oh, nothing can go out the door without Eric seeing it first.” Or, “Oh, well, I’m not going to take this as far because I don’t want to bring it to Eric and then have him tell me to do it a different way and I’ve spent a bunch of hours on it.”

So it’s a tension there that we’ve dealt with, but I use it as an example because I think that’s how culture erodes.

Jonathan Hicken [00:20:35]: All right, I have two ideas for you on that example. One is, can you tell them to bring you back an idea in short order? Like, “Hey, think about this problem and bring me your idea in an hour.” And it’s just like you keep the pace, but you give them a chance to think.

Eric Ressler [00:20:55]: Yes.

Jonathan Hicken [00:20:55]: And if you don’t have that luxury of time, then can you name what happened shortly after the project shipped? Where it’s like, “Hey, we got that out the door. The client’s happy. That’s great. We got where we needed to go. I didn’t like that I kind of just gave you the solution there. How can we do that differently next time?” So it’s quickly naming what went wrong shortly after. I’m just spitballing, right?

Eric Ressler [00:21:20]: Those are great. And actually some of the things that I’ve done over the years and learned how to do better. And one of the things I learned early on is like, oh, we need checkpoints earlier in the process so that we can make sure we’re strategically aligned before a designer or a writer or a strategist or a developer goes out and burns 20 hours on a project for me to come back and realize like, oh, we had two very different ideas around what we’re trying to do here. And again, I want to be clear, I’m not even saying I always am the right fit to solve these problems. Now, I’ve been doing this for a long time, so I’ve done enough cycles to have an intuition about this where I think my superpower I have developed over the years is I’m a very good, deep listener at this point.

So I’ve developed a skill of being really good at understanding what clients are looking for and knowing if what we’re coming up with is truly hearing them and truly solving for what I’m hearing from them. And my team is really good at that too. But sometimes I have a spidey sense almost that I’m like, “Hey, this is cool. This is a good solution.” But I know exactly what the client’s going to say if we bring this to them. And I’m not always right, but I will say that’s probably my biggest superpower as a leader and a creative director.

Jonathan Hicken [00:22:40]: Yeah. And that’s why you have the role that you have.

Eric Ressler [00:22:40]: Right. And again, oftentimes my teammates will come up with better solutions to that problem than I ever would. But that’s a skill that — so what I’m sharing this for is like, yes, what I’ve realized is, okay, so those are some of the constraints. How do we make sure not to do these short-term things that — it’s not even really fixing the problem or even delivering better work at times, but it’s easy to fall into those traps. And I think that’s how culture starts to erode. And for a social impact org, it might be like, “Well, the grant’s due, so we’re just going to roll up our sleeves and do it.” Or sometimes it’s even like, “Hey, this isn’t a value-aligned funder, but if I don’t get this grant, I’m going to have to lay some people off.” And this is how culture starts to erode, just as some off-the-cuff examples for social impact orgs.

Jonathan Hicken [00:23:30]: Right. Where you start with, “Hey, we’re going to have to burn the midnight oil on this one grant,” and then it’s the next grant, and then it’s the next grant. And all of a sudden now you’ve set this expectation, not just with the person who’s staying up late, but for everybody else who’s seeing it, that success looks like staying up super late on grants. And so I better do the same because that’s what it looks like to fit in. That’s that in-group, out-group thing again.

Eric Ressler [00:23:50]: And what I would say is the point I’m trying to make here is that culture is built by the consistent decisions and actions that you make as an org, not by your value statement or your posters, to your point. And I think this is where you start to see sometimes even staff roll their eyes when you hear people talking about culture. It’s like, well, culture is really about, what are the choices that we make consistently over and over and over and over again? And sometimes you’re going to have to burn that midnight oil. Don’t get me wrong. Last year, for example, as I’ve shared on the show before, was a brutal year for us because of just the state of play in the sector at large. And we had to do some things that were to a degree counter to some of the culture.

So for example, we often had to work more than four days a week, which is part of our culture. We had to take on some projects that maybe weren’t as good of a fit for where we’re trying to go. And we did that with clear eyes, but this year, a lot of my work has been unraveling some of those new norms, mostly even for myself around how to build a sustainable and healthy way of working for me. And so I think it’s just something to keep in mind in terms of, well, how do we build stronger, more healthy, more sustainable cultures? To me, two things: question the norms. Do we have to do it this way just because that’s how everyone else does it? And how do we actually show up day after day, choice after choice?

Jonathan Hicken [00:25:15]: Because I think that culture is emergent from the collection of people, and I agree, to the sum of your decisions. I think there’s a couple of really important things that any culture, a positive culture, no matter what culture that is, because there’s many different flavors of it, needs to have in place. One is the right people. I started with that. The second is a set of tools that helps every single individual understand whether or not they are making the right decisions or the decisions in the style that match the culture. Something that they can self-check on and that they can hold others accountable to doing the same. So to your example of the executive director or founder or whatever stepping out of line, someone should be able to call you on that and be able to name that. And if they can’t, or that trust doesn’t exist, that’s a whole problem.

That’s a whole other independent cultural problem that nobody can actually call you on that. So just a couple of examples of things that I do at Seymour Center, some guardrails, so to speak. One is we define what success looks like numerically. So quantitatively, I think that’s an important part. Am I doing my job and am I doing it successfully? And when I show up to work, am I walking away being like, okay, I’m doing the kind of work that’s going to get results. We need that scorecard. I believe that. Everybody needs that. I think the other thing, and we have recently started calling it the Seymour Way rather than core values. Because one thing we’ve learned is I can’t actually tell somebody what their values are. We all bring our own values to the table. What I can say is, “Hey, this is how we do it at Seymour Center.” And so we call it the Seymour Center Way.

And these are five sort of behaviors. One of them is make it right. One of them is experiment, actually. One of them is better together. So these are like, “This is how we do work.” And I’ve mapped all of those elements to real work and real decisions that people on the team are making every day. For example, a visitor walks in, what does it mean when we are going to make it right versus when we don’t make it right? And so if you’re on the floor and you work the floor, here’s what that looks like and here’s that difference. So when you’re in that exact situation, you have the tool to make the choice, which you were describing in aggregate. When those things all add up, now we have created collectively the Seymour Way. So we’ve defined those things and made it really, really specific. So those are just two examples of tools that I’ve given my team to make sure that we are collectively doing it.

Eric Ressler [00:28:05]: Yeah. I love that point, which is you have to get out of the abstract here. And so this is, again, why I think that it comes through modeling a lot of times. And that doesn’t mean only leadership modeling. The whole team models to the rest of the team what culture is. And you say the Seymour Way. I think that’s a great way of, in two words, describing culture. This is how we do things here. One thing I’ve also learned is that a lot of it comes down to just clear, respectful, but clear communication of just like, “Hey, I expect this from you because X, Y, Z. Because this is our culture, because I want you to learn,” whatever the reason is. “I’m here to support you, but I expect you to own this and take it home.” Because otherwise you can start to build this culture of resentment or vagueness where I’m just like, “Is this my job or not? Should I be doing this?”

As a team member, even as a leader sometimes I’m like, “Is this my role? Is this what I should be doing? Should I be coming in and firefighting on this thing? Or should I say, hey team, I trust you fully to take this over the finish line. And by the way, if it doesn’t go well, I’m here to support you.” So some of this I really do think comes down to the term being psychological safety. Team members, and really this goes from the bottom up, feeling like they can fail and be supported by the rest of the team. Because I think a lot of times culture gets really bad when people are afraid to fail or afraid to step out of their bounds or they’re going to be blamed for something. Or at times it might even be just like confusion. Am I the right person to do this? Should I do this? Am I allowed to do this? So I think a lot of it comes down to just clarity of communication and safety.

Jonathan Hicken [00:29:50]: Yeah, you’re talking about, I think, trust, fundamentally speaking. At least that’s how I interpret it. And there’s this great book, Five Dysfunctions of a Team. And one of the fundamental dysfunctions is a lack of trust. And I think everything falls apart if that doesn’t exist. And what you have just described, I think, is a scenario or a set of compounding decisions that would create a lack of trust. And I think at the beginning I talked about culture’s not something that’s stagnant. You can’t say it’s done. And I think part of that, even within a healthy culture, there are ebbs and flows.

Eric Ressler [00:30:30]: Of course.

Jonathan Hicken [00:30:30]: In terms of what is required of the team at that moment. And the easiest way to put it is there are times when we need to grind, and there are times when it is appropriate to relax. And in fact, it’s healthy too. And in those moments of grinding, as leaders, we need to do two things. We need to build a culture of trust that people know that we will return to that moment of relaxation. And I can trust that we will get there again. Otherwise, there’s this fear that we’re going to be there forever and we’re going to grind there forever. So you as a leader need to know and recognize when you are in these different seasons and be able to build a team that trusts you to get back to those periods of peace or those periods of homeostasis or whatever you want to call it, right?

Eric Ressler [00:31:25]: Yeah, that’s a great point. And I think to reflect on that, I’d love to get your take on this. When we are in a point of grinding that’s team-wide — now look, everyone on my team, there’s times where they got to grind, and there’s times where they get to rest and things are a little more chill just depending on the client work we have, where we are on the project, all that. But last year was a grind year. And I made a really intentional choice. And it’s like, I don’t know that I could even not do this, but anytime I’m asking the whole team to grind, I feel a moral obligation to grind just as hard, if not harder, than the rest of the team. Because I think it’s really unfair in my opinion to be a leader and just push your team to grind while you’re not. You’re like, “Well, this is a you-grind problem. And I’m sitting up here in my lofty golden chair, just kind of reaping the benefits and extracting value from you.” So to me, especially for a small team, if you’re a leader and you’re asking your team to grind because of whatever reason, you got to roll up your sleeves right there with them.

Jonathan Hicken [00:32:25]: That’s a slippery slope because your season may not always match the season of people on your team. And so the slippery slope is you actually stay yourself in grind all the time because you need to grind. If you’re grinding when they’re grinding, but then you need to grind when you need to grind, and you’re always grinding, right? And then you burn out. So a culture of trust is one where the team could see, oh, Eric needs a break and he’s taking a break and I got his back.

Eric Ressler [00:32:50]: Yeah, fair.

Jonathan Hicken [00:32:55]: So yeah, yes, the team needs to see you grind.

Eric Ressler [00:32:55]: Yeah.

Jonathan Hicken [00:32:55]: Do they need to see you grind at the exact same time?

Eric Ressler [00:33:00]: Yeah.

Jonathan Hicken [00:33:00]: No.

Eric Ressler [00:33:00]: I think that’s a really fair point. And I think that that is frankly a trap that I fall into because kind of one way or another, I’m always in some form of grind. Because if we’re busy, I’m grinding. If we’re not busy, I’m grinding to get busy. And so that’s where I say I’ve had to build in some very intentional structures, boundaries, lifestyle around how do I make sure to stay healthy for Eric? Because the thing I’ve definitely learned is when I’m not happy and healthy, the whole team’s not happy and healthy, especially being a small agency. So Jonathan, I think this has been a good primer into some of these things. I hope this is inspiring. I know this is top of mind for a lot of teams right now, and it always has been, but I think especially right now, teams are trying to figure out how do we settle into this new chapter of either our org or the sector at large?

And I think what I’m hoping is that we could collectively reimagine healthier ways of doing this work long-term, especially in the social impact sector, but just generally, because I think especially with AI coming in and all this stuff, the trap is just going to get deeper and deeper to just do more and more and more and more with less and less and less. And that’s just not going to work long term.

Jonathan Hicken [00:34:15]: No, it’s not. So I would say leave folks with this. Hire the people who contribute to your culture, fire the people who detract from it, and give people the guardrails and decision-making tools so that that aggregate culture emerges.

Eric Ressler [00:34:30]: All right, Jonathan, thanks for riffing on this one.

Jonathan Hicken [00:34:30]: That was fun. Thanks, Eric.

Eric Ressler [00:34:35]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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There are two camps forming around AI in the social impact space. One says boycott it. The other says you’re already behind. And most people in the sector are stuck in the middle, exhausted.

The people doing the hardest work in the world keep getting told they’re not moving fast enough. Or that touching this technology at all betrays their values.

Meanwhile, the biggest decisions about AI are being made without us. By labs. By shareholders. By governments. And the sector that exists to challenge those structures is barely in the room.

So what would it take to step in? To hold space for the skeptics and the builders at the same table. To use AI as an imagination tool, the way the best of this technology was always promised.

To explore that, I wanted to talk with two people who live in that middle ground on purpose. Kaz McGrath and Stephen Silveira run a company called PLAI, for Purpose-Led AI. They’ve spent their careers inside the nonprofit sector, and they don’t show up as AI evangelists. They show up as guides.

Their approach starts with play. Real play. It’s what gets a guarded room to loosen up and talk honestly. Then they ask the question most people skip: what actually furthers your mission?

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Episode Highlights:

[00:01:00] Meet PLAI and the “you don’t have to use it for that” philosophy
[00:04:30] “You are behind” — the exhausting message the sector keeps hearing
[00:08:00] What if nonprofit professionals became the builders?
[00:09:00] The roles we all play in change: trailblazers, hospice workers, and the bridge between
[00:12:00] From ethics-first to “speed run it” — how the AI narrative shifted
[00:15:30] Tracking endangered species in the Amazon, led by Indigenous elders
[00:19:00] The one filter for every AI decision: does it further your mission?
[00:23:30] Imagining the best case, and the moment it gets emotional
[00:26:30] The environmental truth nobody mentions: your impact depends on where you live [00:35:30] Decisions are being made for us, not with us
[00:36:30] Play as a serious intervention
[00:40:30] Why mindset matters more than mastering the tool

Notable Quotes:

[00:04:30]: “People in this sector are brilliant. The most passionate, dedicated, giving people that I’ve ever met. They just need the right teacher, the right guide to help them be also excellent at AI.” Kaz McGrath

[00:08:00]: “These amazing people we’re talking about are closest to the actual problems that need to be solved. What an exciting opportunity that they can now be builders and solve some of these problems directly.” Stephen Silveira

[00:19:10]: “There’s a billion things you can do with AI. We try to center folks on: yeah, but what’s actually going to help your mission? Because anything else might just create more busy work for you.” Stephen Silveira

[00:26:10]: “People are using AI to be that silver bullet. They want this future we’re trying to describe, and they want to say AI is the thing.” Stephen Silveira

[00:35:55]: “These decisions are being made for us, not with us. For us, not without us. And it’s in that space, I think, we need to, as a sector, step up into the role we can play.” Kaz McGrath

[00:38:50]: “We’re not going to go to a five-year-old kid and present a PowerPoint on learning how to share. We’re going to play. And I think sometimes adults just need to admit that we’re all still kids.” Kaz McGrath

Resources & Links:

• Purpose Led AI (PLAI) — Kaz McGrath and Stephen Silveira’s organization, helping nonprofits move from AI-curious to AI-capable

• The Playground — PLAI’s newly launched always-on live AI experiences for the sector.

• Conor Grennan’s AI Mindset — the mindset-shift framework Kaz references

• Berkana Institute — Two Loops Model — Margaret Wheatley and Deborah Frieze’s model of change roles (trailblazers, hospice workers)

• New York Climate Week — where Kaz encountered the Amazon conservation project

• AI for Climate and Conservation Solutions

• Indigenous-led Biodiversity Credits and payment

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:15]: So Kaz and Stephen, welcome to Designing Tomorrow. Thank you so much for joining me here today. You guys are called PLAI, P-L-A-I, purpose-led AI. And I’m recognizing that for our listeners who don’t have as much context around you and PLAI, just tell us a little bit more about the work you’ve been doing and the work you are excited to be doing, who you’re becoming as an organization, and what you see as an opportunity for the sector right now with regards to AI, but also just with regards to all these different ways of working and transforming the sector.

Kaz McGrath [00:01:45]: Well, I’m going to start with what we’re so excited to be doing, which to me is we’re just so excited to show and make people feel what is possible now in this space. And at the same time, be a team who knows our stuff, who’ve worked in the nonprofit sector our whole lives, who’ve been there, and can guide people into ensuring that that’s aligned to their values, to their principles, to what they care about in the world, what they care about for the environment and their future. So for AI, that looks like guiding leaders and teams in designing epic, fun, incredible new solutions, and then also being able to set up those boundaries of what we never want to do. The craft — we’ve worked with journalists and storytellers and fundraisers, and their shoulders drop when we remind them, you don’t have to use it for any of that stuff. Keep writing stories, keep having those relationships. Don’t let it influence your craft in what you see. And I think that unlocks a lot of possibilities of AI in the space.

Stephen Silveira [00:03:00]: Another aspect — regardless of the product or the way we’re working with clients, there’s that aspect, and there’s also the aspect of we start talking about AI and we’re like, “All right, what do you want to do? What’s your use case? Okay, what’s the workflow?” And those are actually the chunkier bits that we end up helping people design. Often people are like, “I don’t know, I’ve never mapped a workflow before.” And so you need to be able to do that to decide where AI fits, where the human fits. So much of what we’re talking about with bringing that humanness or deciding where to put your boundaries depends on knowing what the workflow is. And I think we often run against people who are brilliant, have all of that, but they’ve just never mapped it out in a certain way or done that design process. And so a lot of what we teach or help people go through is that. AI is the topic, but it could be another topic and it’d be a very similar thing. And the aha moments we see in people — sometimes it’s AI being like, “Oh, I don’t have to use it for my writing. Thank God.” And sometimes it’s like, “Oh, that’s interesting. I’ve never thought about who else is in this workflow with me and what they would think about this.”

Kaz McGrath [00:04:05]: I’m feeling quite fatigued at the moment by a lot of the messaging around the sector in social impact, and especially in nonprofits, with this — you are behind, you don’t know enough, you have to do more. We have to add, we have to continue to be in that frantic rat race. And what we’ve seen is the opposite, which is people in this sector are brilliant. The most passionate, dedicated, giving people that I’ve ever met. That’s why I love working in this sector. And they just need the right teacher, the right guide to help them be also excellent at AI. And that doesn’t mean excellent at using it for everything, but it’s about getting teams and leaders to that place where they feel equipped to make really confident decisions that feel aligned to how they want to tell stories, how they want to connect, so they can go and create an amazing new app that changes how they can engage in their mission or in their work. And then also have boundaries, feeling like we’re not getting carried away with everything else going on that we feel is against what we stand for.

Eric Ressler [00:05:20]: I want to acknowledge and lift up part of that, which is what you said around these are some of the most brilliant, passionate, talented people. And frankly, our sector to me in the public discourse sometimes feels like a second-class citizen. Like, oh, isn’t that cute you work for a nonprofit? Or, oh, that’s great you do this kind of give-back work. What did you do in your serious career before doing that? And this is all wrapped up in a catch-22 on the scarcity mindset, because frankly the sector at large does not have enough resources to do the work, because the work is the hardest work in the world. And so there’s almost no amount of resources that would be sufficient, but clearly what we have is generally — not speaking sector-wide here — not enough. So I want to elevate that.

And then I want to ask about — let’s get into the AI thing a little bit, because we’ve touched on it on our show, but we haven’t had an opportunity to go really deep. If there’s ever a complex issue that should not be a black and white issue, it’s probably AI. So AI is, in my mind — and I want to hear how you guys think about this — possibly not proven yet, but possibly the single most transformative technology ever invented for humankind. And at the same time, there are huge ethical and maybe even spiritual concerns around how it’s being done, how it’s been done, who’s leading it. And what I’m noticing is that there are these very polarizing and different camps of thought. I see people in the social impact space who are outright essentially boycotting AI. And I think they have some valid criticisms around the extraction and how these models were built and the climate impacts and some of those kinds of things. And then you have the AI bros who are just like, yeah, you’re behind already if you don’t have a 26-orchestrated agentic workflow writing your fundraising copy for you. Obviously somewhere in the middle is likely where we are and where we’re going, but how do you guys think about this moment and balance all of that in a sector that is rightfully there to challenge some of these structures in society? And there are, in my opinion, some things about AI in general and how AI is being done that are worth criticism.

Stephen Silveira [00:07:50]: 100%. We sometimes have to convince people we’re not those AI bros that are just like, just do everything with it, you’re so behind. And we really believe that these amazing people we’re talking about are closest to the actual problems that need to be solved. So for me, what an exciting opportunity that they can now be builders and solve some of these problems directly without having to depend on this infrastructure of agencies and consultants and everything all the time. But then there’s this worry that it’ll be like most other technologies where it won’t be available to them. So where’s this gap, and who’s able to use the really cool things with this technology? Right now so much — tokens are free and easy — and will that change? Because it’s really exciting to think of nonprofit professionals being the builders and being able to like, let me mock this up real quick, or let me put that up on my own without having to go through all this red tape first.

Kaz McGrath [00:08:40]: Listening to you speak around that, I immediately picture those people that we work with and what this moment feels like for them. And sometimes it can be frustrating when there are opinions that feel not grounded on what the technology is and can do and is set up to be. But I really think about, for people in the sector right now, it is — and for all of us, it is — exciting, it’s scary, it’s nerve-wracking. It pushes on a sense of identity and of the future that I haven’t seen us in my lifetime meet before, other than the start of massive shifts in COVID. But this feels somewhat bigger than that. And in those moments, all of us are needed. There’s this incredible model of disruptive, huge change by Deborah Frieze that talks about the different roles when we go through change — the trailblazers, the hospice workers, the different elements of bringing everyone along. And there are going to be some people pushing those new possibilities. And there are going to be some people trying at all costs to protect what has come and gone. And I like to remind people that we are all needed. In a team, we need people who are asking the questions and pushing harder and saying, “But what are we not thinking about? What is unsafe?” And we also need those who are sparking new possibilities. And I think for us, we see our role as sitting as the bridge between that — to be able to see those new possibilities and push the hopefulness forward, but also fight against the worst of it. It’s like, how might we make the best of AI and use that for ourselves, our lives, our missions, and how can we fight the worst? And what we’re seeing a little bit of is those conversations not including the other.

And I think we need both. It’s back to your point on getting away from binaries. And we can achieve that. And I would love, in the sector, from those who are skeptics and who are saying we need to ban AI — I would love them to talk about what AI means for people living with a disability, what it means for someone who could communicate in language that they previously couldn’t access, translation. I would love them to see my mom, who’s got a chronic health condition, whose life has changed because of what AI has done for research in that space. And then vice versa, I would love those people who are pushing the possibilities and saying, “We need to do this, this is the next big thing,” to sit with their colleagues who are scared about this, who think it’s a terrible idea, and say, “Tell me why. Tell me more. I want to listen to that.” And that’s the power of those conversations, and why facilitation and gathering and why design is so important — because there isn’t one answer. We need to sit together and then we need to design our way forward of what comes next.

Eric Ressler [00:11:55]: It’s funny, because I feel like when this started to become seriously mainstream — which to me was essentially when ChatGPT first launched, even before it became public-public, but that’s when it was like, okay, this is a breakthrough, this is coming — it seemed to me like there were a lot more of those conversations happening around the ethics of AI, even from the AI labs and safety. And then there was a moment where it seemed to be — and tell me your guys’ point of view on this — from what I saw is like, “Oh, well, we can’t actually have guardrails because China’s not going to. So now we’re just going to speed run this thing.” And so early on, at least the messaging and the marketing from the major labs and the providers, and the people within those teams who I genuinely believe are just super excited builders and thinkers about this — if you just separate the economics and the shareholder primacy from this, the people in these labs are deep thinkers, and they’re geeks, and they’re excited about this and they see the potential. And there was a lot more talk about the social impact potential around, yes, drug research, medical research. And then all of a sudden it seemed to be like, “Oh wait, we’re going to solve coding.” And to a degree, even you see folks from Anthropic saying, “We’ve solved coding.” But then you look at their uptime status page and you’re like, “Maybe not quite yet.”

So what I would question for us in this room and for the sector is how do we — like you said, I’m inspired by the way you just described. We need to get everyone into the room and hold space for all of those points of view. I want people who are out there protesting AI. We need those people who are holding these companies and governments accountable to the extractive nature of what’s happening, the climate impacts of what’s happening, which I think are much more nuanced than are being described, based on my research at least. So I guess my question to you all, in terms of how you think about it, is: now we have this opportunity, especially you two and your company, to prove out that this does have transformative potential for creating positive social change beyond just writing automated funder email sequences. Great, it might be able to do that, but how can we use it as an imagination tool alongside of that?

Stephen Silveira [00:14:25]: I love that. That’s a lot of the framing. Sometimes our most powerful workshops are holding space, like you said, for people to talk through that. And then once they’re able to get some empathy, then those exciting possibilities come up. But if you don’t start with that, they don’t come. I like to think we try to do that at a meta level with the work and the things that we offer. And in each individual intervention — workshop, lab, immersion, whatever we do — we’re going to start with holding that space. And we’re going to tell the skeptics, we need you. Please speak up. Sometimes, like you said, when AI was new, people were talking and more discussive, but then people start picking a side, and you either hate it or you love it. And people start workshops like that sometimes like, oh, Jerry’s a skeptic, so don’t bring him. It’s like, no, we need Jerry. We need Jerry in there right alongside the person that’s been using Claude on his own in secret with nobody knowing.

Kaz McGrath [00:15:20]: And I think it’s helping people towards their own imagination. What we’ve seen often in these rooms is, because of the push towards productivity and efficiency and saving time, the brand image of AI was that — or creating funny memes, or whatever the ChatGPT image trend of the moment was, the order on an airplane or something. And what I think is really important for our sector is: yes, of course we have to do that. I don’t know anyone in our sector who doesn’t have five other roles that they’re playing that they could 100% save time and automate and use AI on, tiny models that don’t have much of an impact on the environment. But the more powerful thing we need to be doing is finding and telling and imagining those stories of the deeper work. On a small example, we’re meeting in a room with 50 of our colleagues, and by the end of a two-hour workshop, seven people got to talk. And there’s so many ideas there. There’s so much passion and perspective and context that we can collect and sense-make and process together, to not remove that connection but to lead us further towards it.

I was at New York Climate Week, and there was — I’ll find the name and put it in the podcast notes, I can’t remember the organization’s name — but they’re using AI to track endangered species in the Amazon in real time to inform decision-making, and do it in a way that supports indigenous employment, protection of the rainforest. And I want to be telling those stories to people, because what they were doing was never otherwise possible, but they were doing it fully in connection to the elders there and to how that community wants to operate. They led it. It wasn’t led by someone bringing it in. And that was long before ChatGPT — this program existed years and years ago. So one of the things that will break this down is people actually starting with learning. You don’t have to enter it by doing. We can learn and explore what is possible and not just talk about AI as a chat-based interface over a gen AI model. Talk about the possibilities of this and lead people to things that will create further connection, that will allow complexity thinking, that will allow us to process a billion data points rapidly so we can have new approaches and new answers to things.

And the final bit — we talk a lot about bias in AI. The thing that made me smile about bias is: there are definitely some organizations and institutions that have done deep, incredible, sustainable work in the area of bias. There is a lot that haven’t. And there is a lot of one or two humans, or a small team of humans, that make decisions influenced by their background. I’m part of the queer community, but I’m white. I went to a private school. I worked for an NGO. I can never make decisions in that space without being biased. It doesn’t matter how much training I do. So sometimes it is an important mirror for that as well, in terms of when do we need to acknowledge that, hey, that actually is a better solution than how we would approach it. And how do we have the right discernment and decision-making so that isn’t removing the deeply human connected work that we do?

Stephen Silveira [00:19:05]: Just real quick, to pull out of that what we didn’t quite phrase succinctly: it has to be focused on furthering your mission. There’s a billion things you can do with AI. And so we try to center folks on, yeah, but what’s actually going to help your mission? Because anything else might just create more busy work for you. There’s so many things you can do, and if it’s not mission-centric, then a lot of these things start to matter more about how much resources they’re using. But that rainforest example — they’re using it for this specific purpose of their mission, which they believe is bigger than these other things. So you could tell someone’s had that conversation. And I don’t think people are having that enough. They’re saying anything is bad, versus like, okay, but what can you do to actually further the reason you exist in the first place?

Eric Ressler [00:19:45]: I think this is the reason why narrative change is so important, especially on this topic, because I do think right now the narrative is really bad for AI. The narrative is, first of all, in a practical way, you load up a chatbot and you ask AI to do your work for you. That’s the framing I think most people have. And because of that, if you’ve had an AI experience where you’ve tried to use AI without the proper context or the proper training or the proper understanding, it’s going to produce bad work. It’s going to produce inaccurate work. It’s going to hallucinate, whatever it is. And the models are getting better at all of that just inherently, but still, I think a lot of people have tinkered and written it off without having the right conditions to truly assess it. Not to mention that it’s changing every week.

So there’s that part of the narrative that I think needs to be fixed around what does it mean to use AI for social impact at large? And it’s not an exclusively chat-based individual worker system. That’s not how it should be thought of or imagined. And then there’s the broader narrative around AI is here to replace knowledge workers and eventually more than knowledge workers — this displacement theory of AI, which we need to be taking seriously, because there are some real, already some data to show that that could be happening. Then there’s a counter-narrative around companies starting to look at the cost-benefit of token costs versus paying humans to do the work. So all of that’s messy. And so if we were to instead — what’s the narrative that should be out there for social impact? If we imagine together right here at this table, 10 years from now, 20 years from now, this is a transformative technology and everything goes wildly great and positively. Let’s pretend the world doesn’t suck and everything—

Kaz McGrath [00:21:50]: That’d be really nice.

Eric Ressler [00:21:55]: But what is that? What’s that imaginative state? Because I think there’s so much in this space where we suck at imagination collectively. Not all of us, not individually — there’s counter-examples — but we spend a lot of time talking about problems in this space and the injustices. And that’s true. We need to do that. And that’s happening for AI. But what if we were to imagine the best case of this? What would that look like, and what would that unlock for the sector?

Stephen Silveira [00:22:20]: I’d love seeing — back to people in the sector tend to be so close to the problems — having that be celebrated, because there’s a human, real-person aspect to that that you can’t really replace. So seeing the nonprofit industry looked at as the experts, and seeing them maybe, maybe not, being the builders with the AI tools, but regardless, people that build the tools or orchestrate things would need them because they have the relationships, they have the understanding of the issues. There’s clearly the burnout — everybody, honestly — but people in the sector could be working 20-hour weeks and be getting paid more because the impact’s there for it. I think that’s a dream that’s very there for us if we can control the capitalism of the technology.

Kaz McGrath [00:23:05]: Oh, I love that dream. But also — I’ve just noticed in my body, trying to imagine that and holding that at the same time as what we’re seeing going on is physically hard for me in this space. And that is what comes up for people. So to me, I envision bush walks with my nephews. I envision surfing and having time to sit by a campfire and tell stories. I envision being able to have help on the tasks that I struggle with, and communicate more effectively. And when we are coming together to design new solutions in our nonprofits, it allows us to have the individual thrive in that’s made possible, and kind of solve the busy work for us, but also help us at the things we’re not good at. It would allow us to collaborate across INGOs in multiple different languages. It supports inclusion and people living with a disability being able to break down those walls and those barriers that have created an alternate experience for them that keeps those spaces away. It means medical research — it means I could... I didn’t think I was going to get emotional in this podcast, but I just did.

Stephen Silveira [00:24:25]: Eric said it’s okay to cry on this podcast.

Kaz McGrath [00:24:30]: Exactly. It would mean that medical breakthroughs mean my mom can actually come for a walk with me longer than 20 minutes on that beach. And holding that is such a beautiful thing. But I also think it’s only one piece of that imaginative... there we go. I wonder how in focus the tears are. I think the way we get there is so much more about who we are and our identity and how we make decisions, and not about AI. I think AI is the thing of the moment right now. But if we ignored everything that was developed in the future and nonprofits only used ChatGPT 3.5 from November 2022 — I ran workshops on this stuff — if all we did was that, with that model, and we did it in an intentional way and we prioritized our work and we reimagined what that looked like, we would have incredible progress in the sector. And now we have this suite and menu of possibilities and of tech, and everyone wants multi-agent teams and all this stuff. Amazing. We can show you how to do that. But we can’t get there without better collaboration with our colleagues, without healthier cultures, without having deeper questions about burnout and about why are we here in this sector, and without reimagining things with AI, reimagining them without AI. So I love the vision of that future, but I also think it’s so far beyond AI.

Stephen Silveira [00:26:05]: Yeah, it’s not AI. Because I think people are using AI to be that silver bullet. They want this future we’re trying to describe, and they want to say AI is the thing. That’s what we walk into workshops with clients with all the time. They’re like, just give me the advanced analytics tool. It’s like, wait, wait — half your team does not want to touch the tool. You have to figure that out first before you get on the advanced analytics tool, which, by the way, your data’s not ready for.

Kaz McGrath [00:26:35]: 100%. And it connects to all these side conversations we have with clients — which are great, which we love, the side conversations. We love them, but we never expect them. One of them is the environment. And something that shocks people is the bigger impact of your AI usage is just where you live. There are places around the world in which the energy mix and the impact of these things is completely different. And there is net-zero impact in certain types of AI and in certain locations. And then in other places around the world, just because of where that comes from, it’s 80 times worse, 200 times worse. So we want people to have those conversations and be able to meet and gather and talk about the reality of them without simplifying and scrolling over these things.

Eric Ressler [00:27:30]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring your ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Eric Ressler [00:28:20]: On the environmental front, I think a lot of the conversations around the environmental impacts have shifted towards data center creation. And the tragedy of this to me is that — again, I want the counterpoint to this, I want people protesting and questioning these things — but I also want us to develop more of a bountiful mindset around: isn’t this just one more reason why we should be accelerating clean energy? Why are we thinking in a constraint-driven way around energy when we basically have the potential for limitless energy in the world with the tech that we have right now? We just need the cultural will and the political will to make it happen, which is easier to say than to do.

But all that to say, what I’m picking up on is this — and this is where I go too — sort of how you shared your vision of this, Kaz: the medical breakthroughs, the potential for human progress. And also, to me, in the utopian sense and what was promised early on, this reclaiming of the human spirit and a way for most workers who are not billionaires — and even billionaires are working like crazy, because maybe you have a personality defect or something, I’m not sure — but I’d love to be able to accomplish as much as I do right now and work half as much and have more time to just be a human. Not that working isn’t part of humanity, but I think a lot of people in our sector feel like there’s not enough space and time. And that space and time is where imaginative thinking happens. It’s where solutions are born from. Even the simple example of a shower. We run a four-day week at Cosmic and have for over a decade, because creative thinking happens when you’re not putting pen to paper on the project all the time. And our creativity and that spirit of creative problem-solving — we’re in the business of that at Cosmic in one way or another, whether we’re doing strategy work or branding work or whatever.

And so if we don’t have space — and I’m speaking personally here for me and my team, but I see a corollary in the social impact space regardless of whether you’re in fundraising or you’re an executive — we need to go out and live our lives too. And unfortunately, a lot of people aren’t doing that to the extent that they would like to. And now we have this new technology that promises that, but you can also get spun up — and I’ve done it — of like, well, I just need to hit this one more time and get this AI workflow set up. So it can fill the space too. So how do we ensure... And I think it needs to be grassroots. I don’t think this is going to be some kind of globally or government-sparked worker protection thing. Even if that happens, it’s going to be because a bunch of badass people came together and demanded it. So can we create space in the sector to be critical and optimistic about this technology? And can we take a moment to think about redesigning our lives in the process, in kind of a true design-thinking way?

Kaz McGrath [00:31:35]: I just want to pull on a thread at the start, which is: the technology already exists to solve a lot of this stuff. My older brother Chris ran a solar startup, and it was incredible to watch that grow over the last seven to 10 years and learn deeply about what sustainability and the energy mix looks like around the world, and what already exists that we’re not using. And I think that’s the reality. We’re not hitting Paris. We’re seeing governments and industries go backwards. We’re seeing terrible decision-making, lack of accountability, divisiveness. And at the same time, in the political landscape, we’re seeing people like Mamdani give us the hope to gather again — what is this meant to look like? What is connecting and accountability in politics meant to look like? And when we talk about AI and the future and what do we need from governments and all these things, I think gathering and being able to have more time with our friends and our families isn’t just a hopefulness, it is survival as our world continues to change. Living in Australia, you feel every day the impacts of the climate crisis. And people all over the Pacific, communities around the world, already are feeling this. So if we don’t do that well, if we don’t find ways to gather, to strengthen our local communities, to strengthen our nonprofit sector, that is the heartbeat and the foundation of so many of our communities and our structures — we have to do that, because what is coming is going to get worse in that space. And when we then interweave AI into it, there is everything from, “Hey, the climate thing is already done, we need to be talking about existentialism and how do we survive through the collapse of our climate,” and people saying, “Well, therefore throw everything at AI, no matter how much energy, no matter how many data centers,” because that is our only hope.

Eric Ressler [00:33:40]: That’s our out.

Kaz McGrath [00:33:40]: Yeah, that’s our out. And incredibly smart people who are wise, who have been deeply involved in the climate space, in the environmental space, are saying that. And then the opposite end of the spectrum, of course, exists. But I think we need to have hopefulness for what we can reimagine together. I would’ve paid a lot of money to believe that Mamdani was going to be able to get in New York. I would’ve paid a lot of money to believe that all these things happened that surprised us. And that is when we reimagine what this needs to look like. I think we do need to demand of governments to support our systems. Will that happen? Maybe not. But maybe Bernie Sanders will live to 200 and be able to support us all through this. There is hopefulness in these. But I think the first step is believing that we can make that happen. And I truly, truly think we can. We’ve seen that in a one-hour workshop, and we’ve seen it in multi-month processes with people — that they can create better solutions. They just need to be guided along that process.

Stephen Silveira [00:35:00]: And like you said, it’s grassroots. We can’t expect the tech companies or government to do it for us. It’s the same thing — the tech companies are like, let’s do the advanced analytics without figuring out, all right, how does this all work infrastructurally and as a society?

Kaz McGrath [00:35:15]: But also, one thing I hope we do is we stop separating. We need government. We need these companies. We need the skeptics and the believers and everything. We need to have conversations with our elders who have lived through changes like this. In so many of these conversations, I’ve seen that one of the reasons why people are so scared or so unsure or so concerned is they haven’t been part of the conversation. We’re seeing this in Australia at the moment with discussions on IP infringement and musicians and authors — beautiful friends of mine having very powerful conversations. And that is because these decisions are being made for us, not with us. For us, not without us. And it’s in that space, I think, we need to, as a sector, step up into the role we can play. Because I’m not seeing people in these rooms, and the space is there for them to step up into it and to take it and be part of these conversations. And it’s not a conversation about productivity and using gen AI. It’s a deeper place.

Eric Ressler [00:36:25]: Before we wrap up, there’s one big topic I want to hit on that I think is really important. We touched on it very briefly at the beginning, but it’s worth its own segment — and it’s an intentional pun. You guys believe strongly in the power of play — play as a serious intervention. Let’s talk a little bit about that, because I don’t feel like our sector, and the current experience of being in a knowledge field, usually feels playful. It feels very serious. It feels sometimes corporate. It feels high-stakes. It feels urgent. And all of those things can be and are true. But I’m really intrigued to learn more how you guys think about how play can come in and be an intervention for positivity, both in terms of the experience and the outcomes of the work that we’re doing.

Stephen Silveira [00:37:10]: Yeah, it’s integral. Look at the threads we’ve just pulled on — it’s like, oh, it’s heavy. And I think that’s part of what we can bring: we can be that outside, more neutral party that can bring a group together and create a sense of play. And people’s shoulders can drop and they can have real conversations. And by the end of it, they’re like, wow, look how far we came. Wow, I never knew Joe thought that about this. There’s a million examples, but our ability to create that container of play is actually also creating safety, and it’s creating a space for creativity and just openness — so people can talk about these in a weird, complex, interconnecting way without worrying so much about having a solution every time. So that’s quite broad and hand-wavy, but I think our ability to create that container is really special, because to your point, people don’t get that enough. Maybe in the golden age of tech that was everywhere in the corporate space, but that was even only a sliver of people in the professional space. And it works. There’s data there. I think there’s a lot of data to back up that creating that sense of play leads to better outcomes.

Kaz McGrath [00:38:20]: Oh, there’s so much data. My team say to me in Zoom chats privately, “Don’t talk too much about the neuroscience,” because I’ll get on something and I’ll be explaining, I’m so ready — and they’re like, and the workshop’s over. We did a whole other podcast on me nerding out about it, but it’s science. It’s what our brains need. It’s what our brains need to be in a different placement of what area of our brain are we using. It’s what our brains need to retain differently. We’re not going to go to a five-year-old kid and present a PowerPoint on learning how to share. We’re going to play, and we’re going to share, and we’re going to go through the mistakes of that. And sometimes adults just need to admit that we’re all still kids and we have so many cognitive biases. And we like to pretend that we’re not filled with cognitive bias and flaws. I love reminding people about how much they love play, and then being able to show them that not only do we love play, but we just cracked through that really tricky topic. So for example, how hard is it to ask an organization, “Hey, what’s broken right now?” It can either be really uncomfortable, or people feel scared, or it can be filled with a whole heap of “everything’s wrong, everything has to change,” and it’s not a great feeling. But when you do that in a structured process with play that allows people to engage in different ways, we can tackle really difficult things. And also just creative juices — being able to get people into that imaginative space is really hard when you’re working in a nonprofit and you’re writing a grant proposal at 1:00 AM and you’re wearing five hats and you feel overwhelmed. So being able to pull people and support their brains in that space is really important.

Stephen Silveira [00:40:15]: And that’s more important than learning the tool, in our opinion. Someone leaving one of our workshops and feeling like imagination and playfulness and a willingness to engage it with curiosity is more important than them knowing exactly how to prompt perfectly for a specific use case. In our opinion — because we want them to go build what’s important for them. We’re not going to tell them just go do this thing and be dependent on it.

Kaz McGrath [00:40:35]: And for people listening — Conor Grennan, AI Mindset, has nailed this aspect of shift in mindset, and it’s a core part of what we do, which is: of course this is hard. This tool is brand new. It doesn’t work well with how our brains work. It changed an hour ago. It doesn’t work well with different forms of pattern recognition. There’s a reason why people who, like me, are neuro-spicy or neurodivergent can approach AI in different ways, because of the newness and the pivoting and, oh, well what about this, what about this — I’m just going to press the buttons more and more and more, and the exploration. And others struggle more with it. But it’s because we are retraining our brains to engage in a completely new technology. And we also have no idea what it holds in the future. So mix those things — mix political disruption and economic crisis and personal things and breakups and frantic work-life balance and all these things, and AI. Of course this is hard right now. So we do need totally different approaches to make this work for our organizations and our people.

Eric Ressler [00:41:50]: Love the topic around imaginative play. You mentioned watching kids — and we all have young kids in our lives in various ways, as we’ve talked about off the pod. When I watch my daughters do imaginative play, it’s so incredible, because you can see how it’s hardwired into their development in terms of how they learn, how they process. These games can get quite complex if you sit and actually pay attention and watch — you can see them problem-solve and develop as humans. And so it’s innate into our biology and our psychology. And then there’s this corporate world in which play is frowned upon — or not even play, but even unseriousness. But that’s the state in which the biggest problems actually get processed and solved, not the like, okay, we’re going to be in this rigid structure. And there’s a place for that too in the professional world and in the social impact space — we want it to be rigorous, we want it to be evidence-based. But I think we’ve leaned so far into that style of academic thinking that we’ve lost the humanness of it. And that might be my own point of view, and how we do the work and the type of work we’re exposed to. We’re not out there on the front lines all the time, and there’s a lot of folks in the space who are doing that work and see that humanity in their daily lived experience too. But that’s just my sense of the overall flavor of the sector right now. And I think it’s worth challenging and rethinking. And if there ever were a time to do that, it’s literally right now. It’s from the fallout of COVID. It’s from the fallout of all the DOGE bullshit and the USAID stuff being spun down, and the fact that the sector is so fundamentally unsustainable in terms of how and how much money is flowing and who makes those decisions and how that trickles down. To me, I see this opportunity, and I’m seeing discussions around — we can reimagine the sector, but we all have to do it. And I’m sensitive to like, oh, one more thing now that you have to do as a fundraiser writing a grant proposal at 1:00 AM. But it really does, I think, take all of us just deciding, and doing conversations like this, to imagine it together. So I appreciate you guys coming in. I’ve been really compelled by a lot of what we’ve been working on on the side, and just meeting you two — so I wanted to have you on the pod. I want to give you guys a chance to do a plug for our listeners who are like, okay, I’m sold. Where do I start? What can Play help me with? What other resources are there? Where would you guys want to point people?

Kaz McGrath [00:44:35]: Straight to our website — so weareplai.com, spelled wrong, so P-L-A-I. Reach out. If you are thinking bold and big and you want to really reimagine what things look like, reach out to us. Let’s have a conversation. For everyone out there working in the sector, we’ve just launched The Playground, which is always-on live experiences around AI and the skills and mindsets we need to be able to navigate all this wild change right now. We would love for people to join and be a part of that kind of growing community. And otherwise, say hi on LinkedIn, jam with us, share your favorite facilitation questions. Tell us if you are terrified or excited or have cool new things that you’re exploring.

Stephen Silveira [00:45:30]: That’s right. And we don’t play all the time, but we play a lot. So come check it out. And we believe pretty strongly that it’s not just for the C-level executive suite that should have these experiences of play and a well-facilitated space. So we’re all about how can we bring in lots of people from the sector, do those in big groups and still feel connected, but you’re not having to pay for a fancy offsite in the mountains. So yeah, come play.

Eric Ressler [00:45:50]: And so for our listeners, whether you are at the C-level and want to do a leadership-type thing, or bring your whole team or a particular department in — you guys have, I’m impressed by the kind of suite of offerings you’ve been designing. Everything from you can just do this on your own, if you’re within a nonprofit or starting a new social enterprise — you guys really do have a good suite of resources to meet people where they are, which I really appreciate. So to our listeners, go check it out. Kaz and Stephen, thank you so much for joining me today. This was fun. Thanks so much.

Stephen Silveira [00:46:20]: Cheers, man. Thanks for having us.

Eric Ressler [00:46:30]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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I have this problem, and I have it bad.

At Cosmic I’m the bottleneck on more things than I should be. Work piles up behind me, approvals wait on me, momentum stalls because it has to pass through my hands first.

Some of that is right. I’m the founder, I lead strategy, clients hire us to work with me directly.

The problem is the rest, the work I hold onto because explaining it feels slower than just doing it. It’s due, I’m late, so I tell myself it’s just this one time. Then I look up and I’ve done that one time five times.

Jonathan doesn’t get stuck here as often, and he pushed me on why.

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For him it comes down to self-awareness: knowing exactly what only he can do, being honest about what his team does better than he does, and being good enough at failure to let someone stumble a few times on the way to owning something. I’m still working on all three.

The talent on your team usually isn’t the problem. We went back and forth on where the line actually sits, what should stop with the leader and what we cling to out of ego or perfectionism.

I don’t think there’s one clean answer. The questions I keep coming back to are simple: am I the only one who can do this, am I the best one who should, and is being the person it all runs through serving the mission or just protecting how I see myself.

Episode Highlights:

[00:01:05] The bottleneck problem, named out loud
[00:03:05] Why being the bottleneck feels so bad
[00:05:05] The real fear behind not letting go
[00:07:15] Perfectionism and the near enemy of high standards
[00:09:20] The capacity gap you build without meaning to
[00:12:08] Right sizing your role as the stakes rise
[00:16:10] The ego question every leader has to confront
[00:17:12] Getting good at failure as a leadership skill
[00:21:00] “Just this one time” and how it multiplies
[00:25:35] What EDs and CEOs should actually own
[00:30:20] The time audit that pulls it out of your head

Notable Quotes:

[00:02:35]: “I’m a big believer in hire people that are better and smarter than you, and then let them cook.” Jonathan Hicken

[00:03:50]: “We have high standards at Cosmic. The near enemy of that is everything must go through me personally to hit those standards.” Eric Ressler

[00:17:35]: “I think one of my superpowers is I’m good at failure. I’m good at knowing what failure is acceptable and what failure is not.” Jonathan Hicken

[00:21:00]: “Just this one time I’m going to do it. And then all of a sudden I’ve done that just this one time five times now.” Eric Ressler

[00:26:05]: “You hear stories of executive directors copy editing every single email that goes out. That is the most catastrophic failure of that organization.” Jonathan Hicken

[00:29:20]: “It almost comes down to self-awareness. Being really aware of what your strengths actually are.” Eric Ressler

Resources & Links:

• Cosmic: Eric’s creative agency for nonprofits and mission-driven organizations

• Seymour Marine Discovery Center

• Science Solutions Santa Cruz podcast

• Drafting Our Strategic Dream Team: Eric and Jonathan’s past episode on YouTube

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:01:05]: All right, Jonathan, I’ve got a juicy one today. So the topic today is, how do we get EDs, executive directors, CEOs at social impact orgs, out of the bottleneck position?

Jonathan Hicken [00:01:25]: In the sense that we’re blocking stuff from getting done?

Eric Ressler [00:01:25]: Yes.

Jonathan Hicken [00:01:25]: Yeah. Okay. Man, there are so many reasons and so many opportunities. Let’s go.

Eric Ressler [00:01:35]: So this is something I see sometimes, not all the time. And let me just have a moment of vulnerability here. I have this problem and I have it bad. And some of that I think is actually not always wrong. There are certain things that at Cosmic I should be the bottleneck for. I should be the owner for. Probably the same for you. But also, I’m impressed with how you run the Seymour Center, how you empower and build up the team and not be the bottleneck on things that you shouldn’t be the bottleneck on.

Jonathan Hicken [00:02:05]: Oh, thank you. Thank you.

Eric Ressler [00:02:10]: So tell me, spill all the secrets. How’d you do it?

Jonathan Hicken [00:02:10]: Oh, man. Okay. The thing that comes to mind first is a deep understanding of what I am personally good at, especially as it relates to the rest of my team. What am I uniquely capable of doing, both in my skillset and in the time that’s available? And the same goes for everybody on my team. What are they uniquely good at? I’m a big believer in hire people that are better and smarter than you, and then let them cook. So it’s being uniquely aware of what they’re good at, and trusting them to go. Setting guardrails on when I need to know about things and when I don’t, and making sure that’s really clear. I could keep going, but let me pause. What’s going through your head immediately?

Eric Ressler [00:03:00]: I’m speaking partly from my own experience at Cosmic and also observing a lot of executive directors who are the bottleneck. Let me just start by saying, when you are in a bottleneck state that is beyond what’s right, and you can sense that, it sucks. It feels bad. I can feel it when I’m in that position. And I can feel it when I work for people or with people who I can tell are in that position too. It leads to all these downstream problems where things pile up, they don’t get solved, momentum gets lost. Everything has to go through the executive director before it gets approved. And there’s parts of this that I struggle with. Part of it is because we have high fucking standards at Cosmic, and I’m proud of that. But the near enemy of that is everything must go through me personally to hit our standards. This is a nuanced thing, because we’re a small team. When you work with us, part of it is you work with me directly. I’m the founder. I lead a lot of our strategy work. So some of that’s not even wrong. But where I feel sensitive to it is where it’s like, I know I shouldn’t be doing this thing, but it’s easier for me to just do it than to work through it with someone on my team, because it’s due and I’m late on it. These are the excuses that go through my brain that even as I’m doing them, I’m like, this isn’t right, but I’ve just got to white knuckle it and get it done. And I think that happens a lot for people. So is it my perfectionism? Is it my lack of organization? Is it some of those things that hold me personally back here? Or is it deeper than that?

Jonathan Hicken [00:05:00]: Well, let me ask you a question. When you’re feeling that bottleneck thing, what is your fear? If you were to let somebody else on your team take it, what’s the fear there?

Eric Ressler [00:05:15]: First, there’s the caliber fear. When we’re doing work for clients, we want to come through on our promise that we’re going to deliver S-tier caliber work. And my team is capable of that, especially for the things they’re uniquely qualified for. There are things everyone on my team is way better at, at least ten things, than I am. And then there’s the stuff that doesn’t fit neatly into that box. You hire a team because you get more than one person. Even though we have specialty, the true value is in the collaborative nature of our entire team. Co-creation is a buzzword, but truly, oftentimes we’re unlocking the ideas through collaboration with our clients.

Jonathan Hicken [00:06:10]: Yeah. Your team is incredible and they’re amazing at what they do, but clearly there’s still a disconnect. Because if that were plainly true, you wouldn’t have this problem. Which makes me think, are there certain skills that either you’re not hiring for or that you’re not developing within your team that’s creating this gap, where you’re the only one who holds that particular talent or scope?

Eric Ressler [00:06:40]: There are parts of the team structure where things do fall squarely on my plate to do the work for clients.

Jonathan Hicken [00:06:50]: As they should.

Eric Ressler [00:06:50]: For clients is one flavor of that. Also, big picture strategy work for Cosmic, that’s my job. I don’t want to delegate that. I want to include the team, but that’s not something I’d ever ship off to one of our designers to figure out.

Jonathan Hicken [00:07:10]: Business operations, whatever. You want them thinking about client work.

Eric Ressler [00:07:15]: So back to the core questions, why does this happen for me? One is, we’re delivering important client work and I want to come through on my promise to clients that I’m going to be part of that work. It’s not always easy to fully delegate. There’s stuff that absolutely I can and do delegate all the time, but there’s also stuff where I feel like I can add value and have an impetus to do that. So, full disclosure, some of this is my own perfectionism, my own care and passion and deep integrity. I want to make sure a client never feels like we aren’t coming through on the promises we made to them.

Jonathan Hicken [00:07:50]: Well, what I’m hearing from you is that you see yourself as the holder of a certain type of integrity that nobody else is capable of meeting.

Eric Ressler [00:08:05]: I think that’s the dangerous place to get to, because I actually don’t think that’s true for our team. And I say that with pride, in the sense that I’m proud of the team that I’ve built.

Jonathan Hicken [00:08:15]: I trust that too. I’ve worked with them. They’re amazing.

Eric Ressler [00:08:15]: It’s true to a degree that in my mind, as the founder of the agency, ultimately the buck stops with me, in the sense that any problem is my responsibility. Not necessarily to solve, but I own it. I’m never going to throw a teammate under the bus, because even if they did something quote unquote wrong or not to our standards, that’s still my problem as the founder of the firm. So there’s some element of that. But if you take it too far, it can go to a place of lack of trust, or perceived lack of trust, and that can be felt by the team, or by the client, or in the case of a social impact org, the supporter or the beneficiary or the partner. So I’ve been doing a lot of work on that. Some of it is training. Some of it honestly is systems. Some of it is permission. Some of it is my own letting go, my own self work of how much of this is imposter syndrome or whatever else.

Jonathan Hicken [00:09:20]: Let me put a positive spin on this. What you’ve done really well is define the roles and responsibilities of the people on your team so clearly that it enables them to be successful and creative. You’ve set them up for success in their particular role, and that’s laudable. That’s something leaders should do. But what you’ve unintentionally created for yourself is this gap of capacity to do the kinds of things you’re uniquely capable of doing. That doesn’t necessarily need to be true. Now we’re talking about bringing other people onto the team, and there’s, can we afford that, and a lot of other questions.

Eric Ressler [00:10:00]: This is exactly where it gets nuanced. I’ve made some strategic choices about who we are and what that means for my role as the founder. This is often also true for nonprofit executive directors or social impact CEOs. A lot of it is team size. We’re right now an eight person agency. By definition, all of us are going to wear more than one hat. We’re not big enough for each of us to have one singular role that’s 100% of our time. As you get bigger, you have more team support and maybe you start to delegate, shed, or reassign some of those roles to specialists. Think about even the two person new-idea nonprofit, you’re both doing everything all the time. That’s natural. So some of this is around strategic choices I’ve made to stay small. And another strategic choice is I want to stay deeply embedded in the work right now. I like doing the work. It keeps me motivated, keeps me grounded, keeps me real about how we position ourselves. Not as an academic or theoretical exercise, but grounded in the actual pain and problems our clients serve, because I’m in there in the trenches with them.

Jonathan Hicken [00:11:30]: You realize you’ve created a pretty risky problem for yourself as Cosmic grows. And by grow, I don’t necessarily mean team size. In terms of impact, as you take on more and higher stakes work, the stress on you is going to continue to grow. That’s not going to get smaller in the structure you’ve built. And by the way, we’re using you as a case study here.

Eric Ressler [00:12:05]: A case study, unintentionally.

Jonathan Hicken [00:12:05]: But the same goes for any executive director in the same position. You aspire for deeper impact, for more important work, and you as the executive director need to hold some of that. I do, in my own role. And what I’ve learned is, as those responsibilities scale for myself, you have to right size everything else going on in the organization. I can’t keep doing the thing I was doing last year, because I need to make space for this. So now I have a tough decision. Do I kill the thing I was doing and we’re just not going to do it anymore? Sometimes that is the case. Or do I delegate that to somebody else on the team, which puts them in a position where we need to kill something they’re doing. Ultimately, I think that’s how teams up-level over time, this cascade effect of taking on new things and killing other things. And sometimes we as executive directors get in the position where we don’t do the killing part. The result is we become that bottleneck, because it just builds up to the top and we have to hold onto it.

Eric Ressler [00:13:15]: Yeah. I’ve definitely experienced this, and I’ve seen other executive directors experience it too. Some of this, for me, is intentional choices I made. We were talking about this before we were recording. In our current trajectory, we’re positioned intentionally as a practitioner-led, bespoke design and brand strategy firm, which means people expect to work with the founder at a small agency. A downside of working with a big agency is you meet the founder, you get the pitch team, and then the work starts and you get handed off to the B team. That’s something I’m sensitive to. I never want that to be the experience. So I’ve made some choices that lead to me being involved in client work, which means I can’t also do X, Y, Z. And how we define growth is not only headcount. The way I think about growth is we do deeper, more impactful work for more impactful organizations. It does mean there’s more pressure on me, higher stakes on me, but for the whole team, so it gets distributed. But I still am the bottleneck in ways that are good and right, but also at times in ways that are bad and wrong. That’s a really important distinction. The easy way to think about it is, am I the only person who can do this? Maybe, maybe not. Is that right or wrong? Maybe it’s right, maybe it’s wrong. Am I the best person to do this? Maybe, maybe not. A very simple set of questions you can ask. What are the parts that energize me and light me up? And what are the parts that feel like a total brain drain? There are parts of the work I could do all day and you wouldn’t have to pay me. And there are parts that are just the necessary grind of being a business. Those are the things I reach for first to try and either hire up for or delegate. So that’s one way I’ve personally worked through this.

Eric Ressler [00:15:20]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:16:10]: We have to confront ego in this conversation. And that’s not just for you, not just for me, but it’s part of the reality of carrying this title or this role in our organization. Is this something I’m doing because it validates my sense of who I am and what I can bring to the table? Or is this about what I think is best for the organization? And those two things don’t always align.

Eric Ressler [00:16:35]: They don’t always. They do sometimes though.

Jonathan Hicken [00:16:40]: They do sometimes though. And when you find that, that’s kind of the sweet spot. This is best for the organization and I love doing it and I’m good at it.

Eric Ressler [00:16:50]: That can be a sweet spot, but it also has, in my opinion, a limit. Because that can all be true and you could still be a bottleneck and way over capacity.

Jonathan Hicken [00:17:00]: Well, that’s true. You may have hired the wrong team and so you create this condition where you really are the only person who can do that thing. But the fundamental thought here is there is ego in this.

Eric Ressler [00:17:10]: 100%.

Jonathan Hicken [00:17:15]: I had a coworker here. We went on a walk for one of our check-ins and he said, “Jonathan, something that’s really unique about you is that you don’t take anything personally. And the rest of us do.” And he said, “You actually need to be careful about that.” One of the things I took away is that I think one of my superpowers is I’m good at failure, and I’m good at knowing what failure is acceptable and what failure is not. Especially in this role of delegating or trusting the team, I have a keen sense of, it’s actually okay if we fail on that, or it’s okay if we fail a couple times as part of that person’s learning process. I go into these conversations knowing, and often communicating very clearly, this probably is not going to go very well the first few times you do it. Eventually this is where we need to be, this is what success looks like, but it’s going to take some time to get there, and it’s okay if you fail. Now, the work we do is relatively low stakes in the big scheme of the world.

Eric Ressler [00:18:25]: At the Seymour Center?

Jonathan Hicken [00:18:25]: Yeah, yeah.

Eric Ressler [00:18:25]: To a degree, yeah. Compared to some other orgs.

Jonathan Hicken [00:18:30]: Compared to some other orgs, right. So there’s a certain degree of failure we can play with, and I want to acknowledge that. But my ability to not take things personally and accept failure in some situations, and maybe this gets me in trouble sometimes, is part of what allows me to create the space for the team to take on these new responsibilities.

Eric Ressler [00:18:55]: Yeah, I think that’s dead on, because I’ve definitely had times, and I’ve observed this in other executive directors too, where it’s like, well, it has to be me because I’m the only one I know isn’t going to screw this up. Sometimes that might be real. But if that’s always the case, and there’s a pattern there, it points to some potential problems. In the past, I’ve had that experience where I’m like, well, if that’s true, that’s actually a big problem for a model. That’s not scalable, that’s not sustainable. So why do people get stuck in these roles, this scenario where they become the bottleneck in perpetuity? This is something we frankly deal with sometimes, where we can’t get approvals on things because we can feel that executive directors are the bottleneck on other parts of the org, so they don’t have the time we need them to give us in order to do our work. So we see it from that purview. Why does this happen? Okay, failure’s not an option and they’re the only person who can do it. Or the cost of sitting still to create the new system or do the training always feels like it’s not worth it. This is something I run into sometimes, where it’s like, well, I could delegate this, but it’s actually faster for me to just do it, because I know what I want and I know I can do it. It’s faster than trying to explain it to someone, develop my thoughts, give it to them, have them do it, then review it. So you could come back at me and say, well, dude, you’re not actually delegating. You’re just overseeing. That’s a difference. True delegation means you hand it off and you trust it’s going to be taken care of.

Jonathan Hicken [00:20:40]: Well, that’s a little oversimplification. You need to set people up for success, define what success looks like, all that stuff. But fundamentally, dude, you know it’s an investment, right? And investments take time. That is the cost of doing business in some cases.

Eric Ressler [00:21:00]: And here’s the trap. Just this time, just this one time I’m going to do it. Just one time. And then all of a sudden it’s like, well, I’ve done that just this one time five times now. And if I had just done it the first time, I wouldn’t have had to do it the other four times.

Jonathan Hicken [00:21:10]: I want to talk about accountability in this too. One of the things that works in my team is that we’re very results oriented. Everybody on the team, regardless of role, has a clear sense of duties and a clear sense of measurable results they’re accountable to. Because we’re also a small team, ten full-time staff, there’s a lot of collaborating and sharing and wearing multiple hats, but everybody’s an owner of something specific. I’m often involved in the work in some way. But the reason delegation can work, and the reason I don’t get caught in the bottleneck trap as often, is because if I’m holding somebody accountable to a measurable result, and I am the reason they’re not hitting their result, they know they’re allowed to call me out on that. They’re allowed to hold me accountable to my role in helping them be successful. That clear set of expectations, clear roles, and a culture receptive to giving each other tough feedback in every direction, that unlocks my ability to make those decisions about where I should or shouldn’t be involved.

Eric Ressler [00:22:30]: So I’d love to hear from your perspective, clearly you’ve thought deeply about this. How do you make a choice about what is squarely your role and responsibility, the things that only you could or should do, versus the things you shed? For example, recently you’ve taken an intentional step into being much more of the PR arm of the Seymour Center, through the Science Solutions Santa Cruz podcast and other things. That’s a lot of time and energy. That time was being spent somewhere else. So have you had to shed some things? How do you think about balancing all of it?

Jonathan Hicken [00:23:15]: I was actually going to use the Science Solutions Santa Cruz podcast as an example. Every step of the way in this organization’s development since I’ve been here, I’m constantly asking myself, what does the organization need in order to reach the next step? What’s missing today that needs to exist a year from now? And how is that going to happen? Oftentimes my role here has been the initiator, starting the new thing, with a clear sense in my head of, if I start that new thing, what happens a year from now when I’m no longer doing it? I think about that with the podcast too. I knew coming into this year that my most important contribution to the Seymour Center’s success was going to be money and visibility. Funding and visibility. Those were the two things I needed to focus my personal attention on. The podcast was one of the ways we’re going to work on the visibility part. And I asked those same questions. Who is most uniquely capable of doing that particular role? At that time, that was me. I am the person most positioned to do that piece. But even coming into this venture, in my mind I’m already thinking about who’s going to be the next host, what’s the next show going to be, how are we going to grow this, so I don’t actually have to be that, but the quality and impact of that venture doesn’t decrease.

Eric Ressler [00:24:45]: Which doesn’t necessarily mean you’ll make that choice, but you’ve at least thought about, am I signing up for something in perpetuity here? And to a degree, you kind of don’t know until you try, but you’ve got a contingency plan in place.

Jonathan Hicken [00:25:00]: Right. And look, I hope we don’t kill the podcast anytime soon. And if we do, that’s not the end of the world. We’re going to be fine. I continue to believe in it and I continue to spearhead it. But I’m already thinking about, what is required of the host or the producer to make it successful? And is there a world in which somebody else could do that? I actually think the answer’s yes.

Eric Ressler [00:25:25]: I think so too. So at a high level, maybe we could riff on, what should EDs and CEOs actually be responsible for, at large?

Jonathan Hicken [00:25:35]: I’m not sure there’s one answer to that. And I authentically say that, because every organization has a different composition of people and talent, problems, ecosystems. But what is required is that the executive director is keenly aware of their own skillset as it relates to everybody else’s around them. It’s your job to find that Venn diagram, that little slice where you’re like, I am going to accelerate our success or our impact if I take this role. You hear these stories of executive directors who are copy editing every single email that goes out, and I’m like, that is the most catastrophic failure of that organization, because there are a million people who can write a good email. Most people on your team can write a fine email. I’m not uniquely capable or positioned to do that work. But maybe some of us fall back to it because it’s safe, because it’s easy, because whatever. So to answer your question shortly, I really don’t believe there’s one thing.

Eric Ressler [00:26:45]: I think that’s fair. If there were one thing, and this also is maybe not this cut and dry, I think that for most orgs, the CEO or executive director should own vision for the org. And I don’t mean that vision should be only theirs, or that it shouldn’t be informed by others. We just did our fantasy drafting episode of your strategic team, which was super fun, and we talked about all the people who should be part of your strategy and your vision. But I do think at the end of the day, for most orgs, vision should squarely fall in the ownership of the CEO or the executive director. Maybe even deeply informed by many other stakeholders, but at the end of the day, who’s going to sign off on it and spearhead it or initiate it? Agree?

Jonathan Hicken [00:27:35]: No.

Eric Ressler [00:27:35]: Okay.

Jonathan Hicken [00:27:35]: I think in reality that’s probably 90% true for most organizations. I think that’s widely true.

Eric Ressler [00:27:40]: But not 100%.

Jonathan Hicken [00:27:40]: But not 100%, right. Because you might have someone on your team who is an incredible storyteller and they can tell a fucking story. And you’re the executive director, you’ve got that title. Some executive directors would be like, okay, I’m going to be the one who stands up and tells the story, even though I’ve got this powerhouse on my team. But that’s where that awareness comes in. Where you’re like, actually, I’m more of a finance ED, or I’m more of a programs ED, but that person’s a hell of a storyteller. I want them really owning the articulation of where we’re headed.

Eric Ressler [00:28:15]: Yeah. That’s slightly different than what I was thinking of, but I hear what you’re saying. It actually maybe works for vision too. So I’m going to say I agree generally that there’s no every ED or every CEO must own these parts. So maybe the better way of thinking about it is, what are my unique strengths, even as an executive director or CEO? You talk about the finance CEO. That’s legit. I’ve worked with some CEOs and executive directors who are really weak on some of those other things that other CEOs are good at, but man, can they run the books. And because they’re so good at that, and because they have the rest of the team to support their deficits, that is the best thing they could possibly do. Then their org is greatly resourced. They’re not constrained. They don’t have the scarcity mindset.

Jonathan Hicken [00:29:05]: Exactly.

Eric Ressler [00:29:05]: I don’t think there is even, and it’s so obvious in hindsight, there’s not any one flavor of a CEO or executive director. So the clear takeaway for me so far is, it almost comes down to self-awareness. We’ve been talking about that a lot on the show, because it is so important. Being really aware of what your strengths actually are. And the ego thing, which we touched on, I think is so true. And frankly, something I struggle with. Even as someone I think is pretty humble overall, there are things where I’m like, no, this should be me. And how much of that is ego versus truth? I don’t think those things are perfectly aligned.

Jonathan Hicken [00:29:45]: I was just coaching someone on my team who recently got a promotion, who’s stepping into a leadership level she hadn’t been in before. I believe she has the skills to do it. One of the things we talked about is, hey, you’ve got a team of people who are really, really capable at X, Y, Z thing, and right now you’re still too involved in it. You actually need to step back. You need to define what success looks like, but the essence of the coaching was, what are you uniquely good at? What is your team uniquely good at? And it’s time to make space for both of those.

Eric Ressler [00:30:25]: I think that’s true. And in reflection, as we work toward wrapping this up, even in those moments where there may be some ego involved, maybe there is, maybe there isn’t, it just feels like crap to be the bottleneck. No one wants to be that. What I think about a lot is when I’ve found myself in that state, and it happens, it ebbs and flows. Luckily at this point it’s still a problem, but I’ve done a lot of work with the team to figure out how to release it. And it’s a constant thing, because it’s not static. We’re constantly moving and changing, adding new initiatives. Oftentimes, similar to you, I’m spearheading some of those. I’m trailblazing it, testing it, experimenting. And then at some point I need to delegate, hand off, operationalize it. So it’s this always fluid thing. But what I’ve found most helpful is, when I find myself in that state, I literally sit there throughout the week over the course of a couple weeks and write down everything that I do. And I score things. Love this, hate this, drains me, however you want to score it. Then you just look objectively back at how you’re spending your time, and is that the right way I should be spending it? That’s a good exercise, because it takes it out of the abstract, out of the conceptual, out of the emotional. It’s just, objectively, what did I do, and is that what I should be spending my time doing in my current role, in our current trajectory as a company?

Jonathan Hicken [00:31:55]: Yeah. And you could do that, obviously if you have a giant team this is less possible, but you could do that for the other people on your team. You should. Here’s what they’re doing, here’s what they’re succeeding at, here’s what they’re not. That’s the exercise when you do it for yourself and your team. Now you’re starting to see, oh, okay, here’s really the mosaic of the skills on this team, and that might unlock some insights about how you might move work differently.

Eric Ressler [00:32:20]: Yeah, I think that’s right. So hopefully some of these tips and this way of thinking about it leads to some of these bottlenecks going away, or at least getting a little bit wider, for some of our listeners. Thanks for sharing all your secret sauce, Jonathan.

Jonathan Hicken [00:32:35]: Yeah, thank you, Eric.

Eric Ressler [00:32:35]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Every social impact leader wants more people to know about their work.

Almost none of them want to be the one posting about it. Putting yourself in front of an audience feels like ego, or a distraction from the mission, or simply not something an executive director has time for.

The reasons leaders give are genuine: not a comms person, not trying to make it about themselves, afraid of getting it wrong. None of that explains why the work still isn’t reaching who it needs to reach.

In this episode, Saralynn Finn and I dig into what changes once someone gets past that resistance: story stems, a repeatable format for turning an ordinary moment into a post worth reading, and the difference between posting out of obligation and posting because something actually needs saying.

The approach holds up because it’s built on evidence: which patterns actually perform, why a personal page beats a brand page every time, and how long it really takes for a post to reach its full audience on LinkedIn’s slower-moving algorithm.

Saralynn brings real client stories into it, including a nonprofit CEO’s 90-day experiment that changed her mind entirely. I bring my own inconsistent LinkedIn habits too, admitting exactly where I’ve fallen off since the two of us last talked.

This is a second conversation, picking up where an earlier episode on visibility left off. By the end, it’s got me wanting to get back in the game.

Subscribe now

Episode Highlights:

[00:02:00] Why LinkedIn is the fastest-growing platform for anyone over 30
[00:04:00] Story stems: the copy-meme format built for LinkedIn posts
[00:06:30] Story stems get three times the engagement of posts without them
[00:10:00] Madeleine Ballard’s 90-day LinkedIn pilot, and what it actually delivered
[00:14:00] “Get over yourself”: why nobody’s presence is too small to matter
[00:16:00] Eric’s own LinkedIn burnout, and what caused it
[00:18:30] The three kinds of posts: keeping the lights on, building the muscle, and the ones you can’t not write
[00:20:30] How often should you actually post? (Not as often as you think)
[00:23:00] Personal pages vs. brand pages: where ideas actually travel
[00:26:00] The sector’s discomfort with admitting failure in public
[00:29:00] Authenticity, sanitized brand voice, and what political campaigns already figured out
[00:34:00] Why LinkedIn rewards patience: posts take three weeks to peak

Notable Quotes:

[00:06:25]: “Story stems, posts with familiar patterns, get three times the engagement of posts that don’t have a story stem.” Saralynn Finn

[00:16:05]: “I’m feeling a little burnt out by LinkedIn right now, and it’s my own fault.” Eric Ressler

[00:21:10]: “Anything you’ve done is better than doing nothing.” Saralynn Finn

[00:23:05]: “Personal pages have the highest likelihood of having your ideas travel far.” Saralynn Finn

[00:28:55]: “Authenticity, it matters. People can feel it instantly.” Saralynn Finn

[00:33:20]: “This humility does not require invisibility.” Saralynn Finn

Resources & Links:

• Community Health Impact Coalition — global coalition making professional community health workers standard practice.

• Dr. Madeleine Ballard — CEO of Community Health Impact Coalition and 2025 Skoll Award for Social Innovation recipient.

• The Sidebar — the Skoll World Forum fringe event in Oxford where Saralynn ran the workshop.

• Saralynn Finn — guest’s site and consulting practice.

• Visibility Beats Impact — Designing Tomorrow Podcast episode, April 2026

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:00:50]: Saralynn Finn, welcome back to Designing Tomorrow and to Seymour Studios where we record. There was more to talk about, so I thought, let’s do another episode.

Saralynn Finn [00:00:55]: So much to talk about, Eric. I’ve really enjoyed getting to know you over the last few years, and especially these last couple of months as we prepared to go to the Forum together. I really appreciated your support with the workshop I ran at The Sidebar, and having you chime in with your experience on LinkedIn and growing your personal brand was amazing. I’m excited to share it with your audience here on the podcast.

Eric Ressler [00:01:25]: We thank you first of all for inviting me to just crash your awesome session and get to meet some amazing people in Oxford. And I do think there’s more to unpack here. So I’d like to first interview you a little bit and ask how you came up with this point of view, this framework, this way of showing up specifically on LinkedIn, but I think it applies outside of LinkedIn too. Let’s talk about that. Why LinkedIn?

Saralynn Finn [00:01:55]: Absolutely. Why LinkedIn? It’s the fastest-growing platform for really anyone if you’re over the age of 30.

Eric Ressler [00:02:05]: Which is many of us.

Saralynn Finn [00:02:05]: Yes. Okay, so we can’t compete with the TikToks. I don’t want to be dancing, at least professionally. But when I show up professionally, that’s the place, and there’s so much opportunity. But as we were talking about, it’s not all about LinkedIn, right? It’s about relationship building, and it’s about being willing to be visible and vulnerable. I loved the episode you dropped recently about visibility, and the connection it makes to this work we were already planning on doing, which I think was just, dare I say, cosmic?

Eric Ressler [00:02:45]: It was a little cosmic, yeah. What I’d say is visibility is this topic that everyone’s thinking about. So I’m excited to talk about this, because we did the episode about visibility, I made a case for why it matters and how to think about it the way I think about it, at least. And then another episode about point of view. I think those two things, especially where I think LinkedIn comes in, is: LinkedIn, in my opinion, is the platform where if you have a really strong point of view, a differentiated one, you can get visibility. And that’s always at the whim of the algorithms, we could get into all of that. But I think listeners are probably like, “okay, I’m interested in being visible, I know I want to do that, I’m working on developing a point of view, but I’m scared.”

I’m scared to go on LinkedIn. I don’t want to be vulnerable. I don’t want to be public in my work. And I’m happy to share my experiences with that, I’m sure you’ve experienced that to a degree as well. But let’s start, before we get into all that, by talking about this concept you call story stems, which is a nice way to get started if you’re first getting into LinkedIn, but also even if you’ve been there for a while, right?

Saralynn Finn [00:03:55]: Absolutely. What I want to bring to your audience today is a few hacks to make the threshold between never posting and occasionally posting feel way more achievable, something you could do on a Thursday afternoon before you wrap up your workday. Story stems is one of my favorites. I like to think of them as memes for professionals. We’re all familiar with memes. Why memes work is because it’s a format we’re familiar with, and then the creator adapts that format in some novel, creative way that connects to the moment. Maybe it’s Forrest Gump sitting on that bench, and it’s something witty about something you’ve been waiting to happen. We get it, we connect with it, it’s understandable. Story stems are like that, but for our copy. A lot of times people lead with a question or a pattern. I think our proliferation of AI LinkedIn posts has really leaned into the pattern, but it’s still a good story stem. And the one that [00:05:30] I like the most is “recently I met,” insert someone you met recently. And what we know from that story stem, that copy meme, is you’re going to get a post that likely celebrates the person the poster just met. You’re going to get a human moment where they interacted, and you’re probably going to get a reason why the poster is sharing that with their audience: why this matters, what resonates, what’s the insight this person gave that connects. So to me, the story stem is a very evidence-based option. These different options I laid out, the insight, the pattern, “I met someone.” Story stems, posts with familiar patterns, get three times the engagement of posts that don’t have a story stem.

Eric Ressler [00:06:35]: Interesting. Okay, let me make sure I’m understanding this correctly. First of all, I should say one of my favorite life cycles of me posting on LinkedIn was when I was very meme-heavy in my posting, and I’m feeling like I want to bring that back. They actually performed better than some of my more serious posts. Not totally surprising. But what I’m picking up from these story stems is that they’re a hack because they build in this human moment.

Saralynn Finn [00:07:05]: I’m going to correct you.

Eric Ressler [00:07:05]: Oh, go ahead.

Saralynn Finn [00:07:05]: Yeah. They’re a hack because they build in something the audience can expect. The audience knows what they’re going to get. There’s a format that’s familiar. And we love novelty, novelty is what we’re looking for, but we want a small amount of novelty.

Eric Ressler [00:07:30]: Okay.

Saralynn Finn [00:07:30]: And that’s what the algorithm is oriented toward, unfortunately: giving us something in packaging that’s familiar, but with just a little something new.

Eric Ressler [00:07:40]: Yeah, I resonate with that. I think there are these cycles. I’ve spent a lot of time thinking about what breaks through and why. Even just as I’ve been publishing for a long time, on and off LinkedIn, I’m happy to share my current, maybe not ideal, state of LinkedIn posting. What I’d say is there seem to be these ebbs and flows of patterns. You talk about story stems working and being evidence-based because there are these patterns. And what I’ve noticed is there’s a certain point where I think some patterns are durable, they’re going to work always, and I think that third example I picked up on, the human side, is maybe one of them, maybe not. But then there are these moments where the patterns get oversaturated, and there’s a new, totally novel pattern or approach that starts to break through, that’s literally a pattern interruption. And that pattern interruption is like, oh, I noticed that. If I’m scrolling my LinkedIn feed and all the posts look like AI slop, and then there’s one that’s just some dude who’s like, “Hey everybody,” that becomes a pattern interruption. So I’d be curious to hear, you have these hacks, these story stems that are tried and true, evidence-based. If we’re talking to listeners who just want to get started, I love that easy on-ramp. At what point, and how do you know how long to ride that, and when it might be time to think about inventing a new pattern or a new story stem?

Saralynn Finn [00:09:15]: I think that when you’ve achieved your goals for visibility is when you start to mix it up. But in terms of training the algorithm on who you are, who you want to reach, and who you want to be seen by, stick with what we know works. While you’re getting comfortable with posting and figuring out the posting cadence that actually works for your real life, on top of all your other responsibilities, I don’t want to minimize the impact posting on LinkedIn has. In fact, I’d love to share a story from Madeleine Ballard, who’s, I think her title is Executive Director of Community Health Impact Coalition, a 2025 Skoll Award recipient among other amazing accolades, and work that’s made it so that millions, potentially billions, of people all around the world have access to community health workers.

Eric Ressler [00:10:20]: Amazing.

Saralynn Finn [00:10:20]: She’s incredible. And she was really anti-posting on LinkedIn. I think her point of view is going to sound really familiar to a lot of your viewers and listeners. She felt like, “who am I to be posting on LinkedIn? I’m a white woman leading this global organization. The people doing the work should be the ones who are out in front, they should be the ones who are visible.” So that’s a common one. “I don’t have time to do this. This is not mission-oriented, this isn’t going to move the mission forward for the organization. It’s vanity, it’s ego, it feels promotional.” And then there’s also, “what if I get it wrong?” Which, yes, sometimes we get it wrong.

Eric Ressler [00:11:15]: Everybody gets it wrong.

Saralynn Finn [00:11:20]: Sometimes they’re going to come for you in the comments, and that’s the risk we take in being visible, so I don’t want to discount that. Madeleine didn’t want to post on LinkedIn, and she had a comms person who said, “what if we just did a 90-day pilot and tried it out and saw what the results were?” She was so angry, at the end of the 90-day pilot, to see how successful it was in growing her organization and her personal impact. After 90 days, she said she had more inbound press inquiries than they’d ever had. Her warm introductions were getting responses. A publication she’d submitted articles to multiple times reached out and said, “would you be willing to write an article for us?”

Eric Ressler [00:12:15]: The one she’d submitted to before, yeah.

Saralynn Finn [00:12:20]: Exactly. And there were funding doors opening. Look, Madeleine is a powerhouse, Chic is an incredible coalition built on an amazing strategy. So I’m not going to say everyone who posts on LinkedIn for 90 days is going to experience these incredible results, but what if? What could just doing it for 90 days, what could that impact be for you and your organization? And it doesn’t have to be original. You’re probably not a comms person. You’re probably feeling like creativity isn’t something you have the energy for in this realm, especially if you haven’t seen it deliver impact for you yet. I’ll tell you, once Madeleine saw the impact that posting regularly and with some intention delivered, she was on board. I highly recommend you follow her on LinkedIn if you don’t already, her posts are really great. Do what she’s doing.

Eric Ressler [00:13:30]: Yeah. This is making me feel guilty that I’m not running a better LinkedIn motion right now for myself and for Cosmic. All the reasons you outlined are common objections I hear and resonate with. I love doing our show, I love having a podcast, I love sharing ideas and getting feedback from listeners. And I still cringe when I hear my voice or see myself on camera. I have some worry about being public in my work. At the same time, I’ve also felt at times that people who have that point of view, there are lots of reasons you might come to that conclusion, but sometimes it’s also like, and I said this in a recent episode, it’s a little bit of a contrarian take, but it’s kind of like, get over yourself. You’re not that special. You can post on LinkedIn too. You’re not so special that you’re too good for it, but that doesn’t mean you don’t deserve to.

Saralynn Finn [00:14:40]: I’ve thought about the privilege we currently have of having LinkedIn. Imagine people trying to move social impact ahead in the 1800s. They would’ve given their left arm to reach as many people with their message as we can potentially reach in just three months.

Eric Ressler [00:15:00]: Huge point. Huge point.

Saralynn Finn [00:15:05]: Get over yourself.

Eric Ressler [00:15:05]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back, we roll up our sleeves and help you bring ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Let me reflect back some thoughts in real time, because I’m going to come out with an honest statement. I’m feeling a little burnt out by LinkedIn right now, and it’s my own fault, because I truly do believe you can complain about the algorithm, visibility, reach, the incentives of these companies, the attention economy in general, all of that, and at some level I believe there are real problems that need to be solved there. And at the same time, it’s such a gift if you approach it with the right intentions. There was a moment in time where I had this real focus around being dedicated to posting more regularly, getting clear about what my modality is going to be for posting and my vibe, and to learn and get data and work on that. I think there were a lot of really good lessons learned there. But if I can reflect on where I went too far, and what I’m hoping to change when I do come back in a more meaningful way, I felt like at a certain point I was posting out of obligation instead of inspiration. I think that’s what a lot of people feel once they get past the initial hump and start to say, “I need to do three days a week.” This is something we hear, we heard it in our session. There’s a kernel of truth to cadence, for sure. But what I found is that when I post because I feel inspired to, those posts tend to do better. My most successful posts, by every metric, reach, engagement, resonance, inbound, all the things you might measure, the posts I just typed out on a whim because something irked me, or because I had an idea with my thumbs, always perform way better than the ones I had a nice piece of art pre-scheduled and posted for. So what are your reflections on all that?

Saralynn Finn [00:14:55]: Okay, both matter, right? We have to do the KOL, the keeping-the-lights-on posts, putting ourselves out there for the building-the-muscle aspect of doing the thing, getting comfortable, and learning. The only way we learn what works for our audience is by experimenting. If you’re not giving your comms team the room to learn and experiment, that’s maybe a little aside. And when you do have the zeitgeist of the moment, or you see something you just can’t let go of and want to post about, that’s amazing. That practice of writing and posting is what will remind you, “oh, I have an idea, I should post that,” as opposed to just talking about it with your spouse over dinner, or kvetching about it to your colleague over Slack. We have a million ideas a day, most likely, and probably a handful of them could make great posts if we were oriented toward a channel.

Eric Ressler [00:19:15]: Yeah, let’s break that down a little more, because what I’m hearing is that you need a little bit of both. You need some amount of structure, because you used the word “practice,” and I think that’s a really good word. The other word I’d use is “muscle.” It is a muscle, and there’s a certain amount of it that’s just doing the reps: A, to get faster at it so it’s not as big an impact on your schedule as an executive, and B, because you’ll actually make better content doing it that way. Yes.

Saralynn Finn [00:19:45]: And I’m going to add a C.

Eric Ressler [00:19:45]: C.

Saralynn Finn [00:19:45]: C: to quiet the chatter, the “no” in your mind, to give you the confidence to be like, “shhh.”

Eric Ressler [00:19:55]: Yeah, totally. There’s science to back that up. One practice I’ve become familiar with is, upon waking, doing a stream-of-consciousness journaling to get the noise out of your brain. I think that’s a great hack or tip: when you’re like, “what should I post about,” have a scratchpad of idea seeds that live with you, whatever, your Apple Notes or an app, “this might be a podcast episode” or “this might be a post one day.” What usually happens is you come back to those ideas and you’re like, “wow, all of these are... except that one’s actually really good, still. Let’s do that one.”

Saralynn Finn [00:20:35]: Glad I didn’t post any of those. Absolutely.

Eric Ressler [00:20:40]: But let’s break this down: do you need to post three times a week, or every single day? What’s your point of view on that?

Saralynn Finn [00:20:45]: Heck no.

Eric Ressler [00:20:45]: Yeah, okay, good. Glad to hear that. I agree, by the way.

Saralynn Finn [00:20:50]: Yes, okay, good. I think, how often can I offer my audience something valuable? That’s going to vary, it’s going to vary by season, by where your organization is in its process, and by what’s going on in your personal life.

Eric Ressler [00:21:05]: Totally, yeah, I think that’s fair. That gives me a little permission to be less active than I have been in the past.

Saralynn Finn [00:21:10]: Anything you’ve done is better than doing nothing. And that’s a bar, maybe eventually you want to raise the bar for yourself. But I think who I’m speaking to is the executive director who puts all of their energy into their program, and has none left to cultivate their identity or reputation as a thought leader, or as someone who’s a connector publicly. And that’s why the encouragement of our workshop was to uplift other people’s ideas, because that’s the fastest way for both of you to become visible and then get that support.

Eric Ressler [00:22:10]: Yeah, I love that. One of the things I’m reflecting on as you say that is, we have our Spotlight series where we do interviews with social impact executive directors and leaders on this show. I love posting those because it’s like I get to post something that’s not about me, and the people I choose to interview are people I’m genuinely interested in learning from and sharing their perspective. Those posts are such a joy for me because they relieve that pressure. I have other posts I do as well, and I’ve been significantly less consistent than I have in the past, I can break down why in a bit. But I want to make something really important clear: a clear distinction between are we talking about brand pages on LinkedIn, or personal pages. Should it be the ED? Should it be the comms director? Who should be posting, and in what way?

Saralynn Finn [00:23:00]: That’s a great question. Personal pages have the highest likelihood of having your ideas travel far. Unfortunately, the brand page should be, I don’t know, an archive almost. I’d like to just turn them off, I don’t know what to call it. It’s not a place where you’re going to get as much dynamic interaction, which is just how it works, we’re relational beings and our algorithms can’t overcome that as much as we want them to. So it should definitely be on your individual page. If your comms team has the capacity to support this, that’s great, if not, go ahead and do it on your own. I think both your organization’s point of view and your own point of view can exist on your page, and that differentiation is important. Your perspective on the work of your organization is ultimately what people want to hear. It shouldn’t just be a copy-paste, “hey Claude, can you rearrange these words for me” of the post the brand did. It should really be, how are you connected to this? What are you celebrating, if you’re sharing a post from your organization?

Eric Ressler [00:24:35]: I think that makes a lot of sense. Whether it’s the algorithm, or human psychology, or a combination of the two, that’s the kind of stuff I’m personally more interested in, that I find myself engaging with. I don’t want to see the company line, that’s great, if I want to learn that I’ll go to your website and read it. I think it’s important to have a company page that’s accurate and shows it’s alive and real, maybe even reposting some staff content. That’s how we run the Cosmic page, probably not as consistently as we should, and the Designing Tomorrow page, we’re just not investing time or thought into those pages. Everything’s coming through my personal page on LinkedIn, because, to your point, it’s a personal platform. But I think the stories that feel the most raw and human, and I’m not talking about needing to know everything about your personal life -

Saralynn Finn [00:25:35]: Overshares.

Eric Ressler [00:25:35]: Overshares, or trauma dumping, or anything like that. But just give me the raw, uncut stuff that’s like, “hey, this is what we’re struggling with right now, anyone have any tips?” I’d love to see more of that content in the social impact space. “Hey, we tried this intervention and it didn’t go as well as we thought, here’s maybe why, has anyone done something similar?” That’s a tough thing to sell.

Saralynn Finn [00:26:00]: I wish our sector wasn’t as allergic to admitting failure as it feels like we are.

Eric Ressler [00:26:05]: It’s tough though, right, because then donors are like, “do these guys know what they’re doing?” Funders too. But I think that’s a bit of a trap, I don’t think it’s actually true that that’s a problem, as long as you’re smart about how you do it, and again, not oversharing.

Saralynn Finn [00:26:20]: Yes.

Eric Ressler [00:26:20]: Okay, so we’re talking to listeners here, they’re sold, they’re like, “yes, LinkedIn is the place for me.” The time thing is real, if you’re an executive director, let’s say you have a comms team, or even if you don’t. I think this has to be original content from the ED at some level, do you agree?

Saralynn Finn [00:26:40]: I agree. I agree. I think this taps into your point of view on having a point of view.

Eric Ressler [00:26:50]: Yeah, it does. Okay, we’re going real meta.

Saralynn Finn [00:26:50]: Going really meta. You have to be visible in the letters, the characters you’re writing, in the ideas you’re sharing. It can feel like, “oh, am I going to get feedback from my board for sharing something publicly that’s not exactly aligned with my organization?” Of course you’re aligned with your organization, you’re just also a human and have your own take on this, and can share your journey with this topic. You can share how you see this playing out in your day-to-day. Being visible in this is what’s going to move it forward with a broader audience than you might normally reach. That’s what makes it so that when someone gives you an introduction to someone else, and they check out your page, they see, “oh look, this is a human, not just a title.” And I trust that. We trust humans, we don’t just trust someone because they have a title. So the more you can bring who you are to your digital persona, the more that’s going to resonate.

Eric Ressler [00:28:15]: I think that’s a muscle too, because I feel like early in my LinkedIn posting, and even early in the podcast content we were doing, I felt this pressure of, “I need to be an expert, I need to share expert tips.” More and more, I think it’s really about, “here’s what I’m thinking about, here’s what’s interesting me, here’s observations and things I’ve learned,” not trying to make everything a teachable moment necessarily unless it really is one and I want to share that. What’s your take on that?

Saralynn Finn [00:28:50]: I’m going to use the word I think everyone’s tired of, but authenticity, it matters. People can feel it instantly.

Eric Ressler [00:29:00]: And you can feel it when you’re not being authentic. I’ve typed stuff and thought, “is this me?”

Saralynn Finn [00:29:05]: Cringe.

Eric Ressler [00:29:05]: And that’s always a bit of a struggle.

Saralynn Finn [00:29:10]: Yeah, and I think that’s probably the most time-consuming part, right? “Here’s my idea, this is what I want to share,” but then, how do I bring myself, my professional self, my personal self to it in a way that feels authentic? But that’s ultimately what thrives. I think the more folks in our space get used to this, the more we’re going to make our comms teams’ lives easier, because I see so often where the personality gets sanitized out of the brand voice, or we want to work with a collaborator, an influencer, a surrogate, and the process is painful to get to a yes on messaging that feels authentic for them and stays within the brand guardrails. The more executives get used to showing up visibly in their work, the more it’s going to ease the way for more successful communications, because diversity in voices, everyone singing in the choir at different levels, is what the future of successful communications looks like.

Eric Ressler [00:30:30]: Yeah, I think that makes a lot of sense. Like a lot of things in comms, I always feel individual political campaigns are a little bit ahead of trends in communications, sometimes in good ways, sometimes not. But there’s been this huge sector-wide learning coming out of the last election cycle, that candidates need to be real people, they can’t just be packaged versions of the party line. When you see candidates winning, we’ll throw out Mamdani, one of the reasons he’s been so successful is because, whether or not you agree with his politics, I believe that guy is legit. I believe he cares about the things he says he cares about, and he’s bringing his whole self into his campaign. Political campaigns and candidates are always a step ahead of social impact campaigns and comms, in my opinion, in my experience. I’m seeing a lot more of that start to happen for social impact organizations, that maybe for a long time were humming along just fine, the executive director wasn’t a household name, and funding was flowing. Now we’re in a very different ecosystem from a media standpoint, a digital standpoint, and a funding standpoint. I don’t think it’s going to fly anymore.

Saralynn Finn [00:31:50]: Absolutely not. I’m so excited to see the trend of executive directors really putting themselves out there and, beyond just the ED, program officers or impact leaders within specific issue areas are more and more putting some energy and thoughtfulness into how they show up on behalf of their organization, but also on behalf of their cause.

Eric Ressler [00:32:20]: Yeah, 100%. I think another thing I’d like to reflect on as we work toward wrapping this up, and I’m saying this out loud almost for myself, but also for our listeners: I think LinkedIn especially is a platform where you kind of get out of it what you put into it. Yes, there’s trash on LinkedIn, there’s AI slop, there’s negativity and hate, it’s not a perfect platform. But what you actually interact with and put out into the platform is what you’re going to get back. I’ve met incredible people because of being on LinkedIn who are dear friends of mine, colleagues, and collaborators, and that worked because I posted, I had things that resonated, and I slid into their DMs, and we got to actually meet, and then meet in person.

Saralynn Finn [00:33:15]: There are people out there looking for you. They want to find you, and you need to give them a signal to find. This humility does not require invisibility.

Eric Ressler [00:33:25]: Yes, that’s amazing. That’s our episode title right there.

Saralynn Finn [00:33:30]: So you’re just there, being your little beacon of you.

Eric Ressler [00:33:35]: Yeah.

Saralynn Finn [00:33:35]: I’m thinking of sonar, boop. Boop. Boop. Okay, maybe sometimes your frequency goes boop, oop, that’s fine. But the LinkedIn algorithm has a longer cadence than all the other platforms. Your post doesn’t actually reach its maximum impressions or views until about three weeks. It takes a while to understand what signals are working, and your post has a pretty long lifespan. If people are commenting on other folks’ posts, or your friends are commenting on your post, that extends the timeline for the reach of your post up to, I’ve seen, about two months. Some posts that come up in my feed are about two months old, and I’m always like, “oh, hi, this is actually not topically relevant to the world we live in anymore, because we’re in a new war or something else,” or whatever tragedy is happening, or something else has happened. But, oh cool, okay, good to know. And then I see, oh my gosh, the comments are alive and happening, that’s why this has happened. LinkedIn absolutely prioritizes your profile based on your comment activity too. So if you’re afraid to get out there and put yourself out there at first, maybe just dip your toe into the comments.

Eric Ressler [00:35:00]: I think that’s a great place to start, and for the episode, I think a great place to end. Saralynn, this has been awesome. We could go on forever about posting on LinkedIn, but hopefully this inspires some people. It’s inspiring me to get back in the game a little bit.

Saralynn Finn [00:35:15]: Awesome. In a way, can I offer your viewers and your audience, we’re doing a LinkedIn peer support learning group that I’m leading and helping to facilitate, kind of based around the workshop we did at the Forum. Hopefully Eric can put it in the show notes or on the webpage or something, and I’m happy to have your folks jump in to get some support on this. We’ve all been boosting each other’s experiments.

Eric Ressler [00:35:30]: Awesome, very cool. That sounds like a great way for listeners to get started. Saralynn, thank you so much, it’s been awesome.

Saralynn Finn [00:33:40]: Thank you.

Eric Ressler [00:33:45]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment, it really helps. [00:36:00] Thank you, and thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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Every social impact leader believes in their mission.

Funders assume that too. What they actually want to know is why you, specifically, over the ten other orgs working the same issue, or the bigger name with more reach and a longer track record.

Most leaders answer with passion, good programs, being impactful. Genuine things that still don’t add up to a strategy.

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In this episode, Jonathan and I dig into a framework we use with clients constantly: naming your organization’s exact role inside a broader social impact ecosystem, specific enough to defend, credible enough to believe, and clear enough that funders, staff, and partners all describe your org the same way.

The framework itself is simple to describe and hard to actually do: map who else is working your exact issue, get honest about where you’re uniquely positioned inside that field, and build a story you can defend when someone pushes back on it.

Jonathan brings Seymour Center into it as a live example, working through the question in real time. You’ll probably recognize your own org somewhere in his answer.

Episode Highlights:

[00:00:46] Why differentiation is the one thing social impact leaders don’t spend enough time on
[00:01:24] Every organization has a role to play in a broader social impact ecosystem
[00:02:28] What nonprofits can learn from how B2B and B2C startups think about differentiation
[00:03:25] Why “we do good work” isn’t enough to win over savvy funders
[00:04:45] Jonathan’s own evolving answer to what role Seymour Center plays in Santa Cruz
[00:06:38] The vague language and buzzwords that quietly sink an organization’s positioning
[00:09:24] Why believability matters more than boldness when claiming a role
[00:17:18] How passion becomes a brand story, and why that’s a trap
[00:19:44] Finding the “core durable truths” that define an organization’s identity
[00:21:24] Mapping the ecosystem: the first exercise Cosmic runs with every client
[00:22:14] Getting brutally honest about strengths, weaknesses, and what should stop [00:27:41] The moments that call for revisiting your role, from new leadership to ecosystem disruption

Notable Quotes:

[00:19:20]: “Passion is not a strategy. It’s not a position. It’s not a role. We can’t compete on being the most passionate, because who’s going to claim otherwise?” Eric Ressler

[00:04:55]: “One of the decisions I made pretty early was to align more with the environmental work in town, rather than the other museums, and position ourselves as an amplification force for the environmental work happening here.” Jonathan Hicken

[00:06:25]: “People get about 70% of the way there, but they don’t do the hard work of getting the rest of the way. It looks like vague language about describing who they are. It looks like buzzwords that sound good but confuse people.” Eric Ressler

[00:17:45]: “Someone’s like, I love the ocean, I want to save the ocean, so we’re going to create a museum to save the ocean. But that’s the vagueness we’re talking about.” Jonathan Hicken

[00:24:35]: “The better you can be about naming and claiming your role in the ecosystem, and doing that with conviction and clarity, the better you’re going to be at attracting the fundraising you need, the team you need, and the internal strategic clarity to make the right choices.” Eric Ressler

[00:23:00]: “That’s how organizations get stuck for decades. They’re usually aware of their ecosystem, they’re just not willing to act on it.” Jonathan Hicken

Resources & Links:

• Seymour Marine Discovery Center: Jonathan Hicken’s organization, used throughout as the working example

• The Nature Conservancy: mentioned as an example of a large, well-established environmental org

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:35]: Jonathan, there’s something that I wish social impact leaders and social impact orgs spent a lot more time thinking about than they do. There’s actually a couple things, but for today’s episode there’s one thing I want to focus on, and that is, call it what you want, I’m going to call it differentiation. Let me go into some detail around that, and I’d love for you to grill me on this and poke holes in my thinking.

Jonathan Hicken [00:01:00]: That’s my favorite thing to do.

Eric Ressler [00:01:00]: That’s like what the show is, right? So here’s how I think about this, and I have a better metaphor that I use that seems to make more intuitive sense to folks. I’m going to make a claim here: if you are doing work in the social impact space, especially if you’re doing work that is systems-level, big, intractable work, you are part of a social impact ecosystem. There are many players in this space, collaborators, maybe sometimes competitors. There are forces working against your issue at times, and it’s a complex, moving, fluid ecosystem. The way I think about this, and that I wish more people would think about it, is that you need to be able to clearly name and claim your role in that ecosystem.

Jonathan Hicken [00:01:45]: For who?

Eric Ressler [00:01:45]: For yourself, as an organization, and this will connect the dots a little bit for the people you need to power your mission, whether that’s funders, staff, supporters, or volunteers.

Jonathan Hicken [00:01:55]: I mean, I think this is something I actually think a lot about right now, with Seymour Center as a museum and sort of one of these public spaces, but also as an environmental organization. I think a lot about how we’re positioning ourselves within this whole ecosystem and the different categories we might fit into. So I think it’s a valid thing to dig into today.

Eric Ressler [00:02:15]: So I’m going to do something that I know nonprofit people love, and I’m going to compare them to not-nonprofit organizations. My background early on was working in Silicon Valley with B2B startups and B2C startups, and those folks think about this every day, right? Even before they go to market, it’s like, how are we going to differentiate within the market?

Jonathan Hicken [00:02:35]: Yeah, I was in B2B SaaS for years, and every executive meeting had that theme in it.

Eric Ressler [00:02:40]: So we’ve got two white dudes talking about B2B SaaS. I’m now bald, which is even better. Now we don’t just have a two-white-dude podcast, we’ve got one of them being bald. We’re just checking all the boxes.

Jonathan Hicken [00:02:50]: I have two podcasts.

Eric Ressler [00:02:50]: So you’ve got two. All right, okay. So all that to say, I still believe, and I wish more people would spend time in the social impact space thinking about this. The reason is, I think it’s too easy to gloss over. We get stuck in this mindset of, well, we’re doing good work, our programs are successful, we’re impactful, maybe even we’re doing pretty well from a fundraising standpoint. But I say, not enough. And I also say, usually if you haven’t done this work, those first few things are likely not to be true. So when you go into a potential funder meeting, one of the things the funder is going to be asking is, why support you? A lot of times folks in this space think about that as, why support me, what’s my credibility? But I actually think most, especially the savvy funders, are thinking about why you’re the right fit to solve this problem against other people also working on that problem.

Jonathan Hicken [00:03:50]: This is interesting, because I do a lot of the fundraising, major donor and foundation work, and I often think about myself as a philanthropic matchmaker.

Eric Ressler [00:04:00]: Yeah. Exactly.

Jonathan Hicken [00:04:00]: Where I’m like, I just want to match this funder with whoever’s going to do the work that delivers the most impact. There’s some genuine authenticity to that, where it doesn’t matter if it’s me. But also, if I don’t have a good answer to why their investment in me might have more of an impact, or the kind of impact they want, than somebody else in the ecosystem, then, brass tacks, I might lose out on that opportunity to bring in funding.

Eric Ressler [00:04:30]: Yep. Actually, I’d love to ask you: as you’ve been evolving your leadership and your position within the broader social impact ecosystem here in Santa Cruz, and in the environmental and climate space, how do you think about naming and claiming your role? Have you thought about it from that perspective before?

Jonathan Hicken [00:04:45]: Yeah. When I first started, Seymour Center was viewed as one of the museums.

Eric Ressler [00:04:50]: Yeah, one of the museums in Santa Cruz.

Jonathan Hicken [00:04:55]: One of the museums in Santa Cruz. And one of the decisions I made pretty early was to align more with the environmental work in town, rather than with the other museums, to position myself as, hey, we are an amplification force for this environmental work happening here. Although lately I’ve been thinking about whether we should position ourselves more as a science communicator, as opposed to environmental work. So this is a question I’m actively toying with.

Eric Ressler [00:05:20]: And all of those are role-based questions. Are we playing the role of a museum? Are we playing the role of environmental org? Are we playing the role of a communications org?

Jonathan Hicken [00:05:35]: Well, I mean, there’s role, but I also say it’s sort of like our position in the ecosystem. Because in each of those ecosystems we could occupy or claim a particular spot within it. Within the museum space, we could be the science museum. Within the environmental space, we could be the storytellers. Within the science communication space, we could be the local solutions amplifier. So in each of those ecosystems, we would play a role. But yeah, this is a question I’m thinking about literally this week.

Eric Ressler [00:06:10]: The reason why I think this is so important to spend time thinking about, if you’re a leader in this space, is because it’s kind of this upstream unlock that makes all kinds of other decisions a lot easier. And here’s what I’ve noticed: people get 70% of the way there, but they don’t do the hard work of getting the rest of the 30% of the way there.

Jonathan Hicken [00:06:30]: Well, what is that?

Eric Ressler [00:06:35]: What does that look like? It looks like vague language about describing who they are. It looks like glomming onto buzzwords that sound good but kind of confuse people. And what that means is you end up being able to justify all kinds of activities, investments, and partnerships that are not in your sweet spot. So another way to think about this is: what is our sweet spot as an organization? Where are we at our best? Where are we uniquely positioned to make the biggest impact, given the constraints, given the state of play, given our skill set, given our background? A lot of times when we’re helping orgs through this, we go all the way back to the origin story. What’s the core part of your DNA as an organization? Who even are the founding team? Because a lot of times, even for orgs that have been around for quite a while, that DNA carries through in the culture, in the skill set, and in who they hire into, and what the team members are actually well-versed and good at. I’m not saying you should never pivot, or grow, or upskill. But what I am saying is that you need to have a very clear sense of what your sweet spot is.

Jonathan Hicken [00:07:40]: Let’s unpack the implications of doing this well versus doing this poorly. So, you alluded to one already: are you missing opportunities to bring in funding? Where my mind goes on that is, maybe if you don’t have a good sense of your spot in the ecosystem, you’re talking to the wrong funders.

Eric Ressler [00:08:00]: Might be talking to the wrong funders, yes.

Jonathan Hicken [00:08:00]: They may be interested in a very specific piece of the work that you might actually do, but if you’re not able to articulate that that’s your role in it, then you might miss out on that partnership.

Eric Ressler [00:08:10]: So that’s one flavor.

Jonathan Hicken [00:08:10]: Yeah.

Eric Ressler [00:08:15]: Another flavor is you’re talking to the right funders, but they don’t know it, and you don’t know it, in the sense that you can see a potential there, but you don’t ever quite get over the finish line. You have a lot of conversations, and those feel good, but you never get the check, or you get a check that’s a third of what you wish it could be, because there’s not enough clarity around what funders want, which is confidence and clarity that their investment is going to lead to an impact, in the best case.

Jonathan Hicken [00:08:40]: So one of the things that goes through my head, in my executive director role, is I have to find this balance between painting this big vision, painting this big reason why our work matters. The risk in doing that, of course, is that you go so big or so vague that you lose the clarity in what impact you’re actually delivering, and what your role in that ecosystem is. The risk of going too small is, well, that problem doesn’t sound like it matters too much. So for you, where do you draw the line, in terms of claiming your spot in the ecosystem, when it comes to the spectrum of the size of the problem?

Eric Ressler [00:09:20]: There’s a framing art there, I’d say. It needs to be rooted in truth, at just a baseline. I’m not suggesting listeners take away that they should go find the biggest, boldest way to tell their story and stake a claim, because there’s a believability element to this. This especially becomes relevant if you’re working on a complex, systems-level problem, where the solution or the desired future state is this major thing that’s going to require multiple organizations, public-private partnerships, sometimes even multiple states or communities coming together to solve. So what I’d say is, it needs to be rooted in truth, and the story can go something like this: hey, we envision this kind of world, don’t you also, funder, or whoever we’re talking to? Yes. Well, we see one problem in us getting there is this particular thing, and we tend to be really good at that. That’s our focus. We believe X, Y, Z, and this is the solution to that. There are other partners that matter in this, and by the way, we’re doing this cool initiative with that partner who’s really good at this thing. But this is the thing we’re uniquely positioned to do. And we need to make a case, and now we’re kind of coming off the dialogue here for our listeners, we need to be able to make a case that this part matters, it’s important, and it’s distinct enough that we can make a meaningful, believable claim that we’re positioned to do that part better than anyone else.

Jonathan Hicken [00:10:45]: So it’s actually not, my framing of this, the size-of-problem spectrum is actually kind of a red herring. That’s not really the way you’re thinking about it. It’s that clarity in your role in the ecosystem actually delivers meaning, delivers weight, delivers a sense of real possibility in the impact.

Eric Ressler [00:11:05]: I think that’s right. And the scale of the problem is highly dependent on what kind of org you are. Even to use Seymour Center as an example, you’ve made a strategic choice to draw lines around Monterey Bay and Santa Cruz specifically, to a degree, the scope and scale of your focus as an organization.

Jonathan Hicken [00:11:25]: On your shirt right there, that is literally the scope of what we’re doing.

Eric Ressler [00:11:30]: Science, Solutions, Santa Cruz. For people who are listening. So thanks for the shirt, by the way.

Jonathan Hicken [00:11:35]: You’re welcome. Looks good on you.

Eric Ressler [00:11:35]: So it kind of fits, right? We’re like, hey, okay. So in that way, though, you do have impact outside of this role you have here, but that’s part of your sweet spot. It’s one element, one ingredient in how you claim and name a role within a broader ecosystem. You’re saying part of that is our region, a regional focus, which can be totally legit.

Jonathan Hicken [00:12:00]: You brought up this idea of, or alluded to a moment ago, the other players in the ecosystem. And I think what’s unique about social impact, versus the private sector, is that it’s actually important, I believe, to be in dialogue with the other people in the ecosystem. Because those funders are talking to everybody.

Eric Ressler [00:12:20]: Yep, 100%.

Jonathan Hicken [00:12:20]: And if, in talking to everybody, they don’t actually put the pieces together for your role in it, you have this risk of being less credible, because you don’t exist in a vacuum in these funding conversations. So you need to make sure, in some ways, that your partners in that ecosystem are also bought in to your role in it all.

Eric Ressler [00:12:45]: Yeah, which I think is an interesting distinction between the private sector and the social impact sector: we’re not really competitors. Even if we’re competing for money, we’re all ideally working toward the same thing. There are exceptions to that, when you’re on different sides of an issue, anti-climate people or anti-whatever issue.

Jonathan Hicken [00:13:05]: That’s a good point.

Eric Ressler [00:13:05]: But when you’re talking about allies, let’s use that term, I think a good heuristic is to ask: what if the funder I’m talking to also talks to everyone else in our space? What are we going to say that everyone else is also going to say? Great, might not even be wrong. But how can we help a potential funder or supporter make the best decision? That might even sometimes be, well, we need to fund the Seymour Center and this other org, because they’re intersectional, or because they’re collaborative, or whatever it is. But it’s a more compelling story, a more honest story, and a more persuasive story when you can say, this is the thing, this is the role we’re best at, we’re uniquely qualified for. It takes you out of this mode of trying to impress, talking yourself up. All that matters too. You want to be good at impact storytelling and having credible proof points. But if you have this framing of being clear and convicted about your particular role, and you can tell that story to a potential funder, I think it’s a way more powerful story.

Jonathan Hicken [00:14:15]: I have some theories about why we don’t always—

Eric Ressler [00:14:15]: Always do that

Jonathan Hicken [00:14:20]: —do this. But from your seat, having talked to however many dozens of organizations you’ve worked with, why do you—

Eric Ressler [00:14:25]: Hundreds.

Jonathan Hicken [00:14:25]: Yeah, why do you think that happens? Or what do you think is the main block for an organization going where it needs to go?

Eric Ressler [00:14:35]: What I’ll say is, this isn’t a universal problem, but it is a pretty persistent one. I see this pattern a lot, and I see it with orgs that are new, and with orgs that are, by many metrics, pretty successful and have been around for a long time. For the new orgs, I feel like it is, or maybe a new chapter of an org, it’s an uncertainty. It’s an unprovenness. We don’t actually know what our role is yet, we’re still figuring that out, here’s what we’ve done in the past, even maybe on different teams, we’re starting this new org, or the space is changing so we don’t quite know what our role should be, or maybe the role it was is no longer relevant. And for orgs that have been around a long time, what often happens is they start to see the full intersectional scope of the problem, and they try to solve more and more of it. I think that can sometimes work, if you’re a big enough org, and you break it down into divisions with multiple teams, where you’re almost like a federated, multidisciplinary org with unique teams for unique portions of the role. So you also have to have a litmus test: for the size org you are and the level of ambition you have, and the scale and scope of the problem, is it credible for you to claim that role? Because at some level, it has to pass that litmus test. A savvy funder is going to be like, okay, you’re an X-million-dollar-a-year org in this space saying this is your role. Does that pencil out? Does it pencil out for me? Do I believe you can do that?

Eric Ressler [00:16:20]: Hey friends, real quick before we continue today’s episode: I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last fifteen years, we’ve helped leaders like you nail your impact story and sharpen your strategy. But we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:17:05]: I have a theory, and it’s kind of the other side of the coin for what I think makes the social impact space special, which is that we, executive directors, all of us who work in this space, often approach the work because we care. It’s that passion piece. This is what makes it so powerful. And I also think the other side of that coin is that passion can sometimes become the brand story, where it’s like, just to use Seymour Center as an example again, and this isn’t speaking about me, but hypothetically, someone’s like, “I love the ocean. I want to save the ocean. So we’re going to create a museum to save the ocean.” But that’s the vagueness we’re talking about, right?

Eric Ressler [00:17:55]: Well, and also, believability is a factor. A low-millions-of-dollars-a-year org in Santa Cruz, positioned to save the ocean? No, no. No org is positioned to save the ocean. That’s a ridiculous claim. Now, you can have a vision for what the world looks like if you and other players in your ecosystem are wildly successful. Great, tell me about that. What could our ocean system be in ten years, instead of the doom-and-gloom narrative we hear? Okay, I’m on board with that, as a funder. I want that too. I care about the ocean, I want to save the ocean at large, I happen to live in Santa Cruz or have some connection to you. So, Jonathan, what’s your role in that? Exactly. That’s the next logical question. How do you create impact, and why are you the org I should fund instead of the Nature Conservancy, or some other big-name org more credibly suited to take on a bigger piece of that puzzle?

Jonathan Hicken [00:18:55]: But do you think this passion thing is maybe what takes us down the wrong path in our storytelling?

Eric Ressler [00:19:05]: Yeah, I think that’s a pervasive element in this space, and I think it’s a good thing overall, as long as we think about it in the right way. I think passion is a powerful force, and not one we should try to snub—

Jonathan Hicken [00:19:20]: —diminish. Or diminish.

Eric Ressler [00:19:20]: But passion is not a strategy. It’s not a position, it’s not a role. We can’t compete on being the most passionate, because who’s going to claim otherwise?

Jonathan Hicken [00:19:30]: Right. This exercise we’re doing now is essentially the exercise we invite listeners to go through. What is that passion? And then drill down through all these steps and answer all these questions.

Eric Ressler [00:19:45]: So, for listeners who are saying, okay, I buy your argument, Eric and Jonathan, I need to figure out what my role is, now what do I do? I’d encourage people to look at their core, depending on the size and stage of your org, caveat, caveat, but what are those core elements, those core durable truths about your identity, individually as a leader and at an org level, that will always be true? This is something I think about a lot as we do our own brand strategy work for Cosmic. I always come back to, what will always be true, no matter what we do, about our organization? There will always be some kind of design element to what we do, no matter how much deeper we go on strategy, no matter how we change our operating model, our engagement model with clients, design and design thinking. That mindset will always be part of, and true to the core of, how we do our work. So that’s one example for me. For you, it may be some of your beliefs around place-based change, or, based on past discussions we’ve had, what else comes to mind for you?

Jonathan Hicken [00:20:50]: Yeah. We have a beautiful building on the ocean. That will always be true. We exist in Santa Cruz. That will always be true. So these are just some of the things that would be the core truths for us.

Eric Ressler [00:21:00]: So distill down to some of your core truths about the elements of your identity and organization that are durable, that will always be true, or at least for the foreseeable future, will always be true. Start there and build off of that. Then be real honest. When we do this positioning and brand strategy work for clients, one of the first things we do is map the ecosystem. We ask, who are the other collaborators, credible players in your space? We like to look above and below in terms of size. We literally map this, on a four-quadrant, or x-y, axis. Part of it is, how do we frame even that axis, what’s the x and y lines on these graphs? That in itself is a strategic choice, because there are limitless ways to make a graph like this, and some of this becomes performative if you’re not careful. But map the ecosystem, and be willing to be brutally honest, because if you want this work to actually make a meaningful difference, and not just be an exercise you check the box on, you have to be willing to be brutally honest about your strengths and weaknesses.

Jonathan Hicken [00:22:15]: And to be clear, when you talk about brutally honest, where my mind goes is, I have to look at my organization and identify what’s working, what’s not working, what are we uniquely good at, what are other people doing. And then the next thought, from an executive director’s chair, is, what does that mean for my people?

Eric Ressler [00:22:30]: What does that mean for my people?

Jonathan Hicken [00:22:30]: Yeah, honestly, that’s where it goes, because if I’m being brutally honest, what I’m thinking about is programs that should or shouldn’t exist.

Eric Ressler [00:22:40]: Sometimes it’s that—

Jonathan Hicken [00:22:40]: Right?

Eric Ressler [00:22:40]: —or people who need to be upskilled, or who maybe aren’t a good fit, once you have that clarity. But as much as that can be difficult from a leadership standpoint, avoiding it is not a good strategy long-term either.

Jonathan Hicken [00:23:00]: Oh, absolutely not. No, that’s how organizations get stuck for decades on end, because they haven’t made those changes, maybe they’re aware of—

Eric Ressler [00:23:05]: They usually are.

Jonathan Hicken [00:23:10]: Yeah, their ecosystem, but for whatever reason, they’re not willing to act on it.

Eric Ressler [00:23:15]: I’ve seen different versions of this, but back to the brutally honest example: is it the people, is it the programs? I think brutally honest really means being clear-eyed about where you’re actually, tangibly, measurably making an impact, and where it’s more aspirational, and where you are on the trajectory of your vision. Because usually you’re midstream on some strategic plan or growth plan, and you need to be brutally honest about what’s truly in your sweet spot and what’s starting to be on the outskirts of that. I’m not saying you need to focus down to doing one thing perfectly. Sometimes that’s a good strategy, sometimes it’s not. I think about it like a bullseye: what’s in the absolute middle, what’s in the first ring, the second ring, and what’s off the board. You need to make a choice as a leader around how big of a bullseye you draw, and how big of a board you’re drawing. But to me, mapping the ecosystem is the first step, so you can compare who else out there can make these claims, and whether that claim is more or less true or credible. Because often in this space, a lot of people are making the same kind of claims. You’ll know, if you’re in the space, what’s real and what’s not. Funders may hopefully get to that point too, but it’s not guaranteed. So the better you can be about naming and claiming this role in the ecosystem, and doing that with conviction and clarity, the better you’re going to be at attracting the fundraising you need, the team you need, and the internal strategic clarity to make the right choices around what moves you make as an org.

Jonathan Hicken [00:24:55]: All right, so we’ve got being aware of and being brutally honest about your core strengths and weaknesses. We’ve got mapping the ecosystem. What’s left?

Eric Ressler [00:25:00]: So, if you have those two ingredients, you’ve got at least a pretty good start. Now you need to craft some kind of narrative that goes something like: because we have these core strengths, we can claim this role in the ecosystem, and because we can claim that role, that helps the cause at large, because X, Y, Z. That’s terrible messaging, but logically, you need to be able to tell some kind of story like that.

Jonathan Hicken [00:25:30]: And I’d say then you actually need to go road-test that. This is where you’d go to the people in your ecosystem, and directly or indirectly, pressure-test it. Is this different from them? Does this accelerate what they’re doing, or does what they’re doing accelerate what I’m doing? Do we have that positive feedback loop?

Eric Ressler [00:25:50]: Yeah. So now let’s talk about how you know if you’ve chosen right, or if it’s working. How do we measure this when we do this work with clients? None of this is a breakthrough on its own, but it still leads to breakthroughs. What I mean is, we’ll literally interview, we do 360 interviews with leadership and stakeholders closely tied to the org, board members, partners, and ask, what is this org’s role in the space? We look at how much coherence there is in those answers. This data is going to be messy, some people are going to have a weird, zany answer influenced by their own perspective, no matter how good you’re doing as an org. But you start to see patterns emerge, either a coherent picture or a complete scattershot, or somewhere in between. When you start to map those, you should see some kind of pattern forming. We’ll also run basic surveys with supporters: how do you think about the org, what do they do, what’s their focus, why are they different than other people, we do this all the time. And the answers we get can be so insightful, because you can see how people are perceiving you as an organization. Here’s a caveat: if they’re not perceiving you well, is that because you haven’t done a good job strategically at naming and claiming a role in your ecosystem, or is your messaging, your communications, or your distribution of that story broken? Both can be true, or either can be true. So watch out for that, to our listeners.

Jonathan Hicken [00:27:25]: How would you rank this, going back to our strategic tier ranking? When do I do this, and is there ever a good, better, or bad time to be doing this exercise?

Eric Ressler [00:27:40]: Anytime you’re making major strategic choices as an organization. Let’s talk about what some of those moments might be: a new executive director coming in, a major milestone, any kind of transformational or pivotal point, a new strategic plan, a strategic plan being sunset, a new one being built. Anytime you’re making big moves or big choices, it’s worth checking in on this. Is this still our role in the ecosystem? Should it be? The other thing I’d point to is, did the ecosystem get disrupted? Everyone in the world right now, in one way or another, if you’re in this space. Is the funding landscape different? Is the issue landscape different? Anytime there’s a disruption to the state of play, it’s worth double-checking, is this still the right role for us to play? You have to use your common sense and best judgment, because I don’t recommend you pivot this role all the time, or you’re never really claiming it. People get confused: wait, I thought you were this org, now you’re saying you’re this other org. You only get to do that so often—

Jonathan Hicken [00:28:30]: Because—

Eric Ressler [00:28:30]: —part of this is you have to build a reputation. So you have to use your best judgment about when to sit still on this, and when it’s the right time to make a pivot, and how big of a pivot you’re making. But I’d say any of those major strategic moments, either because of internal pressure or external state-of-play change, are worth revisiting this.

Jonathan Hicken [00:29:00]: All right, so what did we miss?

Eric Ressler [00:29:00]: I’d say, if you’re a listener thinking about starting an org, this is, in my opinion, crucial.

Jonathan Hicken [00:29:00]: Yeah, this is kind of step one, almost.

Eric Ressler [00:29:00]: Almost. Should I even start an org? Are there seven orgs already in this space that I should just be joining or supporting? There’s a lot of talk right now about mergers and acquisitions. This is one of the reasons why, there’s frankly a lot of redundancy in the space.

Jonathan Hicken [00:29:30]: And you’re like, I go through that whole exercise and I don’t actually see the role I can claim. Great, okay, let’s merge, or let’s sunset, or whatever.

Eric Ressler [00:29:30]: So I’d say that would be another time, if you’re just starting an org, where you really need to look at this. I feel like this is really important, and you could describe it as positioning, you could describe it as differentiation. I’ve found that the metaphor of your role in the ecosystem is easier for folks in our space to grok, and I think it’s actually a better way of thinking about it. So I’m glad to riff on it with you today. There are other episodes we can link to around some of these topics. But Jonathan, this was fun. Thank you, man.

Jonathan Hicken [00:30:00]: Thank you, Eric.

Eric Ressler [00:30:00]: If you enjoyed today’s video, please be sure to hit like and subscribe, or even leave us a comment, it really helps. Thank you, and thank you for all that you do for your cause, and for being part of the movement to move humanity and the planet forward.

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Sarah Newkirk became executive director of the Land Trust of Santa Cruz County in the middle of a capital campaign. It was her first time leading a full organization, not just a conservation team.

Five years later, she has closed a $15 million farmland deal, opened a wildlife crossing that Caltrans is now replicating statewide, and taken flood-prone farmland out of production instead of walling nature off from the rising sea.

The Land Trust treats wildlife corridors, working farms, wetlands, and coastline as one overlapping mission instead of three separate fights, and that range is the model now.

None of it happened because a plan showed up fully formed. Newkirk’s method was to stop asking why something couldn’t get done and start asking what would have to be true for it to succeed.

Measure Q, the county fund now generating seven million dollars a year for climate resilience, exists because she ran that exact exercise with her board on a measure that had already failed twice.

The throughline across five years of land deals, a rebrand, and a ballot measure is relationships: the currency that actually buys land, wins ballot measures, and keeps stewardship funded for the long haul.

The return on all of it is joy: a staff that loves the work, a public that shows up for it, and a cycle where good conservation earns the kind of community support that funds the next project.

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Episode Highlights:

[00:01:30] Coming in as the new ED mid-capital-campaign, the same week Jonathan started at the Seymour Center

[00:03:00] Learning fundraising by leaning on friendship, not a fundraising department

[00:04:30] The unwritten rule that new EDs get a three-year window, then an expiration date

[00:05:30] Turning the honeymoon period into a five-year strategic plan built around coastal climate adaptation

[00:06:30] Beach Ranch: taking flood-prone farmland out of production to let marshland move inland

[00:07:30] Retiring 47-year-old branding and finally owning the “conservation incubator” identity

[00:09:30] Inside the Highway 17 wildlife crossing, now a model Caltrans is replicating statewide

[00:12:00] Why the land trust model runs on one tool: real estate

[00:16:00] The Land Trust’s three beneficiaries: wildlife, working agriculture, and people, together

[00:26:00] The “what would have to be true” method that turned a twice-failed ballot measure into Measure Q

[00:31:00] Relationships as business model: the Estrada ranch deal and the win-win test

[00:37:30] What disappears without public buy-in: money, momentum, and joy

Notable Quotes:

[00:02:35]: “You can’t even begin to understand the range of things that an executive director of a nonprofit does until you become an executive director of a nonprofit.” Sarah Newkirk

[00:17:15]: “Our third beneficiary is people. Public access is expressly built into our mission.” Sarah Newkirk

[00:24:30]: “Not ‘we need to do this or else,’ but ‘here’s what this could look like if we did it this way.’” Eric Ressler

[00:28:00]: “We made a list of what had to be true, and we made those things true.” Sarah Newkirk

[00:31:00]: “The foundational question is: can what I do as my business model serve you in some way?” Sarah Newkirk

[00:39:15]: “When you provide this kind of conservation work, this kind of climate adaptation work, to the broader public, the public loves it, and therefore they love you. And that is, I think, a beautiful, virtuous cycle.” Sarah Newkirk

[00:39:30]: “I love that the answer is joy. I think we need a lot more joy in how this work happens.” Eric Ressler

Resources & Links:

• Land Trust of Santa Cruz County — Sarah’s organization

• Highway 17 Wildlife Crossing — the crossing project discussed at length

• Beach Ranch wetland restoration — the sea level rise adaptation project

• Conservation Blueprint for Santa Cruz County — the 2012 planning document Sarah references

• Learning the Land podcast — the Land Trust’s own show

• Watsonville Wetlands Watch — stewardship partner organization

• Resource Conservation District of Santa Cruz County — stewardship partner organization

• Central Coast Prescribed Burn Association — stewardship partner organization

• Measure Q — Santa Cruz County’s 2024 water and wildfire resilience tax measure

• Proposition 4 — California’s $10 billion 2024 climate bond

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:01:05]: Sarah Newkirk, welcome to Seymour Studios here.

Sarah Newkirk [00:01:10]: Thank you.

Eric Ressler [00:01:10]: So we are here for Designing Tomorrow, our show about social impact. And I’m really excited to dig in on all kinds of topics. A little bit of background for listeners who may not know you. You are the executive director of the Land Trust at Santa Cruz. And we worked together, full disclosure, on some branding work, and you came in as a new ED. I’d actually like to start there. I’d like to hear your story and your trajectory coming in, having deep expertise and knowledge around conservation and environmentalism, and you can speak to some of the other experiences that you’ve had. But you came in as a new ED to an organization that had rich history, had a lot of community, had a lot of community equity and ownership involved in it. Walk me through what that experience was like.

Sarah Newkirk [00:01:55]: Well, let’s just say that I came in unprepared. I have a rich background in conservation, but conservation practice. I’m a leader of sorts in the sense of building teams to accomplish difficult work. But this was my first experience being a leader of a whole comprehensive organization, including the aspects of the organization that go far beyond conservation: the fundraising aspects, administration and operational aspects, things like fleet management. You can’t even begin to understand the range of things that an executive director of a nonprofit does until you become an executive director of a nonprofit. And when I came in, which was in August of 2021, it was the exact same day that Jonathan became the ED of the Seymour Center.

Eric Ressler [00:02:50]: No way.

Sarah Newkirk [00:02:55]: Exact same day. We celebrate our anniversary every year.

Eric Ressler [00:02:55]: Amazing.

Sarah Newkirk [00:02:55]: And when I first came in, we were actually in the middle, believe it or not, of a capital campaign. My predecessor’s departure came, to some extent, at the expense of that capital campaign, which was well underway. And as you know, capital campaigns are based on relationships, and for the Land Trust, deep and authentic relationships. There’s no way to manufacture those. So the first thing I had to do was get my fundraising legs under me, and I leveraged my friendships to do that. I leveraged my friendship with Jonathan. He helped me write an appeal letter when I didn’t find myself with the staff necessary to do it. So it was definitely a trial by fire coming into that leadership position. But I will say that I was supported by some exceptional staff and some exceptional board members. Yeah, I came in unprepared, but I feel very well prepared now. Five years out, I feel as though I have a pretty clear sense of what I’m doing. They always say that program staff get to be the new guy for about a year, but EDs get to be the new guy for about five years.

Eric Ressler [00:04:20]: I love that. I’ve actually joked with Jonathan before on the show that I feel like a new ED has roughly a three-year window to really put a stake in the ground and prove themselves, so to speak. That’s a weird way of saying it. But I think when a new ED comes in, there’s usually some expectation that there’s going to be some change in the air. And I think there’s this window of opportunity: if you don’t make some of your biggest moves in those first three years, that’s a somewhat arbitrary number, but I’m going to stick with it, you lose your ability to do so. Again, not a strict rule, but I’d be curious to hear, did you think about that coming in, that tension, that balance between wanting to respect what was there and the way things were done, but also knowing that you have your own vision, your own set of opinions, priorities, theory of change? How did you balance all of that?

Sarah Newkirk [00:05:10]: That is absolutely true. And I would add, maybe for later, that I also think EDs have an expiration date. There is a period of time in which you’re going to be effective at making change, doing good conservation or whatever the issue is that the organization’s built around. And then you probably lose your luster after a little while. I don’t know what that period is for me, but I think you’re absolutely right that you have a honeymoon period where you’re this new shiny object that the board has recruited and they’re really proud of, and they’re willing to give you a really long lead. And yes, we took advantage of that, not in a bad way, but we stepped into the opportunity to make big changes, to do things like establish a new strategic plan. We’re working toward the end of a five-year strategic plan that we kicked off in 2022 that brought in entirely new aspects of conservation work the Land Trust had never really done before, including coastal climate adaptation.

Our Beach Ranch project is really the first of its kind, a sea level rise adaptation project where we’re taking marginal, flood-prone farmland out of production in order to accommodate the natural progression of marshland landward as the sea level rises. Doing that also protects farming in the community. That was new stuff. And when we first started talking about doing land deals, and when I say land deals, you have to understand that buying a 250-acre farm on the coast of Monterey Bay is a $15 million enterprise. So I’m not selling a small thing. It’s a big thing that we’re doing. That kind of long lead is absolutely essential. We built that strategy into our strategic plan, but not before we had started to socialize it internally.

Another thing is the branding work we did with you guys. The Land Trust had been represented by pretty much the same collateral since its inception, which was in 1978. It was lovely, but it was dated. We felt that the organization had really turned a corner and was ready to step out into the world as a newer, more modern enterprise doing really cutting-edge conservation. Part of the new perspective I brought to the Land Trust is owning what it already was, which was a conservation incubator. The Land Trust has been, for its entire almost 50-year life, doing really innovative conservation work, conservation work other land trusts don’t do: building trails near farmland, having farmland next to wetlands, doing this wetland regression project like we’re doing at Beach Ranch. And the wildlife crossing on Highway 17, really one of the first of its kind in the state of California. Now Caltrans is replicating that business model in other places to provide for wildlife connectivity around the state.

Eric Ressler [00:08:55]: Could you briefly, just for our listeners who might not be familiar with that project, give the two-minute elevator pitch of what that crossing actually is and why it matters?

Sarah Newkirk [00:09:00]: The wildlife crossing across Highway 17 was built in direct response to wildlife mortality at that exact location. We worked with scientists to find the place where wildlife were experiencing the greatest impact from colliding with vehicles, on the assumption that’s also a place where people are experiencing the most impact from colliding with wildlife. So we had to buy land, or buy an interest in land, on both sides of the highway in order to even get Caltrans started on the process of figuring out how we were going to permit, construct, and operate the wildlife crossing. But since we have, there have been hundreds of crossings: deer, mountain lions, bobcats, and lots of gray foxes. Go to our website at landtrustsantacruz.org and look at the wildlife videos. I know the eagle cams are cool, but the fox videos of those guys transiting, they actually go under there and they play. There are deer that go under there and they take a nap. It’s a fantastic amenity for our community, and an amenity our community contributed to. One of the tools we used to pay for the wildlife crossing was the first Measure D, a transportation bond measure for Santa Cruz County. That really helped spur the fundraising around the wildlife crossing.

Eric Ressler [00:10:40]: I’d like to hold on that a little bit and talk about how you guys think about different levers for creating change. Because working with you, and watching your org since working with you, one of the things that stuck with me is you say you’re an incubator, an innovation incubator, I think is the term you used, right? And what I’ve noticed is you’ve used various methodologies for creating change, whether those are legal interventions or political interventions, like passing Measure D, which gave us a bunch of state funding, or was it state funding that came in as a match? Measure D was local funding. It was all local funding. That’s right. So tell me, when you’re thinking about enabling or enacting your strategic plan, how do you look at all those different tools, those different levers, and choose: these are the ones we’re going to use, these are the ones we’re best fit for. Walk me through your thought process in doing that.

Sarah Newkirk [00:11:35]: Well, the Land Trust model is fundamentally about one tool, and that is real estate. Back in the ‘40s and ‘50s, when there wasn’t such a thing as a land trust, it was the Nature Conservancy that originated this idea: let’s not do the controversial legal stuff, let’s not sue anybody, let’s not do advocacy. Let’s do the thing that is going to be uncontroversial and that is going to protect the resource in the place it needs to be protected the most. And that is to purchase real estate. For years, TNC was receiving gifts of backyards in Connecticut, used to be the joke. The Land Trust of Santa Cruz County also had a similar period of time where what we were doing was basically taking donations. That was what we could afford: free real Estate.

Eric Ressler [00:12:30]: That’s not a bad deal here.

Sarah Newkirk [00:12:30]: And we still own some of those donations, and we kind of wish we didn’t own some of those, but that’s what young organizations tend to have to do. As we’ve grown and our ability to raise money has increased, we’ve been able to prioritize real estate that would really serve the resource best. That’s conservation planning. There’s a whole group of scientists and practitioners who are specialists in this, but the Land Trust was one of the conveners of the group that wrote the Conservation Blueprint for Santa Cruz County. That was written in 2012. It’s still the seminal document we all use for thinking about conservation. It doesn’t contain everything, and when we have to do things like sea level rise adaptation that document didn’t really consider, we have to do an additional plan, but it’s still a foundational document for doing conservation.

But when you get to the point about other tools, Eric, I think we prioritize using tools that will set us up for our other tool better. So obviously we need to raise money to buy land. We also grow relationships in order to buy land, whether it’s with a landowner, or with a partner, or with an elected official who can help direct funding to a project. Those relationships are critically, critically important. And then the other question is: what do we do with the land once we have it? That gets to the long tail of conservation. Everybody thinks about conservation as this discreet thing that happens. You buy the land, you put a fence around it, you stick a sign in, and it’s done. It’s conserved. But it’s not. Our job is to conserve land and then protect those wildlife values, those agricultural values, those public access values in perpetuity. And that’s a super long time. It’s an obligation we take really seriously. It’s a very long-term, noble occupation, the stewardship of land and the stewardship of conservation values. It’s expensive, so we have to raise more money for stewardship. It requires people, so we have to either have people on staff who can do it, or work with partners who can. And we do. We work very closely with organizations like the Watsonville Wetlands Watch, the Resource Conservation District of Santa Cruz County, even the Prescribed Burn Association, all of these partners that help us maximize the conservation value of a property.

Eric Ressler [00:15:25]: I’d be curious to hear your take on the state of play of the broader conservation movement right now. My sense, working with you and observing your work and just paying attention in general, is that there have been some pretty major shifts in how the sector at large thinks about conservation. I think specifically about this glass dome protect versus access, and the deeper meaning between the community and the community’s land and wildlife. What’s your point of view on all of that at this stage right now?

Sarah Newkirk [00:16:00]: It’s a super good question. And it has evolved. I’m fortunate to be old enough to remember how it was done in the early 2000s, and it was very much... I remember conversations at the Nature Conservancy when we were asking ourselves, and the CEO was going around the country asking various chapters, “Should we deal with this climate change thing?” It’s laughable now, right? Because of course it is the thing that is shaping all of our work. But what you’re asking about is something a little different: the role of people and the community in the conservation enterprise. The Land Trust of Santa Cruz County is fairly unique among conservation groups in California in that we serve three specific conservation beneficiaries. One is wildlife and natural resources. The second is agriculture, that our community in Santa Cruz County has a very robust, very progressive agricultural industry. And when I say agriculture, I mean ranching, I mean forestry, I mean row crop agriculture. Our working lands community are big partners. But our third beneficiary is people. Public access is expressly built into our mission. Even if it wasn’t expressly built into our mission, giving people access to beautiful land and nature is the most mind-opening thing you can possibly imagine. If you want to inspire future conservationists, you bring kids out to nature. If you want to inspire gifts to conservation enterprises, you bring donors out to nature. There is nothing more motivating than actually being out there and feeling it, just being quiet for a second and listening to the sounds, feeling the air. Every piece of property is different. It almost has a terroir, almost the experience of being at a conservation property. We are so fortunate to have such interesting places to bring people to. Your listeners should be encouraged to go and become members of the Land Trust. It costs five dollars. You can give whatever you want, but you don’t have to give much. And then you can be invited to all of these extraordinary opportunities to experience these extraordinary places. We have public offerings too, but members get a lot of special treatment.

Eric Ressler [00:18:40]: Well, and if you’re listening from anywhere in the world, a trip to Santa Cruz is never a bad idea.

Sarah Newkirk [00:18:45]: It’s a great idea.

Eric Ressler [00:18:45]: I think that’s something. In our community here in Santa Cruz, there seems to be a nearly universal appreciation, a care ethos around nature. I think it takes a certain type of person to want to live here, or if you were born here, to figure out how to get creative enough to afford to stay and live here. And I think everyone, and this is a bit of a generalization, but most people have some kind of connection to nature, whether it’s because you’re a surfer, or a mountain biker, or a hiker, or an equestrian, or you just like being surrounded by all of this. At the same time, there’s that local perspective that people here have, that I have, even though I’m not originally from Santa Cruz. And then I see these national, international, and global conversations around climate that feel so detached from that experience, where nature is a resource to be extracted, or nature is a thing that isn’t as relevant in our fully digital world. So to your point about getting people into nature: that’s how we create current donors, future conservationists, and even just a reconnection between our humanity and the environment that we all are in, as much as we try to remove ourselves from it. To me, it’s the most important thing to focus on right now. And there’s all kinds of research, I’m sure you’re even more familiar than I am, that the experience of being in nature, the awe you experience, literally changes your brainwaves, literally changes your physiology. Anyone who’s had experiences like that, it’s self-evident. You don’t need to be put in an MRI machine to know that’s true. So I guess my question, after all of this, is how do we connect local conservation and local and individual natural experiences all the way up to global climate change, when a lot of those decisions are being made by global and international climate policy decision-makers who feel like they might as well be as far removed from any individual as possible? I don’t have any access to the UN. On behalf of my clients I do, to some degree, but there’s that sense of: what can I do as an everyday citizen, an individual who cares passionately about this?

Sarah Newkirk [00:21:15]: While it’s a troubling time to be a person in the world right now, it’s not a troubling time to be a person in Santa Cruz County right now. It’s also not a troubling time to be a person in California right now. We live in a community that is really willing, that has an appetite for innovation and for pushing the boundaries of what’s possible on climate action. We live in a state that puts its money where its mouth is. In 2024, California passed Prop 4, the $10 billion climate bond. That bond is now generating revenue for conservation organizations like ours to do the work we do. There’s no place else in the world that supports conservation to the extent California does. Santa Cruz County in 2024 passed Measure Q, the water and fire resilience property tax measure, which is generating seven million dollars a year for public agencies, for nonprofits, for the grant program, so we can all do work that makes our community more resilient to climate change. So I have a lot of reason to hope. To your question of how we connect that to the national scene and the global scene: we need to lean into this kind of thing, to the local. We need to be talking about what we’re doing here, and we need to be convincing people that life is good here because of these investments we’re making.

Eric Ressler [00:23:15]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose-built for nonprofits and mission-driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring your ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters, and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

I love that where you took that. We’ve been talking about this with various guests, and Jonathan and I have been talking about it in various episodes as well, that in the climate advocacy space, especially around climate change, there’s been so much messaging around the potential downsides, and now we’re getting to the point where it’s the realized downsides, right? Coastal erosion, rising sea levels, communities being impacted like today. There’s been very little discussion, narrative change, and visioning around what could be instead. Not “we need to do this or else,” but “here’s what this could look like if we did it this way.” I think that’s a real shame, because I think that’s actually more motivating for an issue like climate action. There are some issues where painting a picture about the downsides makes a lot of sense, maybe to a degree. Public health is a space where that sometimes works, like disease prevention, although that doesn’t seem to be working so well either right now. But for an issue like this, where it’s so easy to tip into apathy, where it’s just like, well, I can’t do anything. The metaphor I’ve used before is it feels sometimes like you’re an ant trying to push a glacier for an issue of this size. My sense is that if instead there was a “here’s what the world could look like, here’s what our community could look like if we were to make these changes, if we were to make these investments instead,” that would be a much more generative, constructive, inspirational, creative act. So why isn’t that happening?

Sarah Newkirk [00:25:30]: I think people get trapped by this “has never been done” mindset, and that leads to the “it can never be done” mindset. I prefer to ask the question of what would have to be true. When we first started talking about Measure Q, it was, one of my trustees came to me on my first day on the job and said, “You know what you need to do? You need to do a local conservation measure.” And I said, “Okay,” because I was too stupid to know—

Eric Ressler [00:26:15]: How hard that was going to be.

Sarah Newkirk [00:26:20]: And so, of course, we had years of conversations about it, and mostly the conversations I was having with stakeholders were conversations about how it couldn’t, that’s been tried before, it’s been tried two or three times before, and we think it can’t be done, it’s never going to happen here. So I had to have a come-to-Jesus moment with my board where I said, “I’m just not sure about this, but let’s brainstorm, because I think that if the following things were true, we might be able to succeed.” If we were able to get a simple majority threshold for victory, we might succeed. If we were able to couch this in terms of the natural world and risk reduction, climate risk reduction, nature protection and climate risk reduction are fundamentally the same thing, or can be accomplished using many of the same tools. And if we’re able to convey that message to the public, they might support something they might otherwise not support. So we did this exercise: what would have to be true in order to succeed, rather than why has this not succeeded? And we answered those questions and we took care of those relationships. Some of the things that needed to be true were that we needed a robust coalition. We needed the Farm Bureau on our side, and they were. We needed a lot of landowners on our side. We needed all of the supervisors on our side, and we got them. So we made a list of what had to be true, and we made those things true.

Eric Ressler [00:28:05]: I just want to underline that strategy to our listeners right now, because I feel like we do something similar when we’re doing visioning exercises on behalf of our clients. I think it’s such a powerful framework, because sometimes going from where you are and who you are as an organization to who you’re becoming, you see where you want to go and you see where you are, and that gap just looks like it might as well be the Grand Canyon. But if you start to break it down into, I’m going to use your words here, the “what would have to be true” for us to be able to get there, you start to tease out the mini steps that get you closer and closer, which can help you figure out: is this viable at all? Do we think we can get seven out of ten of these, or whatever the threshold might be, to get it over the finish line? Do we need to get all ten? So I want to underline that as a brilliant leadership and strategy framework in terms of feasibility of a major initiative, or even just how to break big ambitious problems down into their pieces to be more effective in general. So I want to point out that you talk about this coalition you had to build, all of these people you had to get on your side. I’d love to give you a chance to talk about, you’ve mentioned this a couple times already, relationship building. You talked about it through the lens of fundraising. Now you’re talking about it through the lens of advocacy or politics at a local level. Whose responsibility is that in an organization like yours? Is it the whole org? Is it the ED? How do you think about breaking that down into pragmatic steps that you take?

Sarah Newkirk [00:29:45]: What an interesting question. In our organization, relationships are held by different departments. We have relationships that are primarily about engaging with the public, and we have an engagement department that holds those relationships. We have relationships that are primarily about external, or government, affairs, and we have a department that does that. We have relationships with landowners, and our land protection department does that. We have relationships with scientists and other practitioner partners, and we have a department of conservation strategy and planning. But I think the importance of relationships, and the foundational power it gives an organization to have productive relationships in which each partner is experiencing significant benefit, those are the really useful, productive relationships.

Eric Ressler [00:30:45]: The win-win relationships.

Sarah Newkirk [00:30:45]: The win-win relationships, exactly. And it’s not transactional in the sense of I’m winning, you’re winning, and we’re all winning. It is truly an authentic relationship, because the foundational question is: can what I do as my business model serve you in some way? For landowners, often what they’re experiencing is a crisis of capital. So what we do in purchasing a conservation easement can really help them. We had a land deal recently with the Estrada family, who have a large historic ranch, and there were a number of different family members who owned different portions of the ranch. What needed to happen was it needed to be brought together under the unified ownership of the next generation that was going to operate the ranch. But what they really needed was some funding to operate it. So we were able to come in and purchase a conservation easement that protected the land from development in perpetuity, but also put it in the hands of some very capable and progressive land stewards who are doing an immaculate job of caring for it. We don’t have to do that. But that took a years-long process of building a relationship. What’s wonderful is that now we have that relationship, and we have those partners who are able to speak to their community on our behalf. And you don’t get that unless the relationship is really a productive, mutually beneficial, but also authentic, not strictly transactional, relationship.

Eric Ressler [00:32:40]: I want to spend a little time talking about the relationship with the public that you mentioned, because to me that feels like something I wouldn’t necessarily expect with a land trust. Maybe you tell me, is this a unique flavor of land trust that you are, that does this? Because I could imagine a version of you where this is all behind-the-scenes policy wonk work and real estate work, and the public doesn’t really need to know you exist. You’re just going to do good work behind the scenes for them. But you guys have taken a very different stance, where you’re a very well-known, almost household name in our community, a beloved brand. We experienced this in doing the rebrand, just how much equity and care people had for the Land Trust as an organization, as a brand. Why do you think it is that you’ve set it up that way? Is that intentional? Is that just culturally something you inherited? Why does the public need to know who the Land Trust is?

Sarah Newkirk [00:33:35]: The public doesn’t need to know, but they would get substantial joy from knowing and being engaged with us, because what we have to offer is incomparably beautiful and incomparably valuable. And just as you said, Eric, earlier in the interview, people in Santa Cruz County, on the whole, are here on purpose. The main purpose they’re here for is being able to connect with some component of the natural world, whether it’s the forests, the trails, the surf break, whatever. If you’re not out surfing, you’re at the downtown farmer’s market buying your strawberries for the week. People are here on purpose to take advantage of the resources this incredible county has to offer. So I think people should know about the Land Trust, because we are their representative in making sure that these resources, that make this county so incredible, are able to stay around for the long term and provide all the joy, all the nutrition, all the mental and physical health that comes with being outside, for generations to come. That is, in fact, our mission.

The other thing is that I work with the most incredible staff. We have a staff of about 32 people. They’re mostly about 20 years younger than me, and they are having such an amazing time. I strongly encourage anyone who wants to learn more about the atmosphere of our enterprise to visit our downtown office at 911 Center Street, and just come and talk, come and see what we’re up to, come and look at the map of our properties, come and talk to some of our conservation practitioners, and hear about the work we’re doing to conserve and give access to the public for all of these values we’re protecting. My team is part of what makes the Land Trust the Land Trust, and it’s part of what makes Santa Cruz Santa Cruz. Interacting with the public is something that brings me great joy. It brings my team great joy. And it really is part of the recipe for an organization that can create major conservation impact.

Eric Ressler [00:36:15]: So one of the questions we often ask when we’re doing case for support work for major donors is: what would happen if your organization were to disappear? I actually kind of want to flip that, and I want to press on this one more time, because I’d love you to connect the dots for our listeners. What would happen to the Land Trust and your impact if your public stakeholders were to disappear? I want to ask that through the lens of a belief I have, which is that too many climate action and conservation organizations don’t consider the general public a major stakeholder, especially if they’re grasstops, especially if they’re global advocacy. There’s this kind of, well, these decisions get made behind closed doors, so no one really needs to know who we are. And I don’t believe that’s true. So I’d like you to tell me your authentic answer, whether you agree or disagree with my point of view there. How would your work change if the general public here in Santa Cruz County and beyond were not a major stakeholder in the work you were doing?

Sarah Newkirk [00:37:20]: We would probably still have some lands. I think we would probably primarily be working with conservation easements, where we were able to buy cheap and incomplete. There’s nothing wrong with easements. Sometimes an easement is the right tool for the job. But we would probably be limited to those kinds of conservation agreements, because we wouldn’t be able to afford much else, and because we wouldn’t be able to generate a lot of interest or excitement in doing a full fee transaction. And I say that because, again, it’s these relationships within the community that are generating landowner interest, that let people know there’s an option for their property other than selling it to a developer. I think that if the public were not there, a big component of the vision we have for this county, which is of a thriving, economically viable, recreationally active population that supports conservation because it’s in their enlightened best interest, if you will... I think we would probably still exist. We would be less successful, and we would be fundamentally less joyful. I think the dissemination of hope that the Land Trust’s work brings to the community would also be kind of absent. And I think, Eric, that’s the real story. That’s what the other levels of organization of this country and the globe need to hear: when you provide this kind of conservation work, this kind of climate adaptation work, to the broader public, the public loves it, and therefore they love you. And that is, I think, again, a beautiful, virtuous cycle.

Eric Ressler [00:39:30]: I love that the answer is joy. I think we need a lot more joy in how this work happens. And to your point, that’s already going on right now. So Sarah, before we wrap up, this was so great. Thank you so much. I’d love for you to have a chance to plug anything and everything you’d like. How can people get involved who are here in Santa Cruz County or in California, and how can listeners who are elsewhere in the US or the world, who are listening, what would your advice to them be if they’re interested in conservation and wanting to get involved in their local communities?

Sarah Newkirk [00:40:00]: I encourage all of our local listeners to join up. We have a community, it’s an exciting community. We do all of these events where we’re bringing folks out onto the land to really experience lands that not everybody really gets to connect with. So go to our website, sign up, and become a member. It doesn’t cost very much at all, but obviously we’ll happily receive any contribution folks want to offer. For people outside of our community, take a look at what we’re doing, take a look at what we’re up to. Our website has dozens of videos showing our work in action. There are lots of articles showing our work in action.

Eric Ressler [00:40:55]: You have your own podcast.

Sarah Newkirk [00:40:55]: We have our own podcast, the Learning the Land podcast, that elaborates on the programmatic work we’re doing and the values it’s bringing and protecting for our community. And then tell your own local land trusts the story of the Land Trust of Santa Cruz County: conservation incubator, coming up with new ideas, figuring out what would have to be true and making it happen, because it’s not impossible. There are just obstacles. And let us know what you find out. I would love for it to be an exchange of information, and I would love for our listeners elsewhere in the world and in the country to be able to bring this back home.

Eric Ressler [00:41:50]: Absolutely. So join up if you’re local, or if you’re not. If you are a generous donor and want to see your money go somewhere that’s going to make a real impact here in Santa Cruz, you would be at the top of my list personally. Sarah, this has been wonderful. Thanks so much for joining me today.

Sarah Newkirk [00:42:05]: Thanks, Eric. I appreciate the opportunity.

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There’s a push right now to democratize strategic planning, where organizations survey the community, poll the staff, and put the big calls to a vote, sometimes right down to the budget. The instinct behind it makes sense, but it goes too far.

Your community should have a lot of influence on your strategy. That still doesn’t mean putting your strategy out to a vote. Influence and decision-making power are two different things, and when leaders treat them as the same thing, good orgs freeze.

It plays out in a familiar way. An ED gets so worried about how the community or the staff will react that they can’t make a choice at all, and the whole org stalls waiting for a consensus that isn’t coming.

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All the inputs matter. The leadership team, the community, the data, the gut, a trusted outside voice, peers, the board, the funders. You gather all of it, you look for patterns, and then at some point you stop gathering and you decide, knowing you’ll never have perfect information.

If everyone walks away from that decision happy, the choice was probably too safe. The real wins are the ones where someone disagrees with the path you took and still can’t argue with the results.

Put to a board, it comes down to this: synthesizing all of it into a call only leadership can make, and then owning it, is the actual job. A plan you never execute is worth nothing. The only one that counts is the one you actually run.

Episode Highlights:

[00:00:00] The premise: drafting fantasy strategic planning teams from ten possible inputs
[00:02:00] The ground rules and why every input is assumed to be trusted
[00:02:30] First picks: leadership team vs. the community you serve
[00:05:15] Influence vs. decision-making power, the distinction that runs through everything
[00:07:00] Why fully democratized strategic planning goes too far
[00:08:45] Gut and intuition as a legitimate strategic input
[00:10:45] Data beats opinions, and the difference between predictive and directional data
[00:13:45] The case for a trusted outside consultant or strategist
[00:15:45] Drafting the board, and why boards should support more than they decide
[00:20:15] Peer organizations as input and potential collaborators
[00:22:30] Major funders as another audience you have to serve
[00:25:30] Where frontline staff and public feedback land, and why
[00:28:30] How to actually synthesize all these inputs into a decision
[00:33:00] Win-win as a cheat code, and why pleasing everyone signals a weak choice
[00:31:30] Minimum viable strategy: the only plan that matters is the one you execute

Notable Quotes:

[00:05:35]: “The community should have a lot of influence, but I don’t think this work usually works when it’s truly democratic.” Eric Ressler

[00:11:05]: “We have a saying at Seymour Center here where data beats opinions 100% of the time.” Jonathan Hicken

[00:09:30]: “Sometimes gut level decisions get not as much credit as they should, because the body and the brain are actually really tuned to making complicated choices by intuition at a pretty good rate if you have the right inputs in your daily life.” Eric Ressler

[00:34:30]: “It’s not about finding emotional harmony. It’s a cheat code almost that’s going to unlock everybody’s success.” Jonathan Hicken

[00:33:35]: “If literally everyone is happy, maybe the decision was too obvious and weak and there should have been a little bit more of a bold choice made.” Eric Ressler

[00:32:10]: “You could plan forever, but the only plan that really matters is the one that you actually execute on.” Eric Ressler

Resources & Links:

• Designing Tomorrow Spotlight interview with Rob Acton on designing effective nonprofit boards

• Cause Strategy Partners — Rob Acton’s firm, focused on nonprofit board placement and governance training

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Jonathan Hicken [00:00:00]: All right, Eric. Here’s what we’re doing today. We are going to draft fantasy sports style draft of our ideal strategic planning teams. This comes from some questions that I often get from people in the community and funders and stuff, which is like, Jonathan, how did you come up with this strategy to be a collaborative center for coastal resilience? Where did that come from? And I’ve actually found that a pretty challenging question to answer because I really did collect a lot of input from a lot of different parties here. And so I thought it might be fun today to actually assemble our ideal teams of influencers when we come up with our strategy.

Eric Ressler [00:00:55]: Okay. Super excited for this. Building a little bit off of the energy of our tier ranking brand strategy video. So we have 10 that we’ve pre-selected, right? We’re assembling our teams. We get to pick one at a time. I guess it’s your episode so you get to go first? How’s this work?

Jonathan Hicken [00:01:15]: Yeah. Couple of ground rules before we get right in. So we’ve listed 10 potential inputs and I’m going to read them randomly so I don’t tip you off into my order here, but here are the 10 real quick. So a trusted consultant, frontline staff, your gut intuition as the ED or CEO, data, the community you serve, your leadership team, major funders and donors, your board, peer organizations, and frontline staff.

Eric Ressler [00:01:45]: I mean, just hearing this list makes me feel for EDs. I have to make these choices and it’s going to, I think, create a little bit more empathy when I get frustrated with clients where I’m like, “Could you just make a choice already?”

Jonathan Hicken [00:02:00]: Yeah, there’s a lot of people we got to listen to. There’s a lot of people.

Eric Ressler [00:02:00]: Okay. I’m excited. Let’s go.

Jonathan Hicken [00:02:00]: So ground rules. First of all, we have to assume for the purposes of this conversation that all of these different parties are trusted people, right?

Eric Ressler [00:02:10]: Good inputs.

Jonathan Hicken [00:02:10]: Good inputs, good relationships, et cetera. So obviously there’s going to be variation in reality. It’s a big leap.

Eric Ressler [00:02:15]: A big leap, but I’ll go with it.

Jonathan Hicken [00:02:15]: That’s going to just be an assumption. And so we’re each going to be creating a team of five. So I will give you the honor of making the first pick. And then I will go and then we’ll go back and forth until we’ve selected all 10. And then if I’ve picked one, you can’t pick it. Off the board.

Eric Ressler [00:02:35]: And then we’re going to have our teams fight at the end or...

Jonathan Hicken [00:02:40]: Come up with the best strategic plan. Yeah.

Eric Ressler [00:02:40]: Okay.

Jonathan Hicken [00:02:45]: All right. So let’s get right into it.

Eric Ressler [00:02:45]: All right. So my first pick is leadership team.

Jonathan Hicken [00:02:50]: Ooh, okay. All right.

Eric Ressler [00:02:50]: Was that yours?

Jonathan Hicken [00:02:50]: It was not. I’m not going to tip that off though.

Eric Ressler [00:02:55]: Okay. So my first pick is leadership team and that is because if I only had one team to assemble to make strategic choices, it would be that team. And I think that’s because if your team can’t be that team...

Jonathan Hicken [00:03:10]: You have the wrong team.

Eric Ressler [00:03:10]: You have the wrong team. And maybe you do have the wrong team and maybe you know that and so that shouldn’t be your first pick. But we’re working off this assumption that all these inputs are kind of where they should be. So in my opinion, at the end of the day, in terms of who actually influences and makes decisions around strategy, it better be your leadership team.

Jonathan Hicken [00:03:25]: So in that, I sort of have some assumptions here, right? That having the right leadership team means they deeply understand your community, they deeply understand the business, they deeply understand operations, funding, budget, et cetera, et cetera, et cetera.

Eric Ressler [00:03:45]: They’ve already probably been influenced by the other nine in their lived experience day in and day out, potentially for years. This gets a little complicated for that reason, but leadership team is my number one.

Jonathan Hicken [00:03:50]: Solid pick right off the top. My first pick is going to be the community you serve.

Eric Ressler [00:03:55]: Ah.

Jonathan Hicken [00:04:00]: Yeah. That was your number two, wasn’t it?

Eric Ressler [00:04:00]: My number two. Yeah. My top three if you hadn’t taken them would have been solid, but okay. I’ll work with it.

Jonathan Hicken [00:04:05]: Yeah. There has to be some signal from the community you serve. If you’re doing a strategic planning thing, that probably means that there’s something needs to change.

Eric Ressler [00:04:15]: Or it’s just three years are up so it’s time for a new strategic plan.

Jonathan Hicken [00:04:20]: Don’t you even start with that.

Eric Ressler [00:04:20]: I’m just saying that’s how they usually happen.

Jonathan Hicken [00:04:20]: Well, that’s too bad because really if you’ve got a great strategy, you keep rolling with it as long as it’s still working and as long as you’re getting results.

Eric Ressler [00:04:30]: I’m half jesting, but honestly, that is often why a new strategic plan happens. But yes, let’s say in the best case, it’s time for a new plan. There’s a pivot that’s needed or the world has changed so you need to rethink the strategy. So yes, continue.

Jonathan Hicken [00:04:40]: Yeah. And look, we exist in this sector to deliver impact to somebody or something. And if we are not deeply in touch with their needs, their wants, their constraints, all of their factors, then why the hell are we doing a strategic plan to begin with? And your point about the leadership team is a good one. First off the board makes sense because hopefully your leadership team is plugged into...

Eric Ressler [00:05:10]: Doing that all the time.

Jonathan Hicken [00:05:10]: Is doing that all the time. Nevertheless, it was my top pick because I want to make sure that whatever change I’m making is going to be delivering better, faster, higher quality impact to that community.

Eric Ressler [00:05:20]: Okay. So you took my number two. Great. I think it’s important to talk about the difference between influence and decision making power. And I think that’s true actually for all of these. But for example, the community you serve, I think absolutely should have a major influence on your strategy, but I wouldn’t put it out to vote. I wouldn’t do a survey that’s like, “Hey community, should we be this type of org or this type of org?” I would do that in the way that we do this work when we are doing data work or survey work or qualitative interviews with the community or the beneficiaries, we are getting those inputs and then we are synthesizing them with other people in mind. We’re not asking those people to vote directly. In my opinion, some of the groups on this list should have more decision-making power. For example, I believe the leadership team should have a lot of decision-making power. The community should have a lot of influence, but I don’t think this work usually works when it’s truly democratic.

Jonathan Hicken [00:06:30]: Yeah. There’s some pitfalls in even soliciting feedback from the community you serve. In my mind, I’m imagining a relatively large group of people, though there may be examples of smaller groups of beneficiaries, in which case the following won’t make much sense, but you got to make sure that you’re asking the right people, that you’re asking the right questions, that you’re going at the right time, that you’re even using the right techniques to get in front of people. There’s a lot buried in that in terms of getting the right input for the process. I agree with you. I’ve seen some pretty far outtakes recently about totally democratizing strategic planning, even down to things like budget spend. I think that’s too far.

Eric Ressler [00:07:15]: I would agree. And if you look at even how our country is built from a governance standpoint and a political standpoint, because it’s going swimmingly well right now, but nonetheless, we have a representative format. We don’t just give individual citizens pure decision making power. And I think there’s a balance there. Sometimes this gets to some of the most difficult parts about doing social impact work, which is like, who should hold the power in this work? And I could see a very valid counterargument to what I’m saying right now saying, “Well, why should EDs get to decide all of this stuff? Shouldn’t it really come down to the community who is benefiting, who’s getting the value out of this work?” And I would say yes to a degree, but also an individual’s vantage point is going to be different, not better, not worse than someone who talks to a hundred of those people all the time. And so all of this requires some level of interpretation and synthesis. I agree that it can get taken too far and I’ve seen this happen with orgs that we’ve worked with before where they’re almost afraid of their community, they’re almost afraid of their staff to the point where they can’t make decisions and just at some point make a choice, which to me feels like a not very effective way of being a leader.

Jonathan Hicken [00:08:35]: Yeah. This is the fundamental problem that you said right at the top, right? There is all of these inputs and all of them are important to some degree and just like having the wherewithal to prioritize them in a way that we’re doing right now, which brings me, you’ve got your next pick.

Eric Ressler [00:08:50]: Yeah. Oh, it’s my turn. Okay. I’m going to do a sort of controversial one. I’m going with my gut intuition Is my next pick.

Jonathan Hicken [00:08:55]: Ooh, okay. So you got leadership team and gut.

Eric Ressler [00:09:00]: So far all I’ve got is my leadership team and gut. I’m hoping to get some other folks on my team here, but I kind of looked at this wrong maybe from a game theory standpoint. I was like, man, if I could get my leadership team, the community in my gut, I’m solid. The rest, I’ll get along on my vision. If I literally only had my leadership team in my gut, hey, I’ll be honest, sometimes I am there in making decisions for Cosmic, right? I wouldn’t probably recommend that if you’re leading the Seymour Center or a community-based organization. I think sometimes gut level decisions get not as much credit as they should, because the body and the brain are actually really tuned to making complicated choices by intuition at a pretty good rate if you have the right inputs in your daily life. If you’re just kind of like the kind of person who’s going to listen to the last person you talk to, your gut’s probably not the right choice. But if you show up in the way that allows you to constantly be pulling and getting these inputs, and then at the end of the day, you kind of just let your brain do its thing almost like shower thought style, I think it’s actually really powerful. Some of my best ideas and my best choices have happened that way.

Jonathan Hicken [00:10:10]: There are levels to these decisions, right? I know that day to day I’m making sort of strategic level decisions from my intuition or with my leadership team and for the purpose of this exercise, we’re kind of thinking of that transformative new strategy here.

Eric Ressler [00:10:30]: Okay. I’m going to say one more thing on this. I think most people actually do use their gut to make these choices anyway.

Jonathan Hicken [00:10:40]: And what? Don’t admit it?

Eric Ressler [00:10:40]: Aren’t even aware of it. And they use these other tools to reinforce the choice they already knew they wanted to make.

Jonathan Hicken [00:10:45]: Sure.

Eric Ressler [00:10:50]: I don’t know. I’m putting the gut up high.

Jonathan Hicken [00:10:50]: All right. My next one off the board is data. Yeah. Look, it almost actually directly counteracts the gut intuition one, right? We have a saying at Seymour Center here where data beats opinions 100% of the time.

Eric Ressler [00:11:10]: Yeah, makes sense for science.

Jonathan Hicken [00:11:10]: Yeah. So I want to make sure that... I mean, you could break this down on all the levels. It could be financial implications, funding implications, staffing implications, community feedback, whatever. I need to have some evidence in quantitative format that where I’m going to head is going to build a stronger business and going to deliver more impact. And I need to see some evidence of that in some ways to almost activate my gut in a way. It’s that affirmation that my gut is real.

Eric Ressler [00:11:45]: That’s right. Well, and it’s what you need to be able to make good gut level decisions. Oddly, you need data to make gut level decisions. So I’m actually really deep in a data focused project for Cosmic right now where I’m building out this internal app and dashboard that gives me visibility into my business. And what’s been fascinating for me is that data is kind of like statistics where you can kind of mold and shape it in certain ways. And so you have to be careful because it’s like, how good is the data? Because sometimes the data is really solid. It’s been done by professional researchers or academics and other times the data is messy or incomplete or misleading. And so it can inform and influence you and steer you in the wrong way too, but you could say, well, the data says. And so all these things have a little bit of nuance, but I had data pretty high up there. I’m sad to see it go on my team.

Jonathan Hicken [00:12:40]: I think that we as EDs and CEOs, we need to learn how to read data because there’s data that’s predictive and sort of empirical and so ironclad that it cannot be scrutinized really.

Eric Ressler [00:13:00]: It’s like self-evident.

Jonathan Hicken [00:13:00]: Right. In other cases, there’s data that’s directional, data that can give you a sense that you’re within the bounds of the decision you want to make. And so when I talk about data, it’s really more that.

Eric Ressler [00:13:15]: Yeah. I think that’s a good way to think about it. That resonates with me when we’re looking at engagement data for websites that we build or for campaigns that we’ve been part of where it’s like you can get so lost in the nuance of like, well, the conversion rate did this one. And it’s like, let’s look at the trends, right? Let’s compare it. Is it up or down month over month? Is it within a healthy threshold or baseline or benchmark that we’re going for? So I agree that directional data is a lot more useful for these big decisions you have to make.

Jonathan Hicken [00:13:45]: All right. Who’s next for you?

Eric Ressler [00:13:45]: Okay. So you took data from me. Although actually data wasn’t next for me, data was a trusted consultant or strategist. Slightly self-serving take. I’ll be the first to admit it. But again, let’s assume trusted is doing a lot of work here. I think having someone who’s not in the weeds all the time to give you that kind of fresh outside perspective is massive because if all you do is talk to your own team and even to a degree, talk to the community that you serve or talk to your board or peer organizations or people who are in this every day, you’re going to get a lot of reinforcement that happens around like, oh, whether it’s because this has been decided, this is the way or this is the intervention. And sometimes you just need someone to come in from a different perspective, an outside perspective who’s like, “Well, we’ve worked with these types of orgs and they do it this way. Have you ever considered doing that?” To just have some new fresh thinking and input. So far my team is my leadership team, my intuition and a trusted consultant, they better be a damn good one. Luckily I still have some picks on the table, but I think that a trusted consultant, trusted, high quality, let’s break down who might some of these people be: strategic planners or XEDs or people from, dare I say the business world, which is like this huge taboo in our space around listening to business advice, which you should be careful about. Design agencies like Cosmic. Who else would you put in this category that you’d be thinking about?

Jonathan Hicken [00:15:20]: Well, I would put you. I’ve had the pleasure of working with you on some strategic level projects and in that case, I think because you are trusted and because you produce quality work, that third party perspective was really influential and sort of in reality the way it played out became super influential in probably ways I didn’t even expect. Now I think where you’re coming from, correct me if I’m wrong, is really the value here of the trusted consultant is that they’re just third party. They’re distant. They have some emotional and just whatever daily distance from what you’re talking about and I think there’s an emotional importance to that. It’s for that same reason that I’m choosing my board off the table next.

Eric Ressler [00:16:10]: Okay.

Jonathan Hicken [00:16:15]: Now there are a lot of caveats I’m about to put on the table about this selection and it goes back to one of our ground rules. We have to assume that these are trusted people.

Eric Ressler [00:16:25]: You’re going to pick one of the 10 effective boards in the... No, I’m just joking.

Jonathan Hicken [00:16:30]: No, but honestly, right? I mean, we don’t have to shit on boards right now and we all know that there is a varying degree of trust in boards and effectiveness in boards. So for me, when I take board off the table, what I’m imagining is a small group of trusted advisors who know your work but aren’t too close to it and bring a variety of perspectives and a variety of talents to the table and serve as that sounding board.

Eric Ressler [00:17:00]: 100%. Real quick for listeners, definitely check out the spotlight interview we did with Rob Acton from Cause Strategy Partners who’s, in my opinion, one of the world leading experts around how to design an effective board for nonprofits. And Cause Strategy Partners was the client of ours, full disclosure, but we learned so much about... I remember in our kickoff, I was like, “Rob, tell me how we can help our clients design effective boards.” And he had really good answers for that and a lot of those are surfaced in the interview. The other thing I want to caveat around the board situation is back to that distinction around influence versus decision making power. Governance boards have a certain amount of decision making power that’s kind of built into the structure, right? We’re working with an org on a rename project right now. The board literally has to vote on that and will make a decision based on that vote.

Jonathan Hicken [00:17:50]: That’s in their bylaws.

Eric Ressler [00:17:50]: That’s in their bylaws, right? But in my opinion, boards should generally be less of deciders and more of supporters to staff. Rob touches on that to a degree and I think a lot of times where boards go wrong is they come in in good faith trying to do their work, but they think the way to do that is to help teach or influence or decide for the staff or they just get really tied to their opinion and think that it should have more influence than it maybe should. And that can happen at the individual level, it can happen at the board chair level, it can happen at the board level more broadly. And then you get into this consensus driven design by committee situation that just waters everything down. So I think board in the best of cases can be a super invaluable asset for all the reasons that you said and especially if they’re there to support and guide, but are also able to detach and let go and trust staff and especially ED to make the final call.

Jonathan Hicken [00:18:50]: So for all of those caveats, that’s why when I take board for my team, it is assuming all of those positive things.

Eric Ressler [00:19:00]: Yes.

Jonathan Hicken [00:19:00]: And I don’t have a board.

Eric Ressler [00:19:00]: Right. Easy for you to stay here.

Jonathan Hicken [00:19:05]: Easy for me to say. Yeah. But you literally are a de facto board member for me. It’s like you are the person I go to to talk about strategy and communications and messaging, et cetera, et cetera, et cetera. I picture you sort of like in this group.

Eric Ressler [00:19:20]: And you’ve got a collection of folks like me who are your unofficial board of directors basically, right? So you’ve got it kind of best of both worlds. You get all the free advice and none of the decision making.

Jonathan Hicken [00:19:30]: Boom. Yeah.

Eric Ressler [00:20:20]: All right. I’m next, right?

Jonathan Hicken [00:20:20]: Yep.

Eric Ressler [00:20:25]: Okay. So I put peer organizations next. So far my team is my leadership team, my gut, a trusted consultant and some peer organizations. I’m starting to feel pretty good, but I do think that peer organizations, again, double edged sword, you have to be aware of the insider think here, but also I’ve learned a lot in my experience talking to other agency owners about like, “Hey, how do you track profitability by project? What’s your formula? Can we just talk shop for a little bit?” And that kind of stuff is so helpful in a way that I’ve had consultants come in and try and tell me to do it a certain way and it’s like, “Well, you’ve never run an agency, right?” That’s an opinion, great. It may be valid, it may not be. So especially if you could, luckily for our listeners, you don’t have to pick only five of these people, but if you could get that kind of peer level perspective of someone who’s been in a similar seat as you and have seen a lot of the same challenges and have maybe overcome some of them who could share their learnings, their failures, that is invaluable. And at the same time, having someone who’s a trusted consultant who maybe hasn’t had that lived experience, but has worked in an adjacent space that can kind of cross-pollinate ideas, all of those inputs are really helpful. But to me, having that peer organization perspective, especially from another leader, especially from one who’s maybe dealt with the challenge that you’re dealing with can be just so helpful.

Jonathan Hicken [00:21:50]: There’s another good reason that they should be on your team and that is they can sometimes be operational partners or collaborators, right? And so deeply understanding the whole ecosystem of work, what role everybody plays, where you fit in, where they fit in, where is the overlap, is your strategy taking advantage of the niche that you might be trying to fit into, right? So all of that input from peer organizations can create this win-win strategy that helps them too.

Eric Ressler [00:22:20]: Helps them too. And like you said, you may go in asking for input on your strategy and you may walk out with that and like a deal to create exponential impact. Okay. So what’s your next pick?

Jonathan Hicken [00:22:30]: All right. Next off the board, just as a refresher, I have the community you serve, data, the board, and next off the board for me is major donors and funders. And there’s the obvious reason, which is like, “Hey, if I do this new strategy, will you fund me?” And that’s obvious, right? Obviously you’re looking for a yes in that. I also think of it as like market research a bit where it’s like, okay, I may have the most beautiful concept for a strategy, but if it’s not exciting, if it’s not solving problems that funders are trying to solve or that they care about, then this idea is dead in the water, right? This is dead before it even gets off the ground.

Eric Ressler [00:23:15]: If you are a social impact organization that relies on a lot of your funding to come from major donors or major funders, they are essentially another major audience of yours, another constituent that you need to serve at some level. We talked about this in a recent episode. There’s a tension there around who should have decision making power and some of the pitfalls of going too far in terms of being donor led in your strategy. But I agree, you could have the best strategy in the world until someone’s not willing to fund it, which honestly to a degree is usually because something’s not penciling out if you’re talking to savvy funders. Not always the case, but I think sometimes there’s a lot of people just kind of like trash talking funders as being out of touch, but good ones are doing a lot of this kind of work, listening to their partners, listening to the communities that are partners serving and they have the ability to synthesize all those inputs so they may see a problem with your strategy that they’ve seen three other orgs try and fail that you aren’t aware of yet, right? A grain of salt with all of that.

Jonathan Hicken [00:24:15]: They play that third party perspective in a way, kind of like going back to the trusted consultant thing, right? It’s like they’ve got that perspective that they may be funding dozens of organizations and they’ve seen this before.

Eric Ressler [00:24:30]: Again, best of faith, these are like progressive trust-based funders. We’re not talking about all the bad funders out there who are just objectively horrible at their jobs. Those exist too. And I would say that in a situation where you came to a funder and you had a new strategy and they gave you feedback that was counter to the direction you were going, a really good one would say, “Hey, let me pair you up with this org that already tried that so you can learn from them. And by the way, I’ll fund an experiment in this direction instead.” So it’s not necessarily a no as much as it is again, like a support and there’s always a tension there too because sometimes they may just call it wrong and your idea was great and they just didn’t see it.

Jonathan Hicken [00:25:05]: I want to call out that my team right now has the community you serve and major funders donors because I think that a good funder is going to ask, what do the people that you’re serving have to say about this? And they should be asking that question. So I got both of those on my team, baby.

Eric Ressler [00:25:25]: That’s a little sad for me.

Jonathan Hicken [00:25:25]: All right, the last two on the board are frontline staff and public feedback.

Eric Ressler [00:25:30]: Okay. So if I’m interpreting public feedback as being not from the community that you serve, just kind of like general public feedback, I am definitely taking my frontline staff. And here’s why I have them kind of low on the list. Some people who maybe are staff might feel a little sad about that. So a couple things. One, if I’m part of the leadership team, I should be listening to these people all the time. So rather than bringing them in only for a strategic planning session, and also sometimes the staff actually doesn’t want to be part of these decisions, which I think is something that people don’t think or talk a lot about. There’s this movement to like be flat and democratic and everyone... And look, I’ve tried that a lot of times and we do that for certain things, but I’ve also learned sometimes that’s actually a burden you’re placing on someone who’s like, “I didn’t sign up for this, man.” If I wanted to be the executive director, I’d be working towards that right now.

Jonathan Hicken [00:26:20]: Isn’t that your job, bro?

Eric Ressler [00:26:25]: Isn’t that your job? Why are you making me decide these things? This is above my pay grade and also maybe you’re not actually paying me enough to even be carrying the stress of a decision this big where maybe even lives are on the line. So again, you have to kind of consider all of the context around this, but I do think the staff can have some good input absolutely and it just needs to be interpreted correctly because there are also cases where staff have really strong opinions and the loudest voice is not always the most accurate one. And sometimes I’ve seen EDs feel like, again, even afraid of what their staff is going to think about these choices. To me, that’s a symptom of a deeper problem beyond just like you might be slightly off on your strategy.

Jonathan Hicken [00:27:05]: At the Seymour Center, the frontline staff are interacting with our visitors that are coming in the door. And so for me, when I went through this exercise of ranking, I chose the community I serve first and when I go to my frontline staff for feedback on stuff, it’s to channel the voice of the visitor, right?

Eric Ressler [00:27:20]: You kind of cut in line.

Jonathan Hicken [00:27:25]: Exactly. Went right to the source. What are you hearing on X? And we can get that quick feedback. So it’s not that I don’t value the frontline staff feedback, it’s that what I’m asking them for more often than not is what are you hearing from visitors? And I already took them off the board.

Eric Ressler [00:27:40]: Okay. So let’s go through our teams then. So I’ve got my leadership team, I’ve got my gut, I’ve got a trusted consultant who’s going to be a really good one, hopefully. I’ve got input from peer organizations and EDs and I’ve got my frontline staff. I feel pretty good about my team.

Jonathan Hicken [00:27:55]: So that’s a pretty damn good team right there, dude. All right. So I’ve got the community you serve, my data, my board, my funders and public feedback, which we didn’t really define or talk about real quick. That was basically like online, right? I think of social media immediately of like, what do people online have to say about my brand or my work or whatever?

Eric Ressler [00:28:15]: Yeah. Okay. So like the Instagram comment section, the Reddit threads, the op-ed comments that come in.

Jonathan Hicken [00:28:20]: That’s it. Yeah.

Eric Ressler [00:28:25]: Let’s put that down way low.

Jonathan Hicken [00:28:25]: Yeah, I know. So I feel like they’re kind of dragging my team down a little bit more.

Eric Ressler [00:28:30]: Well, you got the community, so it’s only fair.

Jonathan Hicken [00:28:30]: Yeah. And I mean, both of our teams at the end of the day, if we put your team up against my team and said, who’s going to come up with the best strategy for X, Y, Z organization, I think there’s an argument that both are positioned well.

Eric Ressler [00:28:45]: I think so too. And let’s take this back to our listeners who now are like, “Okay, well, I don’t have to only pick five people from my team, but I do need to figure out who do I listen to when I’m going to make big strategic choices? How much space or influence should I give them?” So I’d be curious to hear, how do you think about that when you’re making choices as an ED?

Jonathan Hicken [00:29:05]: Well, you alluded to this earlier around the inputs that inform you. There’s also the relationships that influence your thinking and of course then there’s the deciding part. And really at the end of the day, I feel like my job is so much about synthesis. It’s so much about understanding what’s happening around me and it’s about developing really trusting relationships that I can go and sort of make sense of the noise and that’s really truly the sequence that it goes in, right? It’s like, here’s what I’m seeing, here’s what I’m thinking, here’s what I’m hearing, what do you think about that? So it really does factor in all of these inputs, but there’s an element of, and part of it is just getting the reps in of knowing when a signal is a fit or not.

Eric Ressler [00:30:00]: Dare I say that you use your gut to make those choices. Isn’t it kind of that?

Jonathan Hicken [00:30:05]: Yeah, I mean honestly though, right? But also it’s the loudest voice in the room thing. You start to sort of pick up like, okay, hey, this is loud. And I want to understand if there’s an important reason behind the loud, but I’m not going to just overweight the loud because it’s loud.

Eric Ressler [00:30:25]: I think the other thing to acknowledge here is that sometimes there is just some politics, especially when it comes to the board or a major funder where it’s like you got to throw them a bone or you might know this is the right choice, but you have to just do a cost benefit of like, is it worth fighting this battle at this moment? And for big strategic decisions, I would argue it is. But for other things, pick your battles. And ultimately that’s maybe not the exact right language to use, but I would say that this is complicated work and I do think the way that we do this when we help guide strategy for clients is we do have an early inputs phase. Even when we’re bringing a new client on, there is no bad document for you to send me. I want everything. I want to see what are the raw ingredients we have to work with here. I want the data. I want to know if it’s good data. I want to know if it’s bad data. We do interviews. I want to do sessions with the board. I want to do sessions with the community. I’m going to do my own audits. I want to just get everything. But then you do have to start to look for patterns, look for trends, look for energy that’s like moving in a particular direction. And then towards the end, as you’re coming down to making a choice at some level, you do have to just make a choice as a leader. You have to take all of those things and know that you’re never going to make perfect choices, but you do need to take action. And that’s the thing that I would recommend and that I get frustrated about the space sometimes is like sometimes I feel like we’re actually really good at doing these input exercises and sometimes they’re authentic, sometimes they’re more performative, but we feel really good about that as a sector. But how much data do we really need before it’s just like back to one of our old concepts, MVS, minimum viable strategy. You could plan forever, but the only plan that really matters is the one that you actually execute on. And when you start to execute on it, then you learn, then you iterate, then you keep going. So hopefully that helps listeners who are like, “That’s a lot of inputs. What do I do with all of this?” I would say have discreet phases and containers for these things and be really clear with the people who you’re asking for their time and energy. “Here’s what I’d like from you and here’s how we’re going to use that.” Because I think a lot of times what happens here is people think they have more power to influence decisions than they actually do or than you want them to and then they feel disappointed or angry or insulted when their vote didn’t really count the way they thought it would.

Jonathan Hicken [00:32:50]: I think the power of finding a win-win is sort of underrated, frankly. When I get inputs from all of these sources, the way my brain is tuned is I’m constantly looking for that win-win, a decision or a direction or an action that’s going to accomplish multiple stakeholders’ goals at the same time. And that’s A, to deliver more impact more quickly, more effectively, but also it is a way to get a quicker yes. Where if I’m coming to the table with a partner or a funder or whatever and I can clearly articulate why this thing is good for you, that’s a quicker way to a yes.

Eric Ressler [00:33:30]: I think that’s true. I think the near enemy of that is the trying to please everyone. I kind of have an internal gauge for these types of decisions that if literally everyone is happy, maybe the decision was too obvious and weak and there should have been a little bit more of a bold choice made.

Jonathan Hicken [00:33:45]: Yeah, fair enough.

Eric Ressler [00:33:45]: I don’t think that’s what you’re saying. I just, for listeners, because I think honestly, what people often do is they do try to come to this situation where the board’s happy, the staff is happy, the community’s happy, everyone feels good. And usually that means you didn’t take a big enough swing.

Jonathan Hicken [00:34:00]: Yeah. Let me be a little more nuanced in my position on that because the outcome I’m looking for when I look for that win-win is not the happiness scale. What I’m looking for is results, like business results or organizational results or whatever where it’s like the funder and the partner, whatever decision I’m about to make is going to help them be successful as defined by their own organization’s goals.

Eric Ressler [00:34:25]: So they might even disagree with the way.

Jonathan Hicken [00:34:30]: Exactly.

Eric Ressler [00:34:30]: But at the end, they can’t argue with the...

Jonathan Hicken [00:34:30]: With the results, exactly. So it’s not about finding emotional harmony. It’s a cheat code almost that’s going to unlock everybody’s success. So anyway, for what it’s worth.

Eric Ressler [00:34:45]: I like that thinking and I like the idea of just honestly being pragmatic around people are going to be influenced by things that benefit them. And so I mean, that’s true for the community you serve. It’s true for your funders. We talked about this in a previous episode where it’s like understand your funder priorities and understand hopefully they’re transparent about those things and they’re consistent with them, which neither of those things are always true. But when you can get that, then you can figure out where is their authentic overlap and our mission and the things they care about funding, then you’re off to the races.

Jonathan Hicken [00:35:15]: Yeah. So going back to how I started the episode of like, how do I answer this question? Really what I answer is, “Hey, I got a lot of feedback from a lot of people and I tried to find the strategy that was going to fit with all of those inputs.”

Eric Ressler [00:35:30]: At the end of the day, what else can we do? This one was fun. We got to find more ways to do these tiering things.

Jonathan Hicken [00:35:35]: Yeah. We’d love to hear the listeners feedback on this too. You built a hell of a team, Eric, for your strategy input.

Eric Ressler [00:35:40]: Likewise.

Jonathan Hicken [00:35:40]: All right. Thanks so much.

Eric Ressler [00:35:40]: That was fun. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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Most people who’ve heard of a community foundation think of it as a place to park charitable dollars. Kristin Todd would tell you that’s the least interesting thing it does.

Kristin is President and CEO of the NoCo Foundation, the community foundation serving Northern Colorado. She came to the role after years as executive vice president for the Daniels Fund, one of the largest private foundations in the Rocky Mountain West.

That path, from a national legacy fund to a place-based one, shapes how she sees the work: a community foundation isn’t just a philanthropic bank, it’s one of the few players that can get donors, nonprofits, and the wider community around the same table and actually move something forward.

Housing is the example she keeps coming back to. In a two-county region split between conservative ag country and a progressive university town, she’s the one who can pull mayors, developers, city planners, and nonprofits into the same room, because the foundation has no axe to grind and 50 years of trust to draw on. She calls it being Switzerland. It’s also a good description of the whole job.

She’s a pragmatist at heart. She’d rather get people in a room and move than run another study to be sure. Compromise, act, learn in the real world instead of the boardroom. And after thirty years in this work, what keeps her going isn’t that the sector’s had an easy run lately, it hasn’t, but what she watches people do when their community is on the line.

She and Eric get into why she’d rather call nonprofits businesses than charities, what a community foundation can do that a billion-dollar legacy fund can’t, and why local work beats national fights.

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Episode Highlights:

[00:01:00] Running a $1.5 billion legacy fund vs. a nimble community foundation
[00:04:30] The three buckets: the philanthropic bank, strengthening the sector, and the wicked community problems
[00:07:00] What nonprofits are actually facing right now, and why mergers stopped being a taboo word
[00:08:00] “What if the disruption is the new normal?”
[00:10:00] Fewer donors, bigger checks, and the rise of the donor-advised fund
[00:11:30] How NoCo doubled its grant-making by keeping money in motion
[00:12:30] The 5% floor that became a ceiling
[00:19:00] The narrative problem: “And you do all of that as a volunteer?”
[00:20:30] Stop calling them charities. They’re businesses with social impact.
[00:28:30] Becoming the Switzerland of a divided region to solve housing
[00:34:00] Punching above your weight locally instead of waiting on Washington
[00:36:00] What keeps an eternal optimist going

Notable Quotes:

[00:12:30]: “In the private foundation world, that 5% has become a ceiling, not a floor. It was intended to be a floor and it is a ceiling.” Kristin Todd

[00:11:30]: “We do not want to be a sponsor of DAFs that are warehousing dollars, and in fact we are not.” Kristin Todd

[00:08:10]: “What if this time of disruption is the new normal, and it’s not going to settle down?” Kristin Todd

[00:21:30]: “These are the hardest problems in the world that no one else has solved, and yet they’re not getting the same attention as the latest AI startup.” Eric Ressler

[00:13:10]: “It’s almost like a reverse anchor. You now have permission to only spend down that much.” Eric Ressler

[00:31:20]: “We can be Switzerland. We can get mayors and city planners and real estate developers and nonprofits all at the same table and say, we’ve got to work together.” Kristin Todd

Resources & Links:

• NoCo Foundation — the Community Foundation of Northern Colorado, where Kristin serves as President & CEO

• Daniels Fund — the private foundation where Kristin previously served as Executive Vice President

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Eric Ressler [00:30:00]: I’m picking up on some just logical pragmatism that’s refreshing to hear because I think sometimes in this space every decision gets analyzed and picked apart. And at some point we just have to do our best here and then learn in the real world instead of in the boardroom. Kristin Todd, welcome to the show.

Kristin Todd [00:00:55]: Thanks so much, Eric. It’s a pleasure to be here.

Eric Ressler [00:00:55]: So I think where I’d like to start today is just to hear your perspective as you’ve transitioned from a much larger foundation where you are overseeing upwards of $50 million in annual giving to a community foundation where maybe the sheer amount of giving is a little bit less, but the impact hits in sort of a different way. So I’d love to just kick us off by understanding from your point of view, what is the difference in running a fund of those different sizes and those different trajectories?

Kristin Todd [00:01:25]: Yeah, I love that question because it’s been a journey for me and I have lots of thoughts on that. I came from working for two different private foundations where you’re working for the legacy of one single individual or one single family. In my case, neither of those parties were still living. And so I was part of a staff executing on someone’s vision. And while the resources were vast, I often felt like there was some level of disconnect between what the community needs here and now versus what someone’s thought and approach and legacy might have been decades before. And so being on the community foundation side where you are truly place-based and you are truly working in the moment, helping a community solve some of its biggest challenges, in my opinion, allows us to go deeper, be in partnership with the community and figure out the best way to invest those dollars in a way that is focused on the here and now, on what the issues are, in a way that you’re not able to do when you are executing someone’s vision that may have been identified many years earlier. And it’s not that that legacy is a bad thing. It’s just not as nimble as I believe we can be in the community foundation space where we can shift on a dime as the community needs are changing.

Eric Ressler [00:03:05]: You surfaced really early on an interesting tension from my point of view, and this starts to really bubble up to the contradiction of philanthropy in general, which is that for a lot of institutional philanthropy, wealth was gained through often private markets and the priorities are often shaped by whoever was in charge of that wealth and their priorities and what they care about in the world. And in the best of cases, they care about things in the world that are real problems that need to be solved and it all works out. And nonetheless, who gets to decide which problems are most important in the world? The pro-government crowd would say, well, that’s the purpose of government and your representatives and who you vote for. So it’s a tangled mess, this whole space. And so what I love about the frame of a community foundation, as you mentioned, is that it’s place-based, it’s nimble.

Kristin Todd [00:04:30]: Yep, you bet. So I answer that question with a little bit of a framework of how we organize our work, because to me it’s at the crux of what we do and how we try to be matchmakers between community need and donors. And so at the NoCo Foundation, and I don’t think this is dissimilar from other community foundations, maybe my bucket analogy will be different. People use different language, but I use three buckets to describe our work. One is sort of bread and butter community foundation work where we are aggregating dollars, we’re a philanthropic bank, if you will, we’re the philanthropic easy button. We’re helping donors and DAFs give responsibly. I think every community foundation does that. Our second bucket is working to strengthen the nonprofit sector. Our belief is that if we have a healthy, robust, vibrant nonprofit sector, philanthropic dollars go further, quality of life is enhanced, community wellbeing is enhanced. So what can we do from our position as a community foundation to work to strengthen the capacity and the health of our nonprofit sector? And then our third bucket is, what are the greatest needs in the community? How do we know that? So we are producing reports, we’re doing community indicator reports. We understand what the greatest needs are and we are bringing people together to solve big wicked societal issues. In our case, we’re working on water sustainability. We live in a high desert area in Northern Colorado. Water is a big issue. Affordable housing is arguably our largest complex challenge. So what are those issues that we as a region are facing and what’s our responsibility and our ability to convene and catalyze and move the community towards solution? So that framework is our three buckets of work. To answer your question, it’s how do we create continuity and crossover among those three buckets? So how do we educate our donors who are making grants out of their donor advised funds? How do we educate them on our bucket three work, which is what are the greatest community needs, making sure or at least encouraging them to give dollars toward those greatest needs, and better yet, are they willing to come alongside us in the work that we’re doing on affordable housing, water sustainability, and help support that work? Likewise, if we can play matchmaker between the nonprofits in bucket two with those donors, we again are doing the best service to the greater good and the community. And so how do we blend those three buckets is how I think we sit in a position to get at what you’re talking about.

Eric Ressler [00:07:20]: I want to focus for a minute on bucket two, strengthening the nonprofit community. It’s been a tough couple of years just at large for nonprofits in America especially, but I would say the social impact sector has been tumultuous with the funding ecosystem in rapid change right now. What are you seeing on the ground as surfacing as some of the greatest needs and some of the greatest challenges that nonprofits are facing right now?

Kristin Todd [00:07:45]: Yeah, I agree. It is certainly a time of chaos and disruption and a lot of nonprofits are feeling that, they’re feeling it daily. And from where we sit at the community foundation, I think we’re able to be a trusted resource and a trusted advisor to our nonprofit community. And some of the things that we’re seeing are, my observation would be, what if this time of disruption, we’re not waiting for the new normal to happen? What if this time of disruption is the new normal and it’s not going to settle down? And so how do we equip our nonprofit leaders to be resilient and to be bold and to be strategic and to figure out how to navigate if this disruption is the new normal? And I would borrow Churchill’s words to say, never let a good crisis go wasted. So what can this crisis teach us about being resilient and maybe being creative and doing things differently to allow us to come out stronger? Dare I say on the other side, because there may not be another side. It may be this may be the new normal. And so we’re brokering a lot of conversations right now about strategic alliances, mergers even, and taboo words in the nonprofit sector that have been very difficult in prior years are becoming more and more a reality. And thankfully, I feel honored that the community foundation is this trusted resource where nonprofits in our community are reaching out to us and saying, will you help us? Would you bring some of our stakeholders together and help have this conversation? And so we’re seeing things along that whole spectrum of people, organizations really looking at full mergers to the other end where maybe it’s just a strategic alliance or some kind of shared service model that will help them really get through these trying times.

Eric Ressler [00:10:05]: One of the things that we’ve heard over and over again on our show and just observing the space is that there actually is more money than ever before being poured into nonprofits, especially from private individuals. But the concentration of that money means that there’s less donors overall, but the donors who are giving overall are giving more. And I think what that’s leading to alongside the disruption in government funding is more and more nonprofits essentially competing for these resources and shifting their modalities of fundraising more towards high net worth individuals, donor advised funds, which have been this kind of standard thing for community foundations since the beginning, are now becoming this hot vehicle for giving in a way that I think is different than even a couple years ago, at least from my view. And there’s some criticism about DAFs too, right? DAFs are a great way to park your wealth and there’s not requirements around how much you spend down. And then the pro-DAF people will say, well, actually on average, DAFs spend down faster than private foundations. So how do you ensure as the broker of impact between boots on the ground social impact organizations and generous donors in the community who want to give back that those dollars are being spent not just wisely, but they’re actually spending down in this time of need?

Kristin Todd [00:11:25]: It’s a good question. And from where I sit in our community, we talk about money in motion. And so we do not want to be a sponsor of DAFs that are warehousing dollars and in fact we are not. And so in the five years that I’ve been here, we’ve been able to more than double the grant making that we are putting out through our DAFs into the community. And I would argue that that is largely because we are being more proactive in working with our donors, introducing them to nonprofits, getting nonprofits in front of our donors and playing matchmaker. And so we are very intentionally doing everything in our power to make those dollars move. And it’s been very successful here in our community. We went from granting $7 million annually pretty steadily and now we’re at about 16 and a half million annually and we continue to grow, and it’s simply because we are intentionally saying, here’s a need, here’s a project, and putting people together. And I would say in the private foundation world, that 5% has become a ceiling, not a floor. It was intended to be a floor and it is a ceiling. And in our community foundation, and I believe nationally, DAFs are putting out upwards of 15, 18% a year. And so I think if we put a percentage requirement for DAFs, we might end up in the same place where that becomes a ceiling and not a floor. I don’t know. That’s kind of been my experience coming from private foundation to community foundation and seeing the difference between the two.

Eric Ressler [00:13:10]: It’s almost like a reverse anchor. It’s like you have now permission to only spend down that much. Whereas now because there’s no minimum, it actually doesn’t anchor the DAFs to be there. I’ve never actually thought about it that way before, but it’s intriguing. I do wonder, one of the things that we hear even major private philanthropies say is like, well, we need to make sure that we are making investments so that our endowment and our funds can grow so that we’ll be here in 10 years when we’re still needed. And I think there’s some good truth to that to a degree, but I also think that we’re coming out of a time where those funds are gaining much more than 5% per year over the last five years on average. And we’ve seen even some admirable commitments to six, seven, 8%, sometimes even more. We’ve interviewed folks on the show who have become a spend down philanthropy where they’re spending their money down as fast as they possibly can. I’m not here to judge one way or another. I have my own beliefs on this, but I’d be curious to hear from your view how you think about that spending down, accelerating, getting money into the community and also ensuring that there is coffers for the next need that happen the year after and the year after that. How do you think about that balance?

Kristin Todd [00:14:25]: I guess I would say I don’t think there’s one single answer to that. It’s complicated and I think probably a balanced approach is what will serve us best. I do believe that there is an argument to be made for endowing funds for the future and to maintain those sources of funding for future generations. And also I recognize that the needs are great today and we shouldn’t not spend today. And so I do believe that there are so many different types of philanthropists. There are different values, there are different approaches that my hope is that the tent is big enough to bring all philanthropists together and embrace whatever feels right to them. And then in the aggregate, we’ve got some that are spending down, we’ve got some that favor spending today and some that favor spending in the long term, but on the whole, we’ve got a balanced approach.

Eric Ressler [00:15:30]: Hey friends, real quick before we continue today’s episode, I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative, and digital experiences. Our work together helps you earn trust, connect deeply with your supporters and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com.

All right, back to today’s conversation. From the point of view of a community foundation, you have a unique setup compared to some private foundations where the initial investment is there and the only way for it to grow is through future investments of that initial capital. Whereas from a community foundation standpoint, there’s constantly new sources of capital being invested year after year. So in the best case scenario, every year more and more money is coming in and more and more money is going out.

Kristin Todd [00:16:45]: Yeah, 100%. And I think again, that speaks to the versatility and the nimbleness of a community foundation, that we can meet the moment and we can meet donors and philanthropists’ desires today and we can also meet donors and philanthropists’ desire for building a legacy for the future. And as long as we’re doing both and filling both coffers, I feel like it’s the best of both worlds. At the end of the day, we consider one of our core values and at the core of our mission is to inspire more philanthropy and to bring in all kinds of philanthropy and meet people where they are and help them think through what’s important to them and why, and how do you factor in the needs of the community so that community needs are also part of the mix. But the more philanthropy we can bring to bear, the better off we all are. And so we do a lot of listening for new donors and new folks that are coming into our world to say, what do you want to accomplish? What is meaningful to you and how do we help build a vehicle and a plan that achieves that?

Eric Ressler [00:18:00]: One of the things that I’m particularly interested in as we work with our clients and just as a curious person about this space and how social change happens is, how do we build a more resilient social impact and nonprofit sector? And I think that’s a really big question that we’re certainly not going to answer in our show here today, but I like to poke and prod at it and get my guests’ thoughts on those things. And one of the things that I think clearly isn’t working is when nonprofits are under-resourced for the scope and the scale of the missions that they’re set out to create. And so we’ve seen a lot more sector-wide pontificating about trust-based philanthropy and multi-year general operating support and trying to get away from measurement of success being measured only by overhead percentage. So I see those conversations happening in my professional life and then in my personal life, talking to friends, talking to family, it feels like those conversations are just not breaking through to the public. And if anything, there almost seems to be more skepticism of nonprofits and social impact organizations being scams or tax write-offs. What are you seeing out there in this space? Is this just internet talk happening?

Kristin Todd [00:19:15]: I am an eternal optimist and I have spent my entire career, so now more than 30 years in the nonprofit sector, in the social impact sector. I picked up that you’re calling it social impact sector and I think that’s part of the issue, right? I think we’ve got a narrative problem and I think that people hear about, oh, these cute little nonprofits, these cute little charities, that they’re not doing real work. And I think about this story, a dear friend of mine who’s been a nonprofit CEO of a major, major social impact organization and was on a flight sitting next to someone, had a two hour conversation talking about all of the great work that they do, the significant deep work that they do, and the woman who herself was an executive said, and you do all of that as a volunteer?

Eric Ressler [00:20:10]: Right.

Kristin Todd [00:20:15]: There’s just this complete disconnect and lack of understanding. I think part of it is our own nomenclature of calling it the nonprofit sector and the charitable sector, which somehow to me feels less than. How do we change the narrative to say these are businesses, they are businesses that have social impact, and how do we educate the general public about the importance of these organizations to our society, civil society?

Eric Ressler [00:20:45]: 100%. I mean, preach it. I so agree with you. And that’s one of the reasons that I’ve deliberately always used social impact to describe this sector, A, because it’s not just nonprofits, right? It is public-private partnerships, governments in the mix, funders are in the mix, some of which are nonprofits, some of which are not. And I believe that’s what it’s going to take. And I do think there is this kind of like, oh, isn’t that cute, you’re doing good work and you’re passionate about it, but we know this isn’t as serious as working for a tech company for some reason. But when you’re in this space and if you’ve been in the seat as an executive director or a funder or even like my point of view, supporting and being inspired by these organizations, you realize these are the hardest problems in the world that no one else has solved or is willing or able to solve, and yet they are not getting the same amount of time, energy, resources or attention as the latest AI startup. And so there is this contradiction and I don’t know if this is because we’re so motivated by profit here in America and globally to a degree as well, or because there are some examples of organizations that can’t break past that like, well, it’s a good cause but the impact frankly isn’t really meaningful. And that does happen too, because going from zero to one as a social impact organization is really difficult, and when it’s being funded by generosity, there’s this extra scrutiny that’s attached to it. Whereas if a billionaire investor loses all of their investment on a new tech startup, no one’s shedding any tears over that, which I think is right overall.

Kristin Todd [00:22:25]: There’s this total double standard and lack of understanding that we should not fund capacity and infrastructure of a social impact organization and startup and capital and investment in the same way that we do in the private sector. I don’t know what that is, but I hear you and it is a complete disconnect. And until we can really, I think, genuinely treat the social impact sector as essential and not this nice to have and invest in the infrastructure of those organizations in the same way, we’re not going to get there. But I, again, I’m an eternal optimist and I feel like there’s a little bit of a shift happening. And to bring it back to this disruptive time we’re in right now, what opportunity, I guess, is what I would ask is how can we use this time of disruption to further that cause that it sounds like you and I are both a part of?

Eric Ressler [00:23:30]: Yeah. And I feel like we’re up here in the clouds and I can hang out here all day, trust me, but how do we bring this back to, if there is a nonprofit executive listening to the show right now, they’re well aware of the pain of this problem, and maybe they haven’t thought about it in exactly this way, but most likely they have, and yet they’ve got payroll to make next week, right? They’ve got a program that just got spun down because what used to be a government grant just disappeared overnight last year. So what do we do about it? What are the practical things that, and I have my point of view on this and it comes really from communications and brand building and identity and the things that I specialize in that I do believe are a huge lever that’s underutilized for all the reasons we were just talking about.

Kristin Todd [00:24:25]: I would say like any nonprofit exec that is listening, if you’re not already connected in a peer network, that’s a place to start. And to reach out to your local community foundation, or if there is a private foundation that you have a relationship with, see if they can partner with you to be a convener or an intermediary, for instance. So we do several things here in Northern Colorado. We have created a peer network of nonprofit execs. They get together monthly, and on one hand they are each other’s support system and they can share challenges and good news and highlights, and we can listen and mine for common challenges that are surfacing in the group, and then we have gone and created programming to bring back to them. And so we’ve created a training, or we contract and bring experts in on branding, communication strategy, advocacy, board relations. And so we can bring resources to the sector, to this peer network. And the luxury we have is that we’re not leaving those peer network meetings and going back to be in our jobs where you’re worried about making payroll and you’re worried about running the nonprofit and all of the things. We can continue to look at it from the 30,000 foot level and hear what the needs are and bring resources and continue to convene and create partnership and peer networks. That is at least a start. So nonprofit execs know that they’re not in this alone and there is power in numbers, and there are these intermediary organizations like a community foundation that can serve that role.

Eric Ressler [00:26:20]: Yeah. And I think that from my point of view, before I was in this space, I had maybe tangentially heard of the community foundation here in Santa Cruz where I am, but I didn’t really know exactly what they did. And I actually didn’t realize similarly how much a community foundation is an important element of gluing the community together, especially in times of true disasters. So environmental disasters, like a community foundation is one of the first places to activate support networks, money, funds, whatever it takes. Do you think there’s a similar thing that happens for nonprofits as well where they’re just not aware of the benefits of being in network with the community foundation?

Kristin Todd [00:27:05]: I think for sure. And again, I think that there’s 900 community foundations around the country. We often laugh and say, you’ve met one community foundation, you’ve met one community foundation. So we’re all different, but it’s certainly a place to start. And more and more I’m seeing community foundations lean into their role of exactly what we’ve been talking about. Getting outside of just being that philanthropic bank, getting outside of just servicing the donors and the donor advised funds, and really leaning into community and leaning into the health and wellbeing of the nonprofit sector. So I think it’s a great place to start as a nonprofit social impact ED. If you’re not connected with your local community foundation, it’s a great place to reach out and figure out if there is something happening there that you could be a part of.

Eric Ressler [00:28:00]: Let’s talk a little bit about, you mentioned at the top of this episode, one of the things that you’re doing is listening and unearthing what the greatest needs of a community are. That sounds like difficult work to me when there’s so many competing priorities, when things are becoming polarized and divisive. Let’s even just take the example of housing. Huge issue here in California, even very directly here in Santa Cruz where I am, but becoming more and more of an issue across the United States, and I know it’s an issue in Colorado as well. How do you as an organization figure out how to assess the need, how to prioritize and stack rank the needs? That’s messy work. What’s your process like there?

Kristin Todd [00:28:40]: So it is messy work and I would say it’s evolving and I’m not sure that we’ve got it all figured out, but what we have done is we often start with data. And so I live in a region, Northern Colorado, and it is primarily a two county region that we serve and the two counties are very different. One is like ag, oil, very much more conservative. The other county is much more progressive university town, et cetera. So very different politically, geographically, industry across the board. Yet the issues don’t change when you go across the border. Housing is still the number one issue. And so we started with data, and there had never been a two county regional community needs assessment or a community indicator report that had ever been done. So we thought, well, that’s a value add that the community foundation could do. And I would also add that we are this trusted institution. We’ve been around 50 years. We’re very careful to say neutral in the sense that we can bring lots of different perspectives to the table, not neutral in that we don’t have an opinion, but people will come to the table when we invite them. So first we start with data, and right now housing is one that no one can argue with right now. It is our number one issue and we are on this trajectory that is just untenable for our region. And so the data bears that out. And so then we are able to say, okay, let’s start working on this together. Let’s get out of our silos. Let’s get our municipal leaders to the table. Let’s get our developers to the table. And two sides that don’t always see eye to eye. And so the developers often point fingers at the city planners and vice versa, and you’ve got the narrative of the greedy developers. Well, really none and all of that is true at the same time, but if we don’t come together at the same table and try to figure it out, we won’t get anywhere. And so I think because it’s an acute issue and people know that and they’re willing to say, okay, everything’s got to be on the table because we can’t continue in the way we’re continuing. And then if we invite them, they will come. And we have had really rich conversations over the last year with all facets and all perspectives of the issue, and we’re starting to get somewhere. But I think it’s this unique role that a community foundation can play and does play in many, many communities around the country, that we can be Switzerland. We don’t have geographic borders and we can get mayors and city planners and real estate developers and nonprofits all at the same table and say, we’ve got to work together.

Eric Ressler [00:31:35]: Yeah. I’m picking up on some just logical pragmatism that’s refreshing to hear because I think sometimes in this space, and I think it’s exacerbated by this media environment that we’re in where every decision gets analyzed and picked apart and agendaized if that’s a word. And at some point we just have to do our best here. We have to take the inputs and we want to be diligent and we want to be rigorous around how we do that, but we’ve seen that diligence and rigor progress to a fault where we could spend years running studies and reports and doing listening sessions and community convenings. And at a certain point some stakeholders just need to make a call and do what they think is best and execute and then learn in the real world instead of in the boardroom. And I think that striking that balance is a really tough position to be in as a leader, especially when positions that used to be kind of insulated from too much public opinion, maybe you’d get a bad op-ed, now suddenly people can show up outside your house and stalk you on social media. And so the stakes are a lot harder. And what I worry about is we’re seeing, or I’m observing, less people being willing to engage in quote unquote politics or even just civic engagement in general for fear of just being ostracized or just the exposure of being a public figure at all. And I think that’s a bad trajectory.

Kristin Todd [00:33:00]: Yeah. I mean, what I see here, and knock on wood, is those two counties that I described could not be more different, but there’s a level of pragmatism where, and I don’t know that this is everywhere, but here in Northern Colorado, leaders are willing to come together and put differences aside for the good of the community and will find that there is often more common ground than they would think. And so it just sometimes takes somebody to get everybody together and go through an exercise and talk about values and what do we want for our community and what do we want our community to be for our kids and our grandkids? And then we see that we’re really pretty well aligned on that visioning. And so then we just have to figure out what are we going to compromise on and what are we going to do to move this forward? But there is a level of pragmatism that I feel like is baked into at least this region, which is helpful.

Eric Ressler [00:34:00]: Yeah. And to almost argue with my last question to myself, how much of that is just the internet and let’s go touch grass. And when I’m in these rooms where sure, there’s divisive meetings and there’s organizing and some of that’s just like healthy politics, right? We should have strong opinions on these things, but at the end of the day, I think we need to just be in action, right? That is the main thing, because if we don’t move, we’ll never fix these issues. And we have to be willing to move and fail sometimes.

Kristin Todd [00:34:30]: Yes. My experience in working at the local level is there is far less divisive vitriol than there is at the national level. And I think if we can just focus on our local communities, we’d be so much better off.

Eric Ressler [00:34:50]: I think that’s really good advice in general and something I’ve been thinking about a lot and feeling the urge to get more involved in not even just like local politics, but just like local community in general and civic service and the issues that I care about and supporting some of the nonprofits that are doing good work around education or advocacy or infrastructure or whatever the things are. Transportation has been on my mind a lot as something that, coming back from a trip in Europe and coming back to America and saying, being reminded we’ve got a lot of work to do on transportation even in our own community here, and feeling the urge to be part of that. So I think that’s a really good thing to consider, like what is your sphere of influence? And you can usually punch above your weight locally compared to national issues. National issues matter. We can’t solve everything at a local level, but there’s a lot that we can solve there.

Kristin Todd [00:35:40]: I think that’s true, totally. We can’t put blinders on and pretend like the national dialogue is not happening and there’s not that context, but I’m filled with gratitude and optimism every day seeing what is happening at the local level.

Eric Ressler [00:36:00]: So as we move to wrap up, I’d actually like to end there. You describe yourself as an eternal optimist. I love asking this question to our guests on the show. What is it that keeps you in that space and keeps you going even when it does get tough, either personally or in the moment in your community? What keeps you in that eternal optimist mindset?

Kristin Todd [00:36:15]: I think seeing how deeply people care about their community and how they are willing to show up and give back and solve problems and do hard things. People really care about their community, and when something is at risk for the future of their community, people show up. And so I see that every day and it gives me hope and fills me with optimism. But seeing how people show up is really what gives me that sense.

Eric Ressler [00:36:50]: Amazing. Kristin, I think that’s a beautiful place to end. Thank you so much today for your time and sharing your point of view on this work. It was really inspiring and hopefully have you on the show again at some point in the future.

Kristin Todd [00:37:05]: Sounds great. Thanks so much for the opportunity.

Eric Ressler [00:37:10]: If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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There is a comfortable story going around right now. Social ate the web. Then AI ate search. So the website barely matters anymore. I don’t buy it.

Your website is the one channel you actually own. It is the one place you control the narrative and the experience, instead of renting attention from an algorithm. Everything else is borrowed ground.

That is what I mean by durable. Social and email keep shifting under you. The reach, the filters, what people actually see. You control almost none of it.

A website does not churn that way. It compounds. Someone clicks a link or follows a warm intro, and they land somewhere you built on purpose. Then they start sizing up how legit you are, based on what they find.

Subscribe now

The money is where it gets real. A six-figure overhaul is a hard sell when the current site works. It takes ticket sales. It processes donations. So a redo is not always the right call.

What tells you it is worth it is the gap. The gap between how the site portrays you and who you actually are. Small gap? Put your energy elsewhere. Wide gap? The site is holding you back, and you probably will not see it in your numbers.

Here is how I’d put it to a board. Your website is a player on your team. You would never let an employee coast on the bare minimum.

A website that is merely good enough is doing exactly that. Treat it like a real member of the team, one that shapes how people see you more than most. The question of whether to invest gets a lot easier to answer.

Episode Highlights:

[00:00:00] The website as your most durable, most controllable brand asset
[00:03:00] The identity impact gap, and when a redo is actually the wrong call
[00:04:30] Why “websites are dead” has been wrong for 20 years
[00:09:00] Transactional, informational, and storytelling: the competing flavors of a site
[00:10:30] The 10-second homepage test 90% of nonprofit sites fail
[00:12:00] Connecting the digital space to the physical space
[00:13:00] Brand as coherence: the Apple experience, and your version of it
[00:15:30] Getting to the brass tacks on a $100K investment
[00:17:30] What happens the moment a funder leaves your meeting
[00:23:30] What funders actually look for: financials, team bios, clear impact
[00:26:00] Your website should be your best fundraiser, not your only one
[00:28:00] The underperforming employee analogy, and the player on your team
[00:30:30] The garden: why a site needs pruning, not autopilot

Notable Quotes:

[00:05:20]: “I still believe that your website is your most important and your most durable asset as a brand.” Eric Ressler

[00:11:05]: “Most of those also aren’t very clear and they’re full of buzzwords. 90% of nonprofit websites fail that test, and that’s not even an exaggeration.” Eric Ressler

[00:12:20]: “We’re interacting with tens of thousands, if not hundreds of thousands of people online and they can’t all come here. So what is that warm, welcoming, inviting place that I’m sending everybody to?” Jonathan Hicken

[00:18:30]: “No one cares that you’re a nonprofit when they’re trying to buy a ticket. They just want to buy the ticket and they expect it to work just as well as checking out on Amazon.” Eric Ressler

[00:26:20]: “Your website should be your best fundraiser, not your only fundraiser.” Eric Ressler

[00:29:10]: “Website is almost the wrong word. It’s a player on your team.” Jonathan Hicken

Resources & Links:

• Seymour Marine Discovery Center — Jonathan’s organization, part of UC Santa Cruz

• Candid — nonprofit transparency and data platform, formerly part of what was Charity Navigator’s ecosystem

• Charity Navigator — charity watchdog and ratings organization referenced in the funder research discussion

• “Are Websites Dead?” — earlier Designing Tomorrow episode.

• Joel Breakstone interview — earlier Designing Tomorrow episode.

P.S. — Struggling to align your message with your mission? We help social impact leaders like you build trust-building brands through authentic storytelling, thoughtful design, and digital strategy that works. Let’s talk about your goals »

Full Transcript:

Eric Ressler [00:00:00]: I still believe that your website is your most important and your most durable asset as a brand. Your website, you do have full control over. If someone visits your website because they clicked a link or got a text message, you control the narrative, you control the experience. They are grading not only your website, but they are also subconsciously or consciously grading how effective and legit you are as an organization.

Jonathan Hicken [00:00:25]: I draw a correlation between the physical space that I have and the digital space that I have. And so one of the biggest arguments for me about investing in our website is we’re interacting with tens of thousands, if not hundreds of thousands of people online and they can’t all come here. So what is that warm, welcoming, inviting, exciting place that I’m sending everybody to go have that experience at?

Eric Ressler [00:00:45]: I’m Eric Ressler.

Jonathan Hicken [00:00:50]: I’m Jonathan Hicken.

Eric Ressler [00:00:50]: And this is Designing Tomorrow.

Jonathan Hicken [00:00:55]: Eric, I have a confession. I haven’t updated my website in five years. Now to be clear, I don’t mean updates. Obviously we’re changing events and stuff like that.

Eric Ressler [00:01:10]: Okay. My heart skipped a beat there.

Jonathan Hicken [00:01:10]: But we haven’t done shit with our website in five years. And every so often it comes back to my desk, “Hey, let’s update our website. Hey, let’s update our website.” And I keep kicking the can down the road. And so I want to spend today asking you some tough questions about why the heck I should spend the time and the money to redo the website.

Eric Ressler [00:01:35]: Okay. This could get spicy. Full disclosure, I sell websites for a living to some degree. So we’re at Cosmic, a design agency, a brand strategy agency, and a lot of times that work includes bringing the brand identity into digital experiences, the website, social, et cetera. So I’ve got a little bit of bias in this discussion, but I also believe really strongly that the website is still very important. I’m happy to dig into it.

Jonathan Hicken [00:02:00]: And full disclosure, I would love to find a way to hire you to do our website. So this is kind of like an informal interview on whether or not we should do this.

Eric Ressler [00:02:10]: Since we’re there, I’d love to read your website, man. Let’s go. So what’s stopping you? I want to hear why do you keep kicking the can down the road? You’ve got some structural issues, I think, but I want to hear it from you.

Jonathan Hicken [00:02:20]: At the end of the day, our website needs to inform people about when we’re open, which Google Business does for us most of the time. It needs to be a place where people can sign up for our programs and it needs to be a place where people can make financial transactions, buy tickets, become a member, donate, et cetera. It’s doing those things and it’s doing those things decently well. So why should I spend the six figure investment to make it world-class? Ultimately it’s kind of like I got more important shit to work on.

Eric Ressler [00:02:55]: What’s the ROI? Well, I guess what I would say is to put your particular situation aside just for a second, I don’t always think redoing a website is the right call. When people come to us, it usually is, but that’s because people are coming to us usually in some kind of transformative moment for the organization, some kind of pivotal moment. Either they’re starting a new org or there’s a new ED or there’s a new vision or a new strategic plan. And basically there’s this, well, we named it on the show a couple weeks ago, this identity impact gap, where their true identity as an organization and who they are and who they’re becoming and how they are representing themselves, how they are communicating, how are they perceived by their audience, there’s a gap there and that gap is a major problem. So if you’re in a situation where that gap isn’t very big, you should not redo your website. You should be focusing your efforts somewhere else. But if you’re in a situation where whether it’s the website or any other touchpoint for the brand is not aligned with who you are and who you’re becoming, then it is actually actively holding you back.

Jonathan Hicken [00:04:05]: Take us back a couple of years because we actually did an episode called Our Website’s Dead in 2024. So let’s set the scene a little bit. Set the stage on what you have seen the role websites playing back then versus now, how it’s changed, et cetera.

Eric Ressler [00:04:25]: So I think when I did that episode, that was actually season one when it was just me on the show.

Jonathan Hicken [00:04:25]: Oh damn. We’ve talked about website enough.

Eric Ressler [00:04:30]: We’ve talked about it before too, but the one you’re referring to, Our Website’s Dead. I was at the time thinking about that more because there was this narrative at the time that everything happens on social now and websites don’t matter, which I think is not true, first of all. I don’t think it was true then. Now there’s kind of this newer narrative being formed around like, well, everything’s AI now and people don’t even go to your website anymore, which also is not true, but it is a factor that now there’s a new technological shift and both those things are still happening. And despite all of those things being true to a degree, yes, a lot of brand expression happens through social or through email or other channels or in person. And yes, AI is eating up a lot of organic search, so less people are maybe coming to your website through Google, although that’s all changing, which I’m sure we’ll touch on. I still believe that your website is your most important and your most durable asset as a brand.

Jonathan Hicken [00:05:25]: What do you mean by durable?

Eric Ressler [00:05:25]: What I mean by durable is like social media and email to a degree even. They’re constantly changing. What’s in the algorithm? Who gets attention? Why? What’s popular? How are you perceived? You lack a lot of control. They’re not these owned channels. And email used to be kind of considered an owned channel and it’s becoming less and less of one as even emails have new filters and promotions tab. And just because you send an email to someone, certainly if it’s a promotional email, there’s no guarantee people are going to see that email anymore. Your website, you do have full control over. If someone visits your website because they clicked a link or got a text message, you control the narrative, you control the experience and that in a good faith way should be used responsibly to be authentic about who you are. It also means that anyone can spin up a website and spin a narrative that could be completely false, which we learned about when we interviewed Joel from Civic Online Reasoning recently. And one of the things he pointed to is people trust websites that look good. They trust websites that have an EDU or a .org domain, even though they might be a shell of a propaganda machine or something like that. So you can use that benefit responsibly. And I would argue that when people come to a website, they are grading not only your website, but they are also subconsciously or consciously grading how effective and legit you are as an organization. People come to the website and it’s a total mess. It doesn’t make sense. It looks poorly designed. It feels like some cousin’s second project. People start to wonder, rightfully so, is this org even legit? If they don’t care about how they present themselves in their most important asset, are they also kind of lame when it comes to their impact? So these are some of the things that I would think about. I’m happy to go more into true ROI on websites when done well, but even just at a base level, we just have to be pragmatic about if your website doesn’t look legit, people are going to judge you based on that, rightfully or not.

Jonathan Hicken [00:07:25]: So durability for you is about weathering time and you’re making a bet that websites are going to continue to have value no matter how the internet changes.

Eric Ressler [00:07:35]: People have been saying the website is going to die for like 20 years. Now lots of things are changing about the web and the internet and technology and websites have made major changes. A lot of people are experiencing websites on a phone instead of a computer now or they’re finding your website because they were researching something online and your organization got cited. So they might not even go to the website, but that website is still informing people about you and your work. And we have people coming to us right now who search for the best social impact design agencies and we come to the top of that search and they find us that way, not because they Google searched. Now I’d like to think that most of them go visit the website and look at our work and learn more about us, but some of them maybe don’t and they just book a call right away. The website still serves value in that situation because if the website didn’t exist and it wasn’t well designed and reputable, and by well designed, I don’t just mean visually well designed, but structurally well designed. The data was there for the AI search agent to find and to consume properly, then it wouldn’t have ever surfaced you in the results. So there’s all these intangible benefits to the website too.

Jonathan Hicken [00:08:45]: I wonder what you think about the sort of frame of mind, and probably every organization’s a little different here, so it might be hard for you to broad swath answer this question, but do your best. So there’s a frame of mind when we think about how we’re interacting with organizations online, we’re either watching a video on YouTube or seeing a post or a reel on social or now on AI we’re learning about it by asking questions of ChatGPT or Claude or whatever. What’s the mentality of somebody when they’re visiting a website that’s different from one of those interaction modes?

Eric Ressler [00:09:20]: So I think people come to websites for very different reasons. I think that’s one of the things that’s so hard about designing websites well is that especially in the social impact space, there’s usually multiple competing priorities. And then from your audiences that you’re serving, but even from your own team around what you want the website to do and what it should do. I have this kind of paradigm that I think about. Websites usually have some kind of flavor or series of flavors. So there are some websites that need to have some kind of transactional element. So for the Seymour Center, you need to sell tickets and that transactional element might be the only reason someone’s coming to the website and their experience of the website is going to be majorly influenced by how intuitive and frictionless that process was. And even that experience can have a major influence on their overall brand experience with the Seymour Center. But beyond that, in the best case, someone maybe comes in for a transactional experience but gets the best websites, you spend 20 minutes on it and you only meant to spend one minute on it, because you enter this experience and you find yourself wandering the halls of this digital space that’s so beautiful and so inspiring that you lose a sense of yourself and your time. And I think that’s what we aim for when we’re translating brand strategy into websites. There’s these transactional needs, there’s these informational needs, we have reports, we have resources, et cetera. There’s storytelling needs. I need people within 10 seconds to clearly understand my organization, who we’re for, how we help people, what we do. 90% of nonprofit websites fail that test. That’s not even an exaggeration at all. When people come to us, they might have their mission statement, they might have their vision statement. Most of those also aren’t very clear and they’re full of buzzwords. So we have a test that we run on website homepages, not that we hope people do this or expect people to, but if someone came only to your homepage and read only the first section of your homepage, they should be able to understand who you are and what you do and who you do it for. If they scroll through the whole homepage, they should be able to understand what other opportunities they have on the website and they should be able to understand a little bit more depth around the ethos of the organization, what you believe, what you stand for, your point of view so that if all they do is see the homepage and you test them, they basically get it. Again, most nonprofit websites and social impact websites egregiously fail that test.

Jonathan Hicken [00:11:50]: I draw a correlation between the physical space that I have and the digital space that I have on this. And sort of setting aside the integration of the digital and the physical for a second. When I think of people walking in our front doors, or actually even before they even enter the building, what they’re seeing on the outside, I want them to feel a certain sense of belonging or a certain sense of excitement about entering the space. And so one of the biggest arguments for me about investing in our website is we’re interacting with tens of thousands, if not hundreds of thousands of people online and they can’t all come here. So what is that warm, welcoming, inviting, exciting place that I’m sending everybody to go have that experience at? And for us, because we have a physical space too, even more power if we can get those two things sort of feeling the same.

Eric Ressler [00:12:45]: Right. And I think what you’re touching on there is something that I would basically just call brand experience. And when I think about building brands, there’s all these different places that your brand shows up. People think about brands as like your logo and your colors and those things are part of your brand, but really at the end of the day, your brand is, how did people feel interacting with your organization however they were doing it. If it was on your Google page, if it was on your website, if it was on your social feed, if it was in person, if it was at a closed door funder meeting, all of those are brand moments. And I think that in the best case and what you should be striving for is that there’s a coherence between all of those. And the best brands in the world do this amazingly well. A common example would be Apple. Apple is highly regarded as one of the best branded organizations in the world and you can criticize Apple and some of the moves they’ve made have been bad for sure, but you kind of know when you’re going to do anything with Apple, you’re going to get an Apple experience. And what does that mean? It means premium, it means effortless, it means beautiful, it means modern. Those are just the first four words that pop into my brain when I think about Apple as a brand, but it’s not because of their design in an aesthetic standpoint. It’s because of their human design. It’s what does it feel like to interact with an Apple product compared to a non-Apple product? I have my qualms, but for the most part, there’s a reason why they’re one of the most successful companies in the world. Social impact organizations are not Apple. They shouldn’t try to be Apple, but you need to figure out what your version of that is. What’s the Seymour Center brand? What’s the Seymour Center experience and how is it coherent between seeing you online on your website, coming into the front door and experiencing the center, looking at the latest Science Solutions Santa Cruz YouTube video. All of that should be a coherent experience that all works synergistically together.

Eric Ressler [00:14:40]: Hey friends, real quick before we continue today’s episode. I’m Eric Ressler, founder and creative director at Cosmic. Cosmic is a creative agency purpose built for nonprofits and mission driven organizations. For the last 15 years, we’ve helped leaders like you nail your impact story and sharpen your strategy, but we’re not here to just leave you with a fancy slide deck and a pat on the back. We roll up our sleeves and help you bring our ideas to life through campaigns, creative and digital experiences. Our work together helps you earn trust, connect deeply with your supporters and grow your fundraising and your impact. If you value the thinking we share here and want it applied to your biggest challenges, let’s talk at designbycosmic.com. All right, back to today’s conversation.

Jonathan Hicken [00:15:25]: The brand part of this, honestly, this is a strong argument. I instantly see the value of creating this consistent brand experience online and in person for us. To me, that makes a ton of sense. I think where I really start to get a little nervous is when I think about the actual dollars and cents of it all. So for me, I’m thinking about, okay, we need to convert X number more ticket sales in order to make the investment worth it, or we need to convert X number of members or somehow attribute a donor experience to actually closing a gift.

Eric Ressler [00:16:05]: Let’s get to the brass tacks here.

Jonathan Hicken [00:16:05]: Let’s get right into that because-

Eric Ressler [00:16:10]: Let’s pick a somewhat arbitrary number and let’s say a major website overhaul for an established organization is $100,000. It’s not always going to be that. Sometimes it’s more, sometimes it’s less, but just to make the math easy and somewhat realistic. So the obvious way to think about this is not as a cost, but as an investment. And so when you make any kind of investment, you are not expecting instantaneous returns. Unless you are buying a company or something and then you might get some short term wins no matter what the investment is. But some investments, like you think about stocks, you may lose your shirt on a stock for 10 years and then make it all back and then some 20 years later. A website should not be that, but the way that I think about websites, and again, when I think about the ROI and when the right time is, if you’re generally in a place of stability, a non-growth year, a subtle consolidation style year, it’s probably not a good investment for you, but the bigger that gap is between how your website is portraying you as an organization and who you actually are and who you’re becoming, that is a major, major, major problem that has all kinds of insidious and invisible issues. So it may not be something that you’re even aware of that it’s hurting you. Let’s make this real. You have a funder meeting, it goes great, you’ve been introduced, you’ve got a warm intro. What’s the very first thing that funder does after the meeting? Almost certainly.

Jonathan Hicken [00:17:40]: They’re going to go to your website.

Eric Ressler [00:17:40]: They’re going to go to your website. What do you want that experience to be for them? You want it to not just confirm the things they already know about you. You definitely don’t want it to be like, whoa, this is the same org that I just talked to that I was really excited about. This looks pretty janky. They don’t talk about any of the things on here we just talked about. Am I even on the right website? This literally happens sometimes. But really we want the website to help be this kind of always on asset for you that’s constantly working for you so that anytime someone comes there, it’s not only reinforcing the brand experience that they have in the real world, but it’s this whole other set of reinforcing experiences. So for the Seymour Center, let’s try and make this real. Yes, frictionless ticket buying experience. Those transactional elements need to be best in class, modern. No one cares that you’re a nonprofit when they’re trying to buy a ticket. They just want to buy the ticket and they expect it to work just as well as checking out on Amazon. When they search your website, they expect it to work just as well when they’re searching on Google. So you don’t get a pass just because you’re a small org. People have standards and bars that for better or for worse have been set by the world’s biggest tech companies that have hundreds of people working on making these experiences frictionless. So that’s the transactional side. But for the Seymour Center, now you have Science Solutions Santa Cruz. This is an amazing asset and it’s wildly successful already so early on. Why isn’t that on your website right now? Why isn’t that one of the first things I can learn about? Let’s say I’m searching here, I’m here for the weekend, I want to do something fun with my kids. I land on your Google page, I come to your website, I buy a ticket, I’m done. I’m not doing anything else in there. But what if I come and like, whoa, I didn’t know this about the Seymour Center. Holy crap, they’re doing all this stuff. Whoa, they have a whole podcast, and now you’re starting to build relationships with people. So yes, websites absolutely can hold you back, but often there’s also this kind of like, it’s good enough to do the job, which is kind of what I heard you say at the beginning.

Jonathan Hicken [00:19:35]: Which is pretty much exactly what I said.

Eric Ressler [00:19:35]: And that’s true. And so you need to decide at some point, whether it’s with us or someone else or whatever, when is the right time for you to make that not just good enough, but part of propelling you forward in the mission? And when you have all the right ingredients together, which to me would be like major growth or pivot opportunity or reinvention of who you are, new assets to work with like Science Solutions Santa Cruz that aren’t being utilized or just some kind of dissonance between how you are perceived through the website and who you actually are. To me, those are strong cases where yes, it’s a big investment of not just money, but also time and thought, but once you make that investment and you do it well, it compounds over time just like investing in any solid investment really.

Jonathan Hicken [00:20:20]: I’ll peel back the curtain a little bit and just be like, one of the reasons I have hesitated on moving to revamp the website is that the strategy that we have been developing and that we’re about to launch in a really big way here soon, I wanted to make sure that it was sticky. I wanted to make sure it was road tested. I wanted to make sure that what we were doing was going to fit, was going to deliver within our niche and I didn’t want to do a major transformation of the digital assets until I knew that that would stick.

Eric Ressler [00:20:55]: I think that’s a smart pragmatic move. And there’s a tension there because you don’t want it to be so late that you’re out there having those conversations right now. You got people excited about it and there’s probably people who you’ve met with who have heard about this who’ve come to the website and been like, wait, where’s the Science Solutions Santa Cruz stuff? Wait, this isn’t what Jonathan was just telling me about in the donor meeting we just had. So I could pick a pretty strong case that it is probably holding you back more than you realize. You’re still obviously doing great. We should also, since we’re just trying to be transparent here, you’re locked into a university system. And this happens sometimes with academic nonprofits and not only in that case where your hands are tied, you can’t revamp the website. There’s some creative things you can do around that to build alongside the main website and cross-pollinate. We’ve run into this before where orgs come to us and they’re like, hey, we want to build a really cool immersive impact report, but we can’t touch the website. What do we do? So what we usually do is we’ll spin up a microsite that sits on top of it or beside it in a subdomain or something. So there’s ways around some of those constraints, but that’s not really the true solution. The true solution is when possible to own the infrastructure and to not ever have tech be a reason why you can’t put your best foot forward as a brand. I understand in your situation and others, that’s a nice to have. It’s not something that you can always have full control over, but that’s a factor too.

Jonathan Hicken [00:22:20]: And I tip my cap to the university in a way because they’ve locked all of their entities into a certain set of templates because they’re trying to build a brand too.

Eric Ressler [00:22:30]: They’re doing their own brand building.

Jonathan Hicken [00:22:35]: Totally. And so now we have to respect that. We need to work within those constraints. But yes, that is a constraint that may be unique to my situation that others may have, but I don’t have totally free unbounded ability to build whatever I want, at least not in the way I’m thinking about it. And maybe that’s part of the reason why I’m hesitating.

Eric Ressler [00:22:55]: My gut level tells me that’s a big part of it because you’re just like, can I even do it? And feeling like, oh, there’s not only just the financial investment and the time and energy, but possibly even a political fight with the university or even just a straight up like, you can’t do it, man. I want to go back to this ROI conversation a little bit though, because I want to just even share for our listeners, we’ve had the privilege, I guess, or the opportunity to work directly with major funders and program officers and pick their brain around, hey, when you’re assessing an org, specifically on the website, what do you need? And we heard that across the board with everyone we’ve ever asked is like, how do you do research on orgs? And yes, they ask their peer funders and yes, they ask their network, but they also do their own research and they usually do it starting on your website. And we ask, what are the things that you want? And what we heard is a couple things. One, transparent financials, 100% needs to be there, easy to find. So we often will build out a section of websites that’s specifically for major funders that’s just like, here’s the checklist of everything you want. So they want financials and they want history of at least the last five years of those financials because what they’re doing is they’re saying, can this org absorb a gift of this size? Are they operationally ready and able to take this and turn it into impact? Do they have the right leadership team? What’s the pay structure? All that kind of stuff, their inputs for their decision making. So you want those financials to be super accessible, well presented, easy to find right off the bat. Some of these charity watchdog style organizations like what used to be Charity Navigator is now Candid, those can be nice signals as well that showcase some credibility and some transparency too, but you don’t need them as long as you are being transparent in how you communicate your things. So that’s one. The other thing is team bios, which I know can be kind of. We’ve been working with more and more orgs, especially in this state of play where people are concerned about even their staff being heckled or targeted in some way.

Jonathan Hicken [00:25:10]: Targeted in some way.

Eric Ressler [00:25:10]: Who are leaning away from full name or even photos on their team bios, which I completely respect. But in general, funders want to know who the team is and want to know who they’re investing in. And so when you feel like that’s a responsible move, I would highly recommend not just only having the leadership team and then just like everyone else goes away. Other things that we heard from some of those meetings is like, if you can’t articulate your impact clearly, if you can’t articulate your theory of change clearly, which does not mean a schematic diagram, but just like, here’s how we do the work and why your intervention is another way of thinking about that. What’s the way that you actually create impact? If you can’t clearly articulate in a way that makes sense in English who you are, who you do your work for that doesn’t require some kind of Rubik’s cube to solve, all those things are just creating friction and lacking confidence in an organization that actually knows those things and has clarity around it. So those are just some high level tips. I don’t want to diverge too much because I think we could do a full episode on this, but when we’re talking about ROI, to sum this up, your website should sell things for you. And what I mean by that is your website should be your best fundraiser, not your only fundraiser. Jonathan, for you, you’re out there having meetings and your website is your number two, because that’s the very first thing that people are going to do after having those meetings with you or even before in order to get the meeting in the first place.

Jonathan Hicken [00:26:30]: You know what’s funny is you helped me do this case for support and so what I’m trying to do is I’m trying to make that case for support the second place.

Eric Ressler [00:26:45]: It has to be.

Jonathan Hicken [00:26:45]: For us because the website’s not where it needs to be. So I’m like aggressively being, look at this first, this is the thing that’s going to bring home the deal or whatever.

Eric Ressler [00:26:55]: I think that makes sense. And I think in the best case you would have the case for support and then also the website would just reinforce all of the things you saw in there.

Jonathan Hicken [00:27:05]: What’s sort of occurring to me now is that there’s this hidden cost to having a website, which is for those donor experiences and they’re going to the website as a second place. I’m not seeing their drop off. I’m not seeing their thought process. That’s not getting back to me really in any way. I guess you could make the argument that I could probably track rate of closed deals and maybe attribute some of it to the website, but-

Eric Ressler [00:27:35]: But how would you know that’s the thing?

Jonathan Hicken [00:27:35]: There’s a million reasons why that could be the thing. So I think part of what I’m walking away with is paying attention to these hidden costs of this asset that is not where it needs to be.

Eric Ressler [00:27:45]: Have you ever had an underperforming employee who you know. So this is a good analogy. You’ve maybe had an employee or a coworker who’s clearly not pulling their weight. You know that feeling of just like, someone’s not pulling their weight, like they’re bringing the whole team down because of their energy or their lack of performance. Sometimes that’s the website, but the sort of more dangerous one is the employee who’s just kind of like checking the boxes who could be someone who’s doing so much more than that. And it sounds to me like your situation is more the latter.

Jonathan Hicken [00:28:25]: For sure.

Eric Ressler [00:28:25]: A lot of people come to us where they’re like, we know this thing is actively hurting us, help.

Jonathan Hicken [00:28:30]: Yeah.

Eric Ressler [00:28:30]: And maybe that’s right at some level. I would personally advise against waiting till it’s that bad, but you do have to have some kind of pain for it to be worthwhile. And I would say if you’ve ever had an experience with an employee like that who then gets replaced by someone who’s not just phoning it in, but who’s excellent and then you’re like, I could have had this the whole time. That’s kind of the experience we hear from clients we work with on websites where it’s just like, I had no idea.

Jonathan Hicken [00:29:00]: I actually think that’s a brilliant analogy and if you’re not using that with clients in your sales processes, you should because-

Eric Ressler [00:29:05]: I will now.

Jonathan Hicken [00:29:05]: Yeah. Because actually as you were telling that story, I was like, website is almost the wrong word. I know it describes the asset, but it’s a player on your team. And if you have a subpar player on your team, how do you as a leader deal with that? And a website is like doing work.

Eric Ressler [00:29:30]: And has almost an outsized influence compared to any one person on your team depending on the type of org that you are. We build websites all the time that have hundreds of thousands of unique impressions per month, per year. Very few staff members have that much influence over the perception of your brand. I’m not saying websites are more important than people, I’m just saying that they have a bigger influence on your brand perception sometimes.

Jonathan Hicken [00:29:55]: And just in my seat as executive director, that framing is like, this is a player on your team and how do you deal with average or low performers on your team? That’s kind of an aha moment for me.

Eric Ressler [00:30:05]: I think it’s a huge unlock in terms of how you think about it and I’d recommend to listeners they do think about it that way. And look, it’s a big move to do a major website overhaul and we really try to build sites in a way that you don’t do that over and over and over again. We actually had a client come back to us recently who we built their site over 10 years ago. They came back last year and we decided, you know what? We got to build it over. We very rarely do that because we are very intentional about we’re building it in a way that we can always be iterating on it. Another analogy I would use for the website is like a garden. There are times where you need to build the garden and there are times where you need to prune and a garden is only as fruitful as the effort and the time and the care that you put into it every day. If you build the most amazing garden in the world and you don’t water it and it doesn’t get sunshine or there’s disease or whatever, it will eventually fester and just become full of weeds and overgrown and eaten by critters, et cetera. And we see that basically same thing happen with websites. There’s a big moment, everyone rallies, they build the new thing. Sometimes it’s done well, often it’s not, and then it just kind of gets put on autopilot. You would never manage an employee that way. You can’t manage a website that way either. And the other thing I’ll just point to that’s another kind of intangible value about going through a website process is that it’s going to force you to make some tough decisions. And I would say this is true for any kind of brand, any serious brand effort. In order to build a good website, you have to know who you are, you have to have solid messaging, you have to have solid understanding of who the website’s for, who the audience is, what their needs are. All of that work either has to be done before or as part of a website overhaul in order for you to build something that’s going to actually be durable and serve the community and really be an asset for you. So hard work, but also work well done that’s going to serve you outside of just the outputs of the website itself.

Jonathan Hicken [00:32:05]: And that’s the fundamental premise of Cosmic’s work, right? Is that you enter at these moments of transformation and going through the process of building a website or a strategic plan or a case for support or whatever, you’re going to get into these hard hitting self-evaluative questions.

Eric Ressler [00:32:20]: Yeah. And look, I’m biased in that and that’s our approach, which is a great fit for some people and not a good fit for others. And frankly, I think a lot of times people are sort of scared away from websites is they’ve had one, two, three bad experiences. Unfortunately, many people who come to us come to us almost with past website traumas. And so we’re also part therapist who’s like, we will heal. It’s going to be okay. We’re going to get through this. And we know why that happened and we have a process to get around it, but there are absolutely people out there, agencies out there who are going to be happy to just do a tactical thing. Sometimes that’s what you need. I don’t think that I would usually recommend that approach unless there’s just something so fundamentally broken. You can’t get the budget to do it right and you got to just do an emergency stop gap. Every once in a while you got to do something like that.

Jonathan Hicken [00:33:10]: All right. Well, now you got me thinking about redoing our website here, buddy. So thanks for letting me grill you on it.

Eric Ressler [00:33:20]: I know a guy.

Jonathan Hicken [00:33:25]: All right. Thanks, Eric.

Eric Ressler [00:33:25]: All right, man, this is fun. If you enjoyed today’s video, please be sure to hit like and subscribe or even leave us a comment. It really helps. Thank you. And thank you for all that you do for your cause and for being part of the movement to move humanity and the planet forward.

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