Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs
Tailwinds is a project that brings momentum to the leaders tackling the world’s most impossible problems.
Created by Flying Whale Strategies, the show delivers ideas, insight, and energy to the people doing work that often feels impossible.
Each episode features brass tacks strategy that can be implemented tomorrow. Hillary Frances interviews social sector leaders who are in the messy middle of building their organizations. And since we are talking about bold solutions to intractable problems, she also brings in insight from the for-profit world.
Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs
How to answer the scale question
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Nonprofits are asked constantly to plan for scale, and most of us answer with ambitions to get bigger. But what if the right answer has nothing to do with size?
Hillary reframes the scale question entirely: scale isn't about growth, it's about influence. And sometimes the most influential thing an organization can do is change how it operates, not how large it becomes.
Hillary is joined by Sarah Cryder, Executive Director of City Kids Wilderness Project, who brings her own definition of scale to the table — one that has nothing to do with serving more people and everything to do with doing the work better. You'll hear them talk about:
- How to answer the scale question without promising to expand
- The difference between getting bigger and getting smarter — and why Sarah calls growth "getting fatter"
- How a shared staffing model with Outward Bound could change who gets to work in the outdoor industry
Not every organization should grow, but every organization should know what role it intends to play in the long arc of change.
Guest: Sarah Cryder is the Executive Director of City Kids Wilderness Project. She has an extensive strategic business planning and project management background. Prior to joining City Kids, she worked with local and national charter and district schools, foundations, entrepreneurs, and nonprofit service providers with a mission focused on improving education and life outcomes for underserved children. Sarah has also consulted with the D.C. Public Schools to implement evidence-based mental health intervention pilot programs, research successful national pilot interventions, and evaluate program outcomes through data-driven metrics. Sarah holds a Master of Public Policy from Georgetown University and a Bachelor’s degree from Boston College.
Mentioned:
Big Bet Bummer, Kevin Starr
Scale Really Matters, Kevin Starr
What’s your Endgame, Alice Gugelev & Andrew Stern
Stages of Startups, Y Combinator
Against Rushing to Scale, Randy Moore
My name is Hilary Frances, and one of the things I've been thinking about is how we should answer the question: what is your plan for scale? It kind of hits in the same way the question, "What are you going to do when you graduate?" used to hit, like a looming thing we need to know the answer to, but requires us to grow up faster than we'd like. We get asked this question most often by funders on grant applications or major donors. Sometimes we get asked by our board or our strategic plan consultants, and we think that the right answer is an ambitious answer. But lately I've been thinking that a good answer to the scale question is not that we're going to grow, it's that we understand how we are going to influence the problem our organization has been designed to solve, and sometimes that influence can be achieved by our same size organization working in different, more clever ways.
You're listening to Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs. Tailwinds is a project that brings momentum to the leaders tackling the world's most impossible problems. By the end of today's episode, you're going to have a clear idea about how you want to answer the scale question for your organization, and it's likely not going to be about growth. Today's episode has two parts. Part one, I'll help you talk about scale in a way that's meaningful to you. In part two, you'll hear pieces of my conversation with Sarah Cryder, executive director of City Kids Wilderness Project, who's been thinking a lot about this question for her organization and has a clever plan for scale without spending more money
So part one, this is really simple. Growth is linear, scale is exponential. We're shooting for scale, but to me, scale doesn't have to be a massive undertaking. I believe that you can still be an ambitious organization and not scaling in traditional ways. Scale is happening when we're achieving our impact goals through our influence. Scale is happening when our impact statements are coming to fruition because we've rallied others to work with us. So in one way you could say scale is achieved when we've created momentum for work that gets solved without us. Scale is an exponential relationship between inputs and impact. We used to have a linear relationship between inputs and outputs. One salary serves one caseload. With scale, now we have an exponential relationship. One salary impacts pods of other influencers, providers, school districts, city governments, groups of employers. Growth is linear, and that is what we've been trained to think about, how to get bigger and better. Growth requires more resources. You'll hear Sarah call it getting fatter. But I'm here to say that the problems we're trying to solve in the social sector don't need organizational growth to solve them, which would be larger institutions spending more money offering similar solutions to age-old problems. My favorite answer to the question: How are you going to scale your organization? Is this. Tell them that you're building a different operating system that allows you to deliver your solution more effectively. Often, scale requires a different operating system than the one we had when we were growing. So let's say you're doing land conservation. The way you do business now is that you have a team of staff and volunteers who are able to manage a limited amount of projects per year. If you were to operate a program that, say, paid for new staff to be embedded in the National Forest Service to manage projects through the Forest Service, you'd have broader impact much more quickly. This would be a public-private partnership and could be replicated across forest services nationally. So your answer to the question would simply be, "In order to move beyond the growth stage to a point of scalability, we know that we will need to change the fundamental operating system of our organization, and we're exploring options related to public-private partnerships."
Part two. Now I'd like to play clips from my conversation with Sarah Cryder. Sarah is on my board of advisors because even when I was working as her consultant, I was asking Sarah for advice. We first decided we were thought partners when we showed up for Zoom meetings wearing similar shirts week after week. Yes, I helped her team with big transitions, but Sarah helped me build Flying Whale. She's asked me questions like, "Do you really need to grow your business, or is it doing what you need it to do as is?" Or, Who do you need to work with who could take you to the next level? When I think of Sarah, I think about slow, strong delivery of clear information. She's the person you'd want to hear really big news from. She will not sugarcoat it, but she will not be anxious about it. She's also the person I think of when I want to channel being a woman carrying complex demands. I remember we were having a really lovely dinner in which we wore our favorite outfits and ordered everything we wanted, and she got a call from her children who were having a crisis at home thousands of miles away. She spoke with them and then said to me, they'll figure it out, which is exactly the type of way I want to handle the demands that are weighing on me. You need to know a little bit about City Kids Wilderness Project before we start. City Kids is working to solve the problem of BIPOC youth experiencing the highest rates of anxiety, depression, and suicide in recorded history due to the polycrisis of pandemics, climate emergency, systemic racism, and war. They're doing this through socio-emotional learning and outdoor experiences. They're based in Washington, D.C., but they operate there and in Jackson Hole, Wyoming. You'll hear Sarah has her own definition of scale, which is about operational efficiency and offering higher quality programs at the same time. Although she doesn't say it explicitly, I think she would probably say that City Kids is influencing the problem they're solving more effectively now due to the partnership she tells us about. Remember, scale is about influence.
All right, in this episode, we're helping folks learn how to talk about their plan for scale. And I'm arguing that often we conflate growth with scale. So could you describe for us what Citi kids looks like when you're operating a growth model one-to-one, and then what city kids would look like when you're operating a scale model One to many.
With growth, with your definition one-to-one, it by and large, creates the visual of actually just getting bigger. is getting fatter. You're actually having equal inputs as you are to outputs. know, and I, there are many times when city kids has operated in that way Some in smart ways and some in not so smart ways. And I can explain the difference with that when we're talking about scale. Because when we are in a growth model, one-to-one, it has been because we're at capacity with the existing resources, you need to get bigger in order to serve more or to do more. And I think a lot of that came, i, I will say in our history, I came on. As I came into City Kids as a deputy director, the former executive director, was working with half the amount of staff we have right now, as a result, we were a very program focused organization. All of the operational systems. Hadn't really been built. Built with real maturity meaning we didn't have robust program management systems. The use of other systems, like even development software systems had not been fully built out. And so because of that, we needed to bring in. people. We needed to bring in more systems in order to actually be able to grow the amount of that we were serving or the amount of programs we could offer, or with the systems, the way that we could actually track what we were doing as a program. That is when we decided to get fatter as an organization, we actually brought in more people. We had more things and it created an equal amount of output,
Yep.
You know, and I think that, that looked like having more programs as well. You know, the number of program days has increased over time. With scale, I actually think our recent time period at City Kids has been a time of scale, not in terms of the number of youth that we're serving, in the deepening of program that we can have. So a lot of the definitions of scale, you know, there's so many different ones. You know, the way that you're talking about it is, how can I give. A resource that creates operational efficiency that allows me to produce more when I've input. That's what I'm hearing when you, when you're saying that, and I, I actually think our greatest examples of that recently are as a result of adding director of strategy and operations at City Kids. We now tactically have one resource who has been able to then create multiple systems for volunteer management and program supply management, allowed us to think about our transportation operations in a way that now allows us to really optimize. How many kids can go on one single trip? How are we thinking about, utilizing operational systems to more effectively and efficiently and from a higher quality run our program? know, so that's kind of the internal piece for us operationally. The other type of scale that I think programmatically that has been really incredible and really, when I compare it to our earlier model where we got fatter, we grew to have more programs. Now I think we're approaching it more with a scale model of what you're saying, which is how are we bringing other people? In, we're bringing collaborative partners in to be able to do offer more of what we know is gonna make us have a higher quality program? City kids cannot, we're not big enough. We cannot afford hire We cannot afford to, it wouldn't make sense to have the expertise to, um, train everybody in sea kayaking, we wouldn't, or technical climbing when we climb the grand in Jackson, if we want to build social emotional curriculum and enhance ours, we can do that partly ourselves. But there are other partners who have an entire research wing around and department around this, so, particularly as the industry has shrunk, the outdoor industry has shrunk. It's become really critical for us to think about what are we uniquely good at that we can do, and then how do we work with other people to be able to scale impact? Um, in order to more effectively offer a high quality program, and that means not doing it all ourselves. It means finding partners with the skillset we don't have and asking them to join in. And also reflecting on what is it that we offer them in return. And I think, when we think about the one to many, it's City Kids is really good at youth development in the outdoors, particularly with brown and black populations. So because we're uniquely good at that, what other resources do we need to surround ourselves with and what can we offer them so that when we work together. Our whole is greater than the sum of its parts. And I think that's, that's a really important distinguishing piece for us between how we've grown, when we've gotten fatter, and now how we're scaling. And it really does include in people with different skill sets to us and working together.
Yeah, so would those other people be your partners in serving your kids that are enrolled in your program, or would they be serving their own kids?
So we're working to do, this is an answer that is both.
Okay.
I'll give an example. The partnership that we're working on with Outward Bound, for example, we are wanting affect change in the outdoor industry that allows more people of color work in the outdoor industry in a full-time capacity. City kids has seasonal workers, Outward Bound has seasonal workers. The challenge with seasonal work iss that it's seasonal in the sense that like it's not a year, always a year round job, and often because you're doing a series of day trips, when you're a trip instructor, you are offered a certain number, but it might not be a full week's work worth of work and often. A seasonal worker is, required to get a second job maybe in a different industry. So that can happen, eliminates a lot of people from being able to take it on as employment, which diverts to other sectors of work. If we want to be able to retain people in the outdoor industry, and particularly people of color. It's incumbent upon the industry to also create opportunities for people to have. Well paid full-time job opportunities in that industry. City Kids is working with another partner think about how do we create a shared and collaborative staffing model. In DC this partner is opening up a new site. We have in Washington DC we have our existing DC community, and we want. who do seasonal work for us to be able to work year round. And so we are working with a collaborative, in a collaborative partnership with the hope that we can offer a few days of work a week paid under our system and that. organization could take the same employees and give them the other half of the week, which doesn't cost City Kids any more money, and it doesn't cost the partner any more money because we were both planning to do that except now we've retained somebody in the industry because we have an alliance, a shared mission, shared youth, because we now will take our City Kids, youth and send them to the partner site. And so there's so much reciprocity what we gain from doing this. And in doing that, we are serving our existing City Kids, youth, then our city kids staff are also able to serve thousands of other youth because this partner organization serves thousands of youth. I think the industry blossoms because of it, and a lot of the reason why. We believe this isn't happening has a lot to do with capacity of an organization to actually just get outside of our own bubbles because we're working so hard, particularly in the nonprofit world, where your limited resources like prevent you often from having opportunities to think creatively, you know, outside of the box, you know? And I think that, um. We're really excited because, you know, we slowed down a little bit. We developed slow partnership over time, then we thought, now that we know each other, how could we make this something that feels bigger? it took just time for us to actually have space to say, what are the challenges you're facing in your organization? What are the challenges we are facing in our organization? And we talked about them. And took some time to actually think collaboratively about a PO potential solution. And so, you know, we're gonna pilot something because of that.
That's exactly what I mean by a different operating system. So the operating system of HR was limiting you. Your staffing model was limiting you, and so you are piloting a new operating system as it relates to staffing, and here we go.
In a industry, as I mentioned that is shrinking, where people are having to close different sites where. Funding is, is lowered in this moment to many of the social, emotional or foundational skill building, uh, organizations. You know, we're in a moment of time where we have to think creatively,
Yeah.
And so, you know, out of necessity we're trying to think about, um, what are some alternatives? And I think. In, in many ways that's the silver lining of it because we are now being really creative and I think it's actually an operational efficiency that will benefit us, not just in a moment, but for the long haul. And I'm really excited, you know, to do something like this just to see what we learn and where we go from there, and how we can also be a model for others. Assuming it goes well, but how we could also be an exemplar or a model for others on how to think creatively about your operating system and try something different.
I can imagine that there are donors who are very excited about funding your staffing system because it's so efficient and thoughtful and they get to impact multiple organizations.
That is the hope.
Yeah.
I think we're, we're, we're excited because we do have, initial donor who's interested in it, and I do think in conversations with many foundation leaders, many donors that. You know, it's not just unique to this industry. It's like we have a lot of duplicative systems out there. There's a lot of resources that, um, are provided that we might not optimize. And so I think that, if we can do more with less in a way that doesn't harm anybody, in fact might actually enhance what's happening. I don't know why people wouldn't be interested. In part of what I hope in this pilot time period is that we can figure out some of the nuance to it because there are, like the, the questions of when you get into the details, well, who's paying what and as insurance offered and benefits, and those are the pieces that make it, challenging sometimes to figure out like, when I actually wanna execute this. I do think if you approach things with a, how am I getting to? Yes. Instead of, how am I getting to, no, I think that's been critical. It's like, I wanna do this. I wanna see if it works. There are going to be details we have to work out and we're gonna hit some bumps. I'm positive we will, and I can either call it and not try it or. Try it and work at the kinks. And I think that, you know, to do something innovative, you just have to have a mindset that says, I want this to work, so I'm gonna do everything I can to make this work. And I think that's just the approach that I'm trying to take with some of these models that are, that we don't have many exemplars to follow in the industry.
Um, so. We'll see what happens.
Mm-hmm. Another piece of this puzzle in thinking about scale is the idea of your end game. And I wanna ask you about this concept of end game. It helps to talk about an organization's end game when we're talking about scale. So what do you think City Kids' end game is?
City Kids has operated 30 years on purpose, I believe that all the reasons. We have operated on purpose are going to be the reason that we will always operate on purpose, and so I would choose sustained service with the continuation to operate indefinitely on purpose. Because I, on purpose, believe that a sense of community, a sense of belonging, finding our own sense of personal power. Over long periods of time during adolescence will always, will always be important. And the piece of our organization that I hope one day is less relevant around equitable opportunity that we have that around systems that don't create barriers. I hope we eliminate those barriers that we're part of the solution around it. But the piece that's on purpose for city kids is around and I think that will, has historically, it is today and will always be one of the most critical parts of our ability to thrive, to feel somewhere. To be somewhere that we feel safe, somewhere that we feel like we belong and to be somewhere that we recognize we are one of many, and that is city kids in its essence. And those will always be important. And so, under my leadership and the historic leadership of this organization, and I hope its future leadership that the model will be sustained service, for, for those reasons.
Sarah's approach to scale is to build an operating model, staffing in this case, that allows City Kids to stabilize their workforce so that they can serve more kids. Those same staff members are serving more kids elsewhere This is a non-traditional answer to the question because it's not about having a broader reach or building a replicable model, and yet Sarah knows that City Kids is doing something really niche really well. Her response to the scale question is aligned with the president of the CD&R Foundation, who just wrote an article in the Stanford Social Innovation Review titled Against Rushing to Scale. He says that scale has become synonymous with legitimacy, and that not every organization is meant to be everywhere. He praises deep, high-quality, hyperlocal efforts. He says that, quote, "Choosing to serve one community deeply and consistently is not a failure of ambition. It is an act of discipline." Tailwinds is a production of Flying Whale Strategies, a consulting firm that is equipping teams to solve impossible problems. A special thank you to Sarah Cryder for sharing your wisdom and experience with us. If you want to learn more about City Kids, please look them up at citykidsdc.org. If you'd like to learn more about Flying Whale Strategies, please visit our website at flyingwhalestrategies.com. Thanks for listening.