A conversation with Stephen Halasnik of Financing Solutions and Dr. Lindsay Whorton 

Every nonprofit eventually reaches a point where the leadership skills that fueled its early success are no longer enough to support its next stage of growth. Building an organization requires one set of strengths. Scaling it requires another.

Strong nonprofit leadership requires more than passion. As organizations grow, executive director leadership must evolve from founder-focused decision-making to building systems, developing leaders, and strengthening nonprofit organizational culture.

On this episode of the Nonprofit MBA Podcast, Stephen Halasnik, Managing Partner of Financing Solutions (a leading provider of lines of credit to nonprofits), sits down with Dr. Lindsay Whorton, President of The Holdsworth Center, to discuss one of the most overlooked challenges nonprofit executives face: learning to lead a different organization than the one they originally built.

Their conversation isn’t about management techniques or productivity hacks. It’s about the personal transformation leaders must make as their organizations grow, become more complex, and create greater impact.

Whether you’re leading a startup nonprofit or an established organization, the lessons are remarkably consistent. Growth doesn’t simply require more resources or larger budgets. It requires leaders who are willing to evolve alongside their organizations.

Quick Answer

As nonprofits grow, executive directors must shift from doing the work themselves to developing leaders, building systems, protecting organizational culture, and thinking strategically about the future. Sustainable growth depends as much on leadership evolution as it does on funding and programs.

In This Episode

  • Why your leadership role changes even when your title doesn’t
  • The transition from founder to strategic CEO
  • Building leaders instead of solving every problem yourself
  • Why organizational culture must evolve as nonprofits grow
  • Hiring for future growth
  • Strategic planning for long-term sustainability

Nonprofit Leadership Changes as Organizations Grow

When Stephen Halasnik asked Dr. Lindsay Whorton how leadership changes as a nonprofit grows, she answered with a simple observation that resonates with founders everywhere.

“Your title stays the same, but your job is different.”

Many nonprofit leaders think becoming Executive Director or CEO is the finish line. Dr. Whorton sees it differently. Every stage of growth demands a new version of the leader.

During the early years of The Holdsworth Center, everyone wore multiple hats. Like most startup nonprofits, there weren’t enough people for specialized roles, so leadership meant doing whatever the organization needed. Fundraising, hiring, program development, relationship building, and daily problem solving all landed on the same people.

Those instincts were essential in building the organization. Eventually, however, they became limiting.

As nonprofits mature, leaders can’t continue solving every problem or making every important decision. Their responsibility shifts from doing the work to creating an organization where other people can succeed.

That transition isn’t simply operational. It’s deeply personal.

Many founders build their identity around being the person everyone depends on. Letting go of that role can feel like letting go of the very thing that made them successful.

Dr. Whorton acknowledged that she still misses parts of the startup phase. In a small organization, leaders know every employee, celebrate every milestone together, and experience the mission firsthand. The connection between effort and impact is immediate.

Growth changes that relationship.

Instead of creating impact personally, leaders begin creating the conditions that allow hundreds of others to create impact. Success becomes less visible because it comes through stronger people, better systems, and healthier organizations.

That shift is captured in one question Dr. Whorton encourages leaders to ask themselves:

“What systems can I build so other people accomplish more than I ever could?”

It’s a simple question, but it completely changes how leaders define success. Growth isn’t just about serving more people or increasing revenue. It’s about becoming the leader your organization needs for its next chapter.

Culture Can’t Depend on the Founder

One of the strongest moments in the conversation came when Dr. Whorton described how organizational culture changes as nonprofits grow.

When The Holdsworth Center was still relatively small, maintaining its culture felt natural.

“I knew everyone.”

She could personally welcome new employees, answer questions, reinforce expectations, and model the organization’s values through everyday interactions. Culture wasn’t something leaders talked about. It was something employees experienced every day because leadership was accessible.

As the organization expanded, that became impossible.

New employees joined. Additional layers of management developed. The informal conversations that once reinforced the culture happened less frequently, and Dr. Whorton realized something many founders eventually discover: culture doesn’t scale simply because the founder cares deeply about it.

“We had to think differently about how culture gets carried throughout the organization.”

That realization changed the organization’s approach to leadership.

Executive Director Leadership Requires New Skills

Rather than relying on the executive team to reinforce every expectation, The Holdsworth Center invested in developing managers who could model those same values within their own teams. Coaching, communication, accountability, and leadership development became just as important as delivering programs.

It’s an important lesson for growing nonprofits.

Mission statements don’t preserve culture. Leaders do.

Employees learn an organization’s values by watching how managers make decisions, give feedback, recognize success, and respond to challenges. As organizations become larger, culture becomes less about proximity to the founder and more about developing leaders who consistently reinforce the mission across every department.

Organizations that grow successfully don’t leave culture to chance. They build systems that allow it to thrive long after the founder can no longer personally influence every employee.

Build Leaders, Not Dependence

Throughout the conversation, Dr. Whorton returned to a common theme: organizations grow only as fast as their leaders do.

She referenced The Leadership Pipeline, a framework that has shaped her approach to leadership development. One of its central ideas is that every stage of leadership requires more than learning new skills. It requires adopting a new way of thinking.

Early in a nonprofit’s life, leaders are rewarded for being the expert. They solve problems, answer questions, and make critical decisions. Those abilities help organizations survive, but they aren’t enough to sustain long-term growth.

As organizations mature, success looks different.

Instead of asking, Did I solve the problem? effective leaders begin asking:

  • Did I develop someone else to solve it?
  • Did I build a better system?
  • Are our managers becoming stronger?
  • Is this organization becoming less dependent on me?

Stephen noted that delegation can be uncomfortable for nonprofit leaders because the mission feels too important to risk mistakes. Dr. Whorton agreed that letting go isn’t easy, but she offered an important reminder: if leaders never allow others to stretch beyond their current abilities, they also prevent future leadership from emerging.

Developing leaders requires coaching, clear expectations, honest feedback, and patience. It almost always takes longer than solving a problem yourself, but the long-term payoff is an organization that becomes stronger with every new leader it develops.

The goal isn’t to become indispensable.

The goal is to build an organization that no longer depends on one indispensable person.

Hiring for the Organization You’re Becoming

As leadership evolves, so does hiring.

Early-stage nonprofits typically hire for immediate needs. They need people who are adaptable, willing to wear multiple hats, and comfortable working in an environment where priorities can change overnight. Those hires are often exactly what the organization needs to survive its first years.

Growth changes the equation.

Instead of asking who can solve today’s problems, leaders begin asking who can help the organization succeed three or five years from now. Technical skills still matter, but so do leadership traits like adaptability, collaboration, and the ability to grow with the organization.

Dr. Whorton emphasized that hiring should reflect where the organization is headed, not just where it is today. Leaders who focus only on immediate needs often find themselves repeating the same hiring process every few years. Those who hire with future growth in mind create stronger leadership pipelines and greater organizational stability.

Growth also requires more intentional hiring processes. In small organizations, founders often interview every candidate themselves and rely heavily on instinct. As organizations expand, that approach becomes difficult to sustain.

Without shared hiring standards, every department begins developing its own definition of success. Over time, that inconsistency can weaken organizational culture and create very different employee experiences.

To address this challenge, The Holdsworth Center implemented more structured hiring practices built around shared expectations and organizational values. The goal wasn’t to eliminate flexibility. It was to ensure that every new hire strengthened the culture the organization had worked so hard to build.

As nonprofits mature, replacing founder instinct with repeatable processes becomes another sign of healthy leadership. Strong systems don’t replace culture. They protect it.

Think Like the CEO of Tomorrow

Toward the end of the conversation, Stephen Halasnik shifted the discussion from leadership transitions to strategic thinking. It’s one thing to manage today’s challenges. It’s another to prepare an organization for opportunities and obstacles that haven’t arrived yet.

For many nonprofit leaders, that’s one of the hardest parts of the job.

Board meetings, fundraising, staffing, compliance, and program oversight consume most of the workweek. Strategic thinking is often pushed aside until a crisis demands it.

Dr. Whorton believes that approach leaves organizations vulnerable.

One practice that has helped The Holdsworth Center stay focused on the future is scenario planning. Rather than assuming everything will unfold according to plan, leadership teams regularly discuss multiple possibilities and how they would respond to each.

For nonprofits, those conversations might include questions like:

  • What happens if a major grant is delayed?
  • How would we respond if demand for our services doubled?
  • What investments would we make if significant new funding became available?
  • Which priorities would we protect during a challenging financial year?

The value isn’t in predicting the future. It’s in reducing uncertainty before important decisions have to be made. Organizations that think through different scenarios are often able to respond more calmly, confidently, and strategically when circumstances change.

Stephen shared one leadership habit that helps him make time for that kind of thinking. Each week, he intentionally steps away from the office for uninterrupted planning time, often at a local coffee shop. It’s a simple practice, but one many nonprofit executives could benefit from adopting.

Strategic thinking rarely happens in the middle of a busy day. Leaders have to create space for it.

One Question Every Nonprofit Leader Should Ask

Perhaps the most practical insight from the conversation came from advice Dr. Whorton received from her board chair.

Rather than focusing exclusively on ambitious long-term goals, he encouraged the leadership team to ask a simpler question:

“Given our capabilities today, what’s the next best thing we can do?”

That question encourages disciplined growth.

Nonprofit leaders are constantly presented with opportunities, new partnerships, expanded programming, and innovative ideas. The temptation is to pursue all of them. But sustainable organizations understand that every new initiative requires people, funding, leadership capacity, and time.

By focusing on the next best step instead of every possible step, leaders make better decisions about where to invest their resources. Growth becomes intentional rather than reactive.

The most successful nonprofits aren’t built through one breakthrough decision. They’re built through hundreds of thoughtful decisions made consistently over time.

Leadership and Financial Sustainability

Although this conversation centered on leadership, it also highlighted an important reality: leadership and financial sustainability cannot be separated.

Growing organizations need strong leadership, but they also need the financial flexibility to support that growth. Hiring staff, expanding programs, investing in technology, and responding to community needs all require thoughtful planning.

Even healthy nonprofits can experience temporary cash flow gaps because of delayed grant reimbursements, government contract payment schedules, or seasonal fundraising cycles. Preparing for those challenges isn’t a sign of financial weakness. It’s part of responsible leadership.

Strong nonprofit executives think beyond today’s operating budget. They build reserves when possible, improve cash flow forecasting, diversify funding sources, and ensure the organization has access to working capital before it’s needed. That preparation allows leadership teams to stay focused on their mission instead of reacting to short-term financial pressures.
Organizations working with public schools face a sharper version of this challenge. As Dr. Whorton describes later in this episode, districts depend heavily on federal Title II dollars for professional development — funding that has been under active discussion in Congress. When state and federal money arrives on a different schedule than payroll, a school line of credit can bridge the gap without forcing programming cuts.

Key Takeaways for Nonprofit Leaders

Dr. Whorton’s experience offers several lessons for nonprofit executives leading organizations through periods of growth:

  • Accept that your leadership role will continually evolve.
  • Build leaders instead of becoming the person everyone depends on.
  • Protect your culture by developing managers who model your organization’s values.
  • Hire for the organization you want to become, not just the one you have today.
  • Make strategic thinking a regular discipline, not an occasional exercise.
  • Use scenario planning to prepare for uncertainty.
  • Focus on the next best decision rather than every possible opportunity.
  • Treat financial planning as a leadership responsibility, not simply an accounting function.

Frequently Asked Questions

How does nonprofit leadership change as an organization grows?

As nonprofits grow, executive directors spend less time solving day-to-day problems and more time developing leaders, strengthening culture, building systems, and thinking strategically about the organization’s future.

Why do founders often struggle during periods of growth?

The skills that help launch an organization, such as making every decision and solving every problem personally, become less effective as the organization expands. Sustainable growth requires leaders to delegate, develop others, and build systems that reduce dependence on one individual.

What is scenario planning for nonprofits?

Scenario planning helps nonprofit leaders prepare for different future possibilities by discussing how the organization would respond under changing circumstances. It strengthens decision-making, improves resilience, and helps organizations adapt more confidently to uncertainty.

How can nonprofits prepare for funding delays?

Organizations can strengthen their resilience by forecasting cash flow, maintaining reserves when possible, diversifying revenue sources, and securing access to working capital before temporary funding gaps arise.

Final Thoughts

Leadership is often described as a journey, but Dr. Lindsay Whorton offers a more practical perspective. It’s a continual process of reinvention.

Every stage of growth asks leaders to let go of habits that once made them successful and adopt new ways of thinking. The founders who build enduring organizations aren’t those who hold onto every decision. They’re the ones who develop people, strengthen culture, create effective systems, and prepare their organizations for challenges they can’t yet see.

As Stephen Halasnik’s conversation with Dr. Whorton makes clear, the most successful nonprofit leaders don’t simply build organizations. They build leadership capacity that continues to grow long after they step away from the day-to-day work.

That may be the most important lesson of all. Lasting impact isn’t created by one exceptional leader. It’s created by leaders who intentionally develop others, strengthen their organizations, and leave them better prepared for whatever comes next.

About the Experts

Dr. Lindsay Whorton, President, The Holdsworth Center
Dr. Lindsay Whorton is president of The Holdsworth Center, a nonprofit dedicated to building stronger leaders for public schools. She is the author of “A New School Leadership Architecture,” which calls for a fundamental redesign of how leadership roles are structured and practiced in schools, offering a bold new blueprint to make jobs sustainable and give teachers the coaching and support they need so that students thrive.

 

Transcript of podcast

00:20.02
Stephen Halasnik
Welcome, everyone. My name is Stephen Halasnik. I’ll be your host for today’s Nonprofit MBA podcast, and I am co-founder of Financing Solutions. And for the last 15 years, we’ve been the largest provider of lines of credit for small nonprofits in the United States. If you’re interested in learning more about a line of credit for your organization, please visit our website at nonprofitmbapodcast.com.

00:45.02
Stephen Halasnik
dot com Today, I’m very excited to be speaking with Dr. Lindsay Whorton from the Holdsworth Center. um Today, we’re going to be talking about founder to senior executive director, how Lindsay has what she’s learned ah in building a nonprofit that started from so scratch and now is at a $30 million dollars mark.

01:11.61
Stephen Halasnik
And we’re gonna be kind of focusing a little bit more on the skills that that she’s learned that are important um to help an organization grow. ah Dr. Lindsay Whorton, as president of the Holdsworth Center, a nonprofit dedicated to building stronger leaders for public schools, She is the author of A New School Leadership Architecture, which calls for a fundamental redesign of how leadership roles are structured and practiced in schools, offering a bold new blueprint to make jobs sustainable and give teachers the coaching and support they need so that they can so that their students can thrive. Lindsay, welcome to today’s Nonprofit and MBA Podcast.

01:56.34
Lindsay
Thanks so much for having me.

01:58.33
Stephen Halasnik
So I’m going to jump right into the the deep end here. And if you had to have like a one sentence to describe what you are like now as an executive director from a skill standpoint versus where you were when you first started, what what would you say ah that it is?

02:18.36
Lindsay
Well, i I think my sentence would be your title is the same, but your job is different. And the pace at which you are getting a different job with the same title um as you move from a brand new organization to a much more established, large organization is a really rapid um change. I don’t even know if I could compare in one sentence the job I have now to like my first job. But I think there are these kind of chapters where you have to constantly reinvent how you think about your role um and and revisit

02:53.30
Lindsay
where you need to be spending your time, the skills you need to develop and like the mindset, you know, you need to bring to your work. So I think that has been kind of the challenge and what keeps it so interesting, even though you you’ve hypothetically got the same job.

03:06.90
Stephen Halasnik
Do you miss those days when you were doing the founder’s work?

03:12.19
Lindsay
I think in one background I’d get, so the background I’d give just to give some context, You know, I i met ah the person who had the vision for organization, Charles Butt. He’s a big advocate for public education um in 2015.

03:26.97
Lindsay
And my first job was actually just to help him put together like the business plan and the strategy for what this thing could be. You know, and I thought I was just going to do that and kind of leave it in his hands and go on and do something else. and He convinced me to move to Texas and, you know, I had my first job at the organization. We started serving about seven school districts. We had a team of about 20 in 2017. And then i moved into the president role um in 2019. And it still had a lot of kind of small startup new energy, you know, when I moved in to that role. and I think what I’d say is there’s something really ah beautiful and special about like each chapter, um of an organization’s life. And there are things that I loved, um, about those early days. Um, and there’s lots of like great opportunities, um, in the new chapter. So I think it’s like a both end of like, I really appreciate that and really,

04:22.49
Lindsay
ah feel excited about like where we are now and i embracing like the opportunities that like this chapter in this season brings.

04:30.17
Stephen Halasnik
Yeah.

04:31.22
Lindsay
But it’s easy it’s easy to get nostalgic, ah you know, for for for for like when you’re smaller and like, and I think that nostalgia ah can be a bit of a, can be a bit of an enemy.

04:34.14
Stephen Halasnik
Yeah. Yes.

04:42.15
Lindsay
So i think you got to be a little bit careful about that.

04:44.34
Stephen Halasnik
Yeah. I mean, me personally too, going from, um, you a various different companies, founders, a founder at various different organizations or companies, and then, you know, and then building it to a much larger organization,

04:58.58
Stephen Halasnik
ah The nostalgia, I agree with you, ah but i I do feel like once the organization is much more established,

05:09.27
Stephen Halasnik
You can breathe a little more, you know, it’s, it’s a little bit more, you get to work on things instead of working in the organization so much.

05:17.24
Lindsay
Yeah.

05:18.69
Stephen Halasnik
And that’s, you know, I think most founders are trying to get out of being the early startup phase where they’re doing everything.

05:28.76
Stephen Halasnik
Is that fair to say?

05:30.81
Lindsay
Yeah. I think it’s funny. the The book that I wrote about school leaders um and draw some inspiration from, ah a book we use in our program for a long time called the leadership pipeline. i mean, I think it has this really ah powerful framing of shifts that leaders need to make as they move through their career. And they talk about like three different kinds of shifts. One is like, what are the new skills you need to either develop or lean into and use more um as you shift the others? How do you need to spend your time differently? But the third, and it’s like the hardest to pin down, but i actually think it’s the most important is where do you need to have shifts in your professional identity? And I think a professional identity is like the highlight reel that you have at the end of the day about like the great things that you did and the way that you made a difference and the stuff that makes you feel good about yourself.

06:19.22
Lindsay
And I think when organizations are small and when you’re in kind of that scrappy startup mode, you’ve got your hands in everything. um And like for us, i mean, we’re a ah service organization. You’re getting to interact like with people that you serve all the time. And it’s like so rewarding ah to to be the person doing the thing and delivering the product or delivering the service.

06:40.18
Lindsay
And I think that when people get so attached to that form of value, it can be hard to transition into the new roles that you need to play, which is creating the conditions for other people to be able to do the work.

06:52.86
Lindsay
And so I think what trips people up is that um values attachment ah that you have to how good it feels to kind of be in the center of everything. um but But to your point, there is this like extraordinary other opportunity, which is if if you can do your new job, um if you can help create conditions that allow the organization to serve people well at a greater scale, and which requires you to set up other people to do that work, then you get this reward of like how remarkable it is that the organization can take on new challenges, that it can, like all the things the organization can do um kind of become the reward.

07:05.60
Stephen Halasnik
you

07:34.92
Lindsay
But I think it takes like real work for leaders to to let go of some of the things that have been so rewarding and valuable to them about those early stages, and then give themselves time and space to find value in in new things.

07:50.07
Stephen Halasnik
You talked about control, but going from um the you know the early stages of the nonprofit, what did you have the most difficult with that as ah as as your characteristic traits, so to speak? I can’t think of a better word than that, but ah your skills.

08:11.80
Stephen Halasnik
um Where did you struggle the most going from a smaller organization to a larger organization? What was difficult for you?

08:21.50
Lindsay
Yeah. I think there were probably two big things for me, one of which doesn’t have that much to do with size, but just has to do with like my own personal leadership journey and the kind of evolution of the organization.

08:36.92
Lindsay
i was really… I really loved like kind of being in like a number two role. um I got to do all the things I love most, you know, which was like really think about the work, think about the strategy, think about how how to make like the work and the impact better. um And I also was very like down and in, you know, in the organization. I was thinking about our people and I was thinking about like the people that we served.

09:03.70
Lindsay
And for me, the transition to taking that responsibility for being up and out, you know, was, was a big transition. and coming to really find value in ah feel confident in, and really dedicate time ah to to building the organization’s brand and reputation for being visible in different places, for using you know my my voice in the world. That that really was a big transition for me because I’m not somebody who seeks out you know the spotlight. And I but i was really lucky to have a board

09:42.10
Lindsay
that had incredible incredible seasoned leaders from a bunch of industries who really challenged and encouraged me and just kept the thumb on the scale of like that expectation. And that was really critical for me to really make that transition. So that was one. and then I think the second is like when we started, know, we had 15, 20 people in like 19 of them ah were program people, you know, were folks who were doing the work

10:12.28
Lindsay
And most of your like back office um functions, like IT, HR, finance, you know, all these things either just didn’t exist um or were like outsourced and we were small enough where that could work. And so the process of bringing in all of those important support functions and and getting the them to work in concert with our programs and then not become a really bureaucratic organization Like that has been like a big curve that we’ve been on, you know, for the last um four to five years. um and And I do think that especially if you’re somebody who got into this work through kind of the mission, the strategy, the program, the product of the organization, building the knowledge that you need um and and coming to appreciate the importance of all the work you need to do to set up those systems and processes, I think is a big leap.

11:06.87
Stephen Halasnik
If you were to think of an inflection point, let’s say when you went from $3 million to $10 million in revenue, yearly revenue, you know so ah it doesn’t need to be that, but you know a big – can you point to one of the top things that helped you make that leap?

11:17.53
Lindsay
you

11:26.36
Lindsay
For me, I actually think the inflection points that I measure were all about our headcount. um So that’s how I felt. and And obviously that’s highly correlated, you know, with with revenue because staffing is, you know, a huge percentage of our budget. But we we went through a period where we basically doubled in size um twice in like a three year period. So we went from like 20 to 40 and then we went like 40 to 60, 60 to 80 pretty fast. um And that happened during COVID um for us. And to me, because like our mission and strategy is all dependent on like the quality of the people that we hire, their alignment and like the culture that we have as an organization. that’s where I really felt kind of the, that transition. Um, because for me, what I noticed is the way that I had engaged, tried to build and tried to sustain the culture when we were 20 people was dramatically different, uh, than what that needed to look like when we were 40, 60, um, 80. And eighty and i eventually realized that the shift that had happened is when we were 20, I could almost,

12:35.90
Lindsay
maintain the culture through my own personal one-on-one relationships i’m with everybody. And as we got bigger, and then as our context changed, you know, through COVID and different ways of working,

12:48.15
Lindsay
had this realization of like, I could not personally um be the carrier of the culture of the organization anymore and really had to figure out how to make sure that every manager, you know, that we had in the organization was equipped and ready to do that work. Otherwise we were really gonna lose ground in terms of some of the things that made us great. And so that’s where I really experienced kind of the big shift in that chapter. And then I would say for us, um there was a second big shift, which we had kind of plateaued. We had kind of leveled out in terms of our kind of

13:28.50
Lindsay
staffing model, our overall revenue model. But then we made this other big transition, which is we went from having one main kind of, for us it’s a program, one main product that we were scaling to then diversifying and offering kind of more products and services. ah And that was another big change um in the organization of like, how do you um help the organization understand the strategy as you are now doing more diverse and more complicated um things. So that’s the second place that I think we really experienced that.

14:02.82
Lindsay
Okay.

14:03.19
Stephen Halasnik
Did you find that… um I know with me early on I had to learn better how to hire people, how to hire the right people, how to set expectations correctly, have how to have job descriptions, how to have an identified culture in place so they knew you know the culture of organization.

14:27.00
Stephen Halasnik
Did you find that you did a good job early on in hiring or was it a learning experience for you too?

14:35.26
Lindsay
I think it’s a both and. I i think we did a very good job from the beginning of investing time and energy in finding and retaining the best people that we could from the beginning.

14:53.98
Lindsay
um I think that was probably one of the things that we got right. um I think one of the biggest challenges that we had in hiring, honestly, and I don’t I don’t totally know what the solution is to this. what What I experienced is that jobs, it it isn’t just my job that was changing, you know, over the last like 10 years, but particularly when we started, you know, we hired somebody to do something in 2017. And what we needed the person in that position to be able to do two years later or three years later was actually dramatically different.

15:26.33
Lindsay
And so I think the biggest mistake that we probably made early on was hiring for like the needs of the moment. You know, like what exactly do we need this position to do for the next six months?

15:37.50
Lindsay
And not being able to see honestly well enough, like what do we need this position to to grow into over the next two to three years? And I think that was the biggest challenge for us at the beginning.

15:50.26
Lindsay
there There was a point where, and it was about five years in, and this is related to size. Early on, I was involved in the hiring of every single person who joined the organization. And that and and I have my own flaws and limitations. So it’s not to say that I’m a perfect hirer, but you had some consistency in how the process ran, what you were looking for, um how you thought about kind of skills and mission alignment. And when we got big enough, I reached this point where I realized it is not sustainable for me to play that role in hiring. And we didn’t do a great job initially of really being explicit about what needed to be true in our hiring processes as they were held by more people.

16:36.66
Lindsay
And so after about kind of a 12 or 18 month period, we recognized that we were maybe a little too inconsistent and we’ve put a lot more effort into really codifying um from beginning to end how we want hiring to work at the organization. And that allows more people ah to be a part of that process and get a consistent outcome. And so that was the other kind of key lesson for us.

17:01.40
Stephen Halasnik
What was the big jump in revenue? why What was the cause?

17:06.33
Lindsay
For us, our our increase in revenue has just matched an increase in service. You know, so we, when we started in 2017, we had a pretty robust five-year plan because one of the things that’s really unique about our organization I feel really lucky for, we had a two-year planning period ah before we started.

17:24.91
Lindsay
And so we had kind of five-year roadmap, the details of which, you know, nothing nothing plays out exactly according to your plan.

17:25.18
Stephen Halasnik
Hmm.

17:33.44
Lindsay
But honestly, the the kind of revenue projection, we ended up hitting it pretty close, you know, through our first five years. And so we had a plan when we started to say we’re going to start relatively small, you know, with seven districts.

17:46.47
Lindsay
And then we we had a kind of scaling plan in place that was that was matched with our with our revenue um and costs. and so So for us, it was really just like we had a plan to grow the organization and we executed that.

18:00.76
Lindsay
um

18:01.23
Stephen Halasnik
So…

18:01.72
Lindsay
we We had to make some adjustments to our scaling assumptions. ah There were a lot of lessons learned and there. But then I think once we got kind of to the end of that five year period, we started asking questions around where we go from here. And that’s where we started to kind of diversify our programming. And we grew kind of beyond the the original forecast that we had had when we launched the organization.

18:25.85
Stephen Halasnik
if ah so If you’re, let’s say you have an executive director listening today whose organization is like around $500,000 to a million dollars or a couple years into it.

18:32.30
Lindsay
Yeah.

18:39.54
Stephen Halasnik
um And they’re a new executive director. They’re, you know, not new to or they’re the founder and the or the executive director. And they, you know… You know, what advice, knowing what you know now, i know you don’t know the the nonprofit, ah that that their own particular nonprofit, but in general, what’s the advice you would give to that person?

18:55.26
Lindsay
yeah

19:06.82
Lindsay
I’m a big um believer. I believe that long-term planning is useful, not because your long-term plans are correct, but because it gives you ah better ideas about what you might do. um It makes you better at anticipation um and it makes it easier for you to respond to opportunities you know as they come your way. And so I’m a really big a believer I believe if you’re the head of an enterprise, it’s your responsibility to be thinking on a three to five year time horizon perpetually. And I think if you’re brand new into the role, you may you’re probably not going to get to three to five years right away. I think that’s okay. You know, you may have like a a short term list of things you just kind of need to get done. But eventually i think you should be constantly refreshing, like your vision of what three to five years could look like. um And I,

20:02.23
Lindsay
think it’s really useful to to think in scenarios, you know, to say like, what would what would kind of be our, like my most aggressive, you know, in terms of scale, growth, revenue version of what the organization could look like, you know, would be a moderate version. And then what would be like my worst case, you know, scenario, you know,

20:21.27
Lindsay
And one, i think it it it it can help you refine your sense of like what is actually possible. It can help you think through like what would need to be true, you know, in my organization for us to operate in a scenario, B scenario and C scenario. and and a lot of times you’re going to discover some things that are in your need to be true list that are common to a, B and C. And those are things you should certainly start doing, you know? Um, so I just think carving out this time, to think long-term and not feeling a pressure that, that your planning has to be right, you know, or that you have to know everything, um, in order to develop your plan, but really thinking kind of probabilistically, um, and in scenarios, I think is really energizing, ah

21:06.84
Lindsay
for executive directors or CEOs. And I think it it makes you far more creative, far more agile um in how you do your work. And I think that’s the biggest thing we sometimes get wrong about planning. I think some people do planning in a way where it’s like, and then once I develop the plan, I’m like locked into that plan, you know, and the plan makes you rigid and it makes you unresponsive. And I think there’s a different way to think about planning. Yeah.

21:31.90
Stephen Halasnik
Yeah, I think ah if I look, you’re right. um I think I do that too. i I think, but you said something before that might stop one from doing that. And it is if you come up with different scenarios, right? If you come up maybe with, you know, if this happens, you know, what would our plan be? like You know, ah if if this happens, you know, maybe if you don’t,

21:58.42
Stephen Halasnik
think of the goal first, ah it doesn’t lock you in as much. um I completely agree you know with strategic thinking. you know i always I would almost take every…

22:10.78
Stephen Halasnik
every week for about an hour over a cup of coffee at a coffee shop, typically to kind of go over my strategic plan. And for me, it always have to be in writing just so that I can kind of understand and update and see where we are and make changes and those types of thing.

22:28.68
Stephen Halasnik
And I honestly, I love that hour, hour and a half. it was one of my favorite things to do, you know, um,

22:32.61
Lindsay
you

22:36.25
Stephen Halasnik
So i i usually ask this in the beginning of every conversation um for the last two years, um but ah I forgot to ask it and i’m going to bring it up now.

22:47.77
Stephen Halasnik
How has this current administration affected your organization?

22:57.75
Lindsay
So we’re we’re based in Texas um and we’re ah focused on Texas public schools. um And so when we think about like the conversation around public education, like across the country, there’s there’s a lot of things as I interact with my colleagues, like across the country, I think there’s a lot of things that have felt new to them,

23:16.35
Stephen Halasnik
you

23:18.26
Lindsay
ah when the administration came into office a few years ago that were already true um in Texas. you know And so in in that sense,

23:30.42
Lindsay
there wasn’t as much that that felt different. um we We also um are not, our our funding sources are not, we don’t take it we have not taken any kind of federal government um grants um and And we don’t rely significantly on government grants of any kind. And so i think that probably has buffered us some from the from some of the turbulence and change, you know, that that has happened in the sector. Probably that the biggest thing that’s on the horizon for us is and this is this can get a little in the weeds, I’ll keep it. You know, but there are some changes being contemplated to the funding that a public schools receive from the federal government through title dollars, you know, in particular. um And if some of those sources of funding become unavailable, those are the sources of funding that districts use to pay for professional development and all sorts of other services. And so I think the big thing that we’re trying to do is understand how the districts and schools that we serve are being impacted you know by some of the shifts in policy and in funding. And then we just have to figure out how we’re going to be responsive to that. But we’re we’re a little bit less um directly connected to some of the changes that I think are impacting you know other other nonprofits who may rely more significantly on government grants.

24:57.02
Stephen Halasnik
I’m going to put you on the spot here.

24:58.51
Lindsay
Yeah.

24:59.61
Stephen Halasnik
We talked about planning. um Have you gone through this scenario if that funding for title had, I don’t know if it’s Title IX, know if it’s something else, Title II.

25:11.80
Lindsay
It’s title two, title two is the big, yeah.

25:13.94
Stephen Halasnik
So Title two if it does go away, um have you gone through that scenario?

25:19.10
Lindsay
Yeah.

25:21.92
Lindsay
Yeah. Yeah. So we do both, I mean, our planning cycles in the organization, we basically have like an annual cadence where we kind of do long-term planning and then we do a lot of sprints, you know, around scenarios. And so the summer of 25,

25:37.28
Lindsay
their Congress was having discussions about potentially eliminating or significantly reducing Title II dollars, which are these dollars that districts use to pay for professional development, et cetera.

25:48.47
Lindsay
um And so we went through a scenario of like, what if those dollars completely go away? And what if, and what if they go away on this timeline versus this timeline versus this timeline, what would we do in response to that? And so we, we built out all those plans. We didn’t end up needing to make any, any major adjustments to what we were doing. But again, it increases anticipation and like, responsiveness So every time we kind of see something like that on the horizon, ah we kind of go through a process of thinking through what our actions would be.

26:25.86
Stephen Halasnik
Cool. Got it um the ah

26:31.38
Stephen Halasnik
what is What is something that keeps you up at night right now?

26:36.89
Lindsay
my answer to that which is always the same and then i’ll try to think of i mean honestly and i think this is probably true for almost everyone in in every sector of kind of the nonprofit space.

26:49.34
Lindsay
There is, when we think about public education, you know, there are wonderful things happening for kids in public schools every day. And we need to tell those stories more. And we have so much work to do, you know, to make schools,

27:02.84
Lindsay
ah places that consistently for every kid provide them with an experience where they feel joyful coming to school, where they feel belonging and where they get what they need, you know, to have this the skills that they need to unlock their potential and to live great lives. like we have so much work to do and we have so much work to do to make schools ah places where the teaching profession is like vibrant and sustainable and attractive.

27:25.98
Lindsay
And so I’m really like proud of what our organization is doing, but there isn’t like a day or a week that goes by where I think like we did enough, you know? Um, Like there’s always a gap but between the need and the importance of the work and like what you’re able to do like each week or each day.

27:36.06
Stephen Halasnik
Mm-hmm.

27:43.14
Lindsay
and I think learning to live with that sense of like perpetual dissatisfaction, you know, is the challenge. Because on one hand, like if you dialed it all the way down, you’d like feel better.

27:55.21
Lindsay
um But you wouldn’t have like the right motivation and energy and sense of purpose to come to your work. um But also if you allow it to just like burn you up, you know, then you can’t sustain yourself and and and you become discouraged.

28:09.60
Lindsay
And I think our first board chair was Ruth Simmons, who’s an just acclaimed higher education leader. and like one of the pieces of advice that she gave me that I have just found so helpful is like in every moment and every opportunity, you just have to figure out like, what are you good at?

28:28.15
Lindsay
What are the capabilities that your organization has? And like, what is the next best thing that you can do, you know, in response to the need that exists? And you can’t get overwhelmed ah with with trying to answer the question of like, whether it’s enough, you know, to tackle like everything that you’re seeing, you just have to figure out what that next step is.

28:46.00
Lindsay
And I think that’s been like a really good anchor.

28:46.21
Stephen Halasnik
Mm-hmm.

28:48.92
Lindsay
i think probably the timely version of that is I do feel really worried about, um it It feels like we’re, I mean, I think there’s so many fractures across our country. There’s so many things that used to be points of common agreement, you know, that are now divides. And I think public schools are one of those things. You know, i think that’s an area that where we’ve had common agreement for a really long time. And it feels like common agreement around public schools being important. Um,

29:21.18
Lindsay
how we should invest in them is really fracturing. And and I do worry about that. and I think, you know, we all in that space have to figure out what role do we need to play in rebuilding trust um around our public schools and like making them, you know, a place that we can rally rally around across the country.

29:39.35
Stephen Halasnik
what What is the number one thing that you the teachers, like so every state has a different culture.

29:45.55
Lindsay
Yeah.

29:45.69
Stephen Halasnik
So in Texas, from what you’ve seen is, and I’m sure it’s part of your your programming for leadership, ah what are the number what is the number one thing that teachers in Texas, which are you know saying to their leaders, um ah is their biggest concern?

30:10.36
Lindsay
I think it’s hard to come up with and a number one thing. um

30:13.32
Stephen Halasnik
Mm-hmm.

30:15.04
Lindsay
I’ll give you like a handful. um So, I mean, I, one, i do think ah

30:26.33
Lindsay
teachers are leaving the profession for a variety of reasons. um But i I think you can boil down a lot of the reasons why teachers leave to to them basically saying like, I care deeply about um about this mission that I’m trying to accomplish. And i don’t feel successful um on a daily or weekly basis. you know I don’t always feel like I’m given the tools, the resources, the time, the support that I need to achieve the goals that I’m being tasked with.

30:54.87
Lindsay
And I think when you’re a mission-driven person, if you feel like you are not able to achieve your goals, I think that just like eats away you. know at you um and And so I think if you kind of break that down I don’t think we provide our teachers with like enough ah support, training, encouragement, time within their day to like think deeply about their practice, to prepare. I mean, US teachers spend more time delivering instructions to students and less time on like planning, collaboration, than almost any other teachers around the world. And I think that is is getting more challenging in our post-COVID environment. You know, teaching is one of the most regimented, you know, jobs that you can have. and You’re driven by bells. You’re on this really tight schedule. I mean, teachers a lot of times, like, getting to the bathroom’s challenging. You know, getting to have time for lunch is challenging. When we think about knowledge workers and all the flexibility that so many knowledge workers have, you know, we’ve got to figure out how to give like more flexibility, more autonomy, more room to breathe, you know, uh, to our teachers, um, pay, uh, can certainly, uh, be better, um, and, and, and should be, should be better, uh, for, for our teachers. Um, and then, you know, I think that their teachers feel it when teaching and education is at the center of our political debates.

32:24.25
Lindsay
Um, I don’t think, i think you feel you feel challenged, you feel distrusted, um you don’t feel supported ah by your community. And I think the sense that people are suspicious um of you um or don’t think highly of you, i think wears wears away um at people.

32:43.06
Lindsay
And so, i mean, I also think just like lifting up teachers and and and giving them the respect and honor that they’re due would be like my five.

32:51.21
Stephen Halasnik
Yeah. Yeah. I mean, for my, I have two sons. So for me in New Jersey, I’m i’m in New Jersey ah and in New Jersey has excellent school districts. um And they ah it’s, to me, it’s a morale.

33:08.06
Stephen Halasnik
It’s morale.

33:08.55
Lindsay
Yeah.

33:09.11
Stephen Halasnik
Yeah. So that’s why leadership is so important at schools because, you know, that’s, the the role of a leader, you know, to address that topic.

33:19.00
Lindsay
yeah

33:20.71
Stephen Halasnik
So it’s tough. I completely get that this is a challenging time. Well, it was a great podcast today. I really enjoyed my conversation with Lindsay Whorton from the Holdsworth Center for coming on today’s podcast. And, you know, also, you can also pick up her book, A New School Leadership Architecture. If you’d like, and if you are interested in learning more about a line of credit for organization, please also visit our website at nonprofitmbapodcast.com. Lindsay, ah if anyone wants to reach out to you, well how would they go about doing that?

34:00.41
Lindsay
The best way to find us, if if you search the Holdsworth Center, it’ll take you to our website. We’re on most social media channels. You can find me um on LinkedIn.

34:11.58
Lindsay
um So any of those routes will get you to us.

34:15.67
Stephen Halasnik
Great. Thanks for coming on today.

34:17.46
Lindsay
Yeah, thanks so much.

34:19.16
Stephen Halasnik
So, um you know, the taping of this is is the middle of the summer. um And I just want to remind, I want to thank for our listeners for trying to make this world a better place. I know Lindsay and i are doing it in our own special way, but you guys are out there in the front line on a constant basis and we need you.

34:41.46
Stephen Halasnik
You know, we need to, This is ah ah a tough environment to make the world a better place and we need you to be at your best. So I just want to remind you, just remember that you’re no good to your cause, your employees, your family, nor yourself if you aren’t taking good care of yourself first. Um, because, you know, solving these world problems is a marathon and not a sprint. And if you’re burnt out, then you’re not going to be very effective.

35:09.14
Stephen Halasnik
So whatever you need to do on a daily basis, think of yourself, whether that be exercising, meditating, praying, meeting a friend for a cup of coffee, whatever it is, make sure you’re thinking yourself first, because we, we know there’s a lot of unselfish people in this business who are really trying to do great things. Other than that, I want to thank you for listening to the Nonprofit MBA Podcast. and everybody have a fantastic day. I’ll see you later.