June 28, 2026

Episode 285: The Future of School Leadership with Debra Wilson

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What does effective school leadership look like in a rapidly changing world?

In this episode of Leaning Into Leadership, Darrin Peppard sits down with Debra Wilson, President of the National Association of Independent Schools (NAIS), for a thoughtful conversation about leadership, organizational alignment, AI, demographic shifts, and the future of education.

Drawing on more than two decades of experience supporting school leaders, Debra shares why today's educational challenges require leaders to move beyond the traditional "hero leader" model and embrace the power of strong leadership teams.

Together, Darrin and Debra explore how schools can adapt to changing family expectations, navigate increasing complexity, and create meaningful educational experiences that prepare students for an uncertain future.

In This Episode

  • Debra's journey from attorney to education leader
  • The evolution of school leadership over the past 25 years
  • Why leadership teams have become more important than ever
  • The role of alignment in successful schools and organizations
  • How demographic shifts are impacting education
  • What leaders should be considering about AI and the future of learning
  • The importance of creating meaningful educational experiences
  • Why today's students need schools to think differently
  • A powerful leadership lesson about seeking perspective and support
  • How leaders can build systems that create long-term success

Key Takeaway

"Nobody leads by themselves."

As schools become increasingly complex, leaders who build aligned teams, seek diverse perspectives, and focus on creating intentional experiences for students and families will be best positioned to thrive.

About Debra Wilson

Debra P. Wilson serves as President of the National Association of Independent Schools (NAIS). Prior to becoming president in 2023, she served as President of the Southern Association of Independent Schools (SAIS) and spent nearly two decades at NAIS as General Counsel, leading advocacy efforts, supporting schools through crises, and advancing best practices in governance and leadership.

Connect with Debra Wilson

LinkedIn:

https://www.linkedin.com/in/debrapwilson/

National Association of Independent Schools:

https://www.nais.org/

NAIS LinkedIn:

https://www.linkedin.com/company/nais/

New View EDU Podcast:

https://www.nais.org/resource-center/nais-podcasts/new-view-edu

Connect with Darrin Peppard

Website:

https://roadtoawesome.net

LinkedIn:

https://www.linkedin.com/in/darrinmpeppard

Learn more about coaching, consulting, keynote speaking, and leadership development opportunities through Road to Awesome.

Sponsor Spotlight:

This episode is sponsored by HeyTutor.

HeyTutor partners with schools and districts nationwide to provide evidence-based high-dosage tutoring support in Math and ELA while helping schools remain intentional about staff capacity and student support systems.

Learn more here: HeyTutor.com

Darrin (00:00)

All right, my friends, welcome into the Leaning Into Leadership podcast. This is episode 285. One of the biggest mistakes that leaders make is believing that they have to carry everything themselves. And maybe this is because leadership has traditionally been portrayed as a solo act. You know, the principal who has all the answers, or the superintendent that makes every decision, or even the head of school who's trying to carry the entire organization on their shoulders.

The reality is this, schools have become far too complex for any one leader to hold it all together all by themselves. The strongest schools today aren't led by superheroes, they're led by aligned leadership teams.

My guest today, Deborah Wilson, the president of the National Association of Independent Schools, joins me for a conversation about leadership, alignment, the future of education, the impact of AI, changing family expectations, and why collaboration has become one of the most important leadership skills of our time. Now, before we jump in, I want to thank our sponsor for today's episode, Hey Tutor. Heytutor is more than just a tutoring provider. They are a true partner for districts committed to improving student outcomes. As a recipient of the National Student Support Accelerator Badge for High Quality Tutoring, Hey Tutor delivers targeted support in both math and language arts that help schools close the learning gaps and strengthen student achievement.

As leaders, we're constantly looking for ways to create better opportunities for students while supporting our teachers and our staff. HeyTutor helps districts do exactly that through high-impact tutoring programs designed to produce measurable results. My favorite thing about Hay Tutor is they do all of the personnel work for you.

They recruit, they hire, they train, and they supervise the tutors, which means for your already overtaxed leadership team, that's one less thing that has to be on their plate. To learn more about how Heytutor can help you and support your schools, visit them at heytutor.com, or even better, go down, hit the link in the show notes because that'll let them know you heard about them here on the Leaning Into Leadership podcast.

Now, if you've ever wondered what the future of school leadership looks like or how leadership teams can better navigate the challenges ahead, this conversation with Deborah Wilson is for you. I'll see you on the other side.

Darrin Peppard (00:00)

All right, my friends, welcome into this episode of the Leaning Into Leadership podcast. My guest today, Deborah Wilson from the National Association of Independent Schools. Deborah, thank you so much for joining me here on the show.

Debra Wilson (00:13)

Darren, I'm just thrilled to be here. Thank you for having me.

Darrin Peppard (00:16)

Absolutely. So before we jump into our conversation, and I know given the conversations that you and I have already had, we're going to go really deep into kind of where we see education leadership now and where we see it going in the future. But before we chase after that, let's maybe give you a moment or two to orient our audience into who you are, what you do, and what you're all about.

Debra Wilson (00:38)

Absolutely. So I work for the National Association of Independent Schools. Independent schools are, they're sort of a piece of the private school universe. Private schools as a whole educate, somewhere between like 11.

say 10 and 11 and half percent. Independent schools are truly independent. They don't tend to be like parochial schools or tied to an outside institution. They are usually standalone entities. They're independent in program, in governance, and in financial structure, which means they're largely tuition-driven. Sometimes they have other sources of financial support too,

you know, generally speaking, they're tuition driven, they engage in fundraising, some of them have foundations, but they're truly independent schools. That's a phrase that's not very familiar in the education universe sometimes. When I first started working for NAIS the first time back in 2000, I didn't even know that I'd gone to an independent school. was unfamiliar with the phrase, but that is what we are. NAIS has about

2,000 members made up of independent schools and associations that support independent schools in different ways.

Darrin Peppard (01:56)

I think that's awesome. you know, you and I had this conversation before, but I'd like to maybe go, go back to that just a little bit. I know you are, if I remember correctly, you're you are an attorney by trade, not somebody who was there you go recovering attorney. I love that. That's that's I refer to myself as a recovering high school principal. So I completely understand where where you're coming from there.

Debra Wilson (02:09)

I'm a recovering attorney, Darren, yes.

Darrin Peppard (02:20)

Talk a little bit about how that background and maybe your own, like the personal side of your background led you in this direction. Because certainly, and I think sometimes I've talked about this here on the show before, people make the assumption that folks who are in education just always want it be an education. And that's just exactly what they wanted. But the truth is we all have our own unique path that gets us where they are or where we are. So maybe just talk a little bit about

that or maybe connect the threads on that.

Debra Wilson (02:50)

Yeah, you know, I, it's kind of interesting. When I was in college, I actually started off in college as an English physics double major. That was sort of hard to swing in the nineties. People didn't like you to double major too much. It was going to take a long time. So I ultimately graduated as an English major and I looked into teaching at that time. But interestingly, my dad,

really sort of discouraged me from going into teaching. He was really worried about where education was going. And I ultimately went to law school and, you know, at least back in the 90s, that's sort of one of the things that you did when you were keeping a lot of your options open. And also, I really like to help people. I mean, it's definitely sort of part and parcel of who I am to try to make things easier, better, you know, in the case of schools for school leaders.

But I loved law school. I absolutely, was one of my favorite times in education was going to law school. And right out of law school, I actually worked for the attorney general's honors program at the Department of Justice doing tax litigation. And I loved the people I worked with, some of the smartest people I've ever met, but I really didn't love what I was doing. What I really learned about myself was I need a sort of a broader purpose and really thinking about the impact that

that I could have, and particularly in the long run, sort of for the betterment of society, and again, like people, individual people. I'm from a pretty serious education family. My parents were both first generation to go to college. My grandparents had pretty limited education, and they worked in mills in Connecticut. So education's always been a huge part of my family and my family's story.

so when I was looking around, really thinking I wanted to leave DOJ, I, I saw a job listing for NAIS. They were actually looking for somebody to do regulatory work. And, I love that kind of work. It's sort of what drove me to, to working for the tax division at DOJ. And so I applied because I was like, well, this is not quite directly related to education, but this is something I understand and it's something I really like to do. And I can use my time.

to hopefully make things a little easier to understand for those who are really engaged in education day to day. So I joined NEIS in 2000 and I was so fortunate to work for people who really believed in...

letting me learn and grow through that job. I had a wonderful president, Pat Bassett, who really encouraged my growth, was a fabulous mentor to me. And over time I became general counsel of the association. And so in that capacity, I led all of sort of the white papers and research and things on behalf of schools and school issues, supporting the government relations group within the organization.

And then also doing and coordinating all the in-house legal work for NAIS, which I loved. NAIS is staffed with super thoughtful people who really believe in education and believe in our schools. And in 2019, I left to become the president of the Southern Association of Independent Schools, which unlike NAIS is an accrediting body, it accredits about 400 schools. And I loved my time there. I was there all through COVID. But then the president position at NAIS

opened up and so I applied and I began in August of 2023. So this coming August will be three years in this position, which has been a fascinating journey and just one that I've loved. it's a just, it's a guess you all know, it's a gift to work with schools, it's a gift to work with educators. They are just some of the most committed and hardworking people you will ever find. And really,

thinking about just the long-term benefit and the best interests of children. And it's challenging work, as I know you well know, but it's also, I think, some of the best and most purposeful work we can do.

Darrin Peppard (06:36)

Absolutely. Well, and I'm, you know, I will say I'm grateful you're in that role. Just, just getting to know you a little bit. think you're certainly the right person to be leading that organization. And let's, let's dig into that just a little bit more. So you said you're, you're essentially at that three year mark. So let's, let's reflect maybe a little bit on those three years specifically from a leadership lens, whether that's your leadership or the leadership of those individuals, those schools.

that are out there doing the work every day, what are some things that you have learned or that maybe stand out that leaders should be really focusing on and thinking about both now, but then also going forward?

Debra Wilson (07:18)

Yeah, we, NAS has a magazine, It has an independent school magazine. And so I was literally just writing this for an upcoming issue that we have on leadership and on Headship in particular. And, you know, I've been working with heads of school for a long time, for, you know, a little over 25 years now. And interestingly, at my school, I was like a friend of my head of school. I loved my head and I write about him pretty often. And Headship has

just changed so much. Like when I look back over the last 25 years, and I know you've seen the shift too, just what leaders can do by themselves is, you know, they can't hold the whole of the school in their head anymore the way that they used to. And so, you know, one of the things that I see heads working on is really their leadership team and the team dynamics. I think particularly as this next generation comes,

becomes more part of the leadership team as we see more millennials, we see more Gen Zers showing up in leadership teams and how they work in collaboration and teamwork. I think both schools have gotten too complex for heads to hold it all together in sort of that old school model. And it requires a lot more coordination with your team and really depth of skill in that sort of next layer of leadership. And I see heads working really hard to...

to get that right. They know that that's gonna be crucial to the success, their own success, but also the success of their schools and the wider team at every aspect. It's just, education's gotten a lot more complex in so many different ways. And so like that's the number one thing I think I see heads really working on. How do you think about your team? How do you build your team? How do you maintain it? And really...

coordinate across the school in ways that we haven't seen, I don't think, until the last, call it five or six years, I think probably starting a little bit before the pandemic and then carrying forward. Is that consistent with what you've seen? I know you've had a lot of conversations with leaders.

Darrin Peppard (09:15)

Man,

a hundred percent. it's honestly, that has been kind of the direction for me that my work has really started to shape and, you know, definitely supporting the individual leader, but the team aspect, you're right. You can't just carry the whole of the school or the whole of the organization in your brain anymore. And it can't simply be, and I think this is, this has been the interesting thing I've seen with, with leadership teams over the last handful of years.

It can't just simply be, well, here's the job description for this assistant. Here's the job description for this assistant. It's so much more that we as a collective team have to be aligned around this, this really clear goal. This really clear vision of where we believe we're going to go. Not the, not the mission and vision to go in the strategic plan. Those are important, but that just that clear, compelling vision of this is what we believe together is possible.

and each of us take on these specific parts of that, but we have to be able to support each other together. I love that you went to leadership teams because it is such an important element. And I think really, and I want you to react and run with this. I think really it is one of the biggest separators between schools and organizations that are having great success and those that just continue.

to follow Einstein's definition of insanity and it can just keep doing the same thing and expecting different results. But the reality is if your team isn't aligned and if your team's not doing that work where we're all together, just, okay, I said I was gonna let you react. I'm gonna stop talking and just let you run with that.

Debra Wilson (10:58)

No, but I think you're exactly right. We talk a lot internally about alignment. I we've been working really hard on that, but I think it's what a lot of schools are talking about too. And when you have that alignment, honestly, it's easier for people to go faster because they already know.

you know, they, what is it that the, a lot of our students say today, they understood the assignment, right? Like, you know, when you have that alignment, when you know where you're going, when you know, you know, at least roughly how you're gonna get there, I think it's hard in 2026 to know how you're gonna get anywhere, but you know, when you've got that kind of alignment, that sort of understanding, then it's so much easier to move forward more quickly. And honestly, as a leader, you can trust your team more. They can actually take on more because,

It makes everything just a little bit more predictable in terms of what people are doing and how they're thinking about the work. And it's hard, right? Because it's not as physically tangible. It's not like you're building a building or something. You're actually talking about the way people work and the way people fit together. when you're particularly...

You know, this time of year, know some schools are still in the hiring cycle. They're looking forward to next year. Maybe they're learning about some employees who are letting them know a little later they won't be coming back for next year. You know, hiring, when you've got great alignment and you've spent a lot of time sort of curating your culture, hiring becomes that much more important because you're really thinking about how is this person going to pick up the baton that the person leaving is going to hand to them and how do we get them in alignment in our school? And I think that's...

It is just so much of what's happening out there and what can really make a good school great and give them a lot of strategic impulsion to move forward.

Darrin Peppard (12:47)

Yeah, that is extremely well said. I think when leaders and I'm going to pause for just a second and say this, if you're listening right now and you maybe just landed your first principal job, or maybe you just finished your first year as a principal, just rewind the last seven minutes and just listen to it again, because it's that important. And then when you come back to the spot, hear this.

you have to invest the time in aligning your team. It isn't just about, here's a checklist of responsibilities. You you do discipline for A through L and you oversee the counselors and it's so much more than that. And when your team truly is aligned around, here's where we're going, gosh, just, there's a reason that I do that work all summer long with leadership teams all over the country because man, when you do it, whoo.

Holy cow, it's amazing what can happen on the back end. that, that's a super powerful takeaway right there. What are some things maybe that in addition to that, I mean, that's again, that's super powerful and super deep. Let's see if maybe there's one other thing we can dig into that over the last few years, or maybe I know you guys just recently had your national conference. Maybe it's a theme that was coming from there.

outside of the leadership team piece. Let's go further with some leadership stuff.

Debra Wilson (14:07)

Yeah.

I think, so there's two other things that I hear, well, there's a lot of things I hear leaders talk about, but there are two things that I know are very forefront. And, you know, one of them, there's been a ton of articles about lately in part because it's hitting higher education harder now. And it's, you know, this demographic cliff and just looking at, you know, as we have fewer students to educate, you know, and in our space, you know, call it K through 12 or pre-K through 12.

You know, how does the model of our schools hold up or where does it need to be tweaked or adjusted? Because this is hitting across the board right now, right? Like it's public schools, it's all private schools. You know, you've got between the demographic cliff and all these different models of education popping up, whether it's, you know, micro schools or home schools or, you know, charter schools, magnet schools. Like there are just so many different choices now and there are fewer students. So.

I think it's requiring of heads. And I know from our previous conversations that principals are thinking about this too. You know, I think school leaders have always thought about and worked hard to understand their, like the business model of the school, which we don't talk about necessarily a ton in day-to-day work and education, but you know, particularly if you have a huge physical plant and either through families moving plus, you know, families having fewer kids, you're seeing,

you know, just fewer students. If you look at the future demographics, those students are probably not coming back. So just that idea of, like how are we shifting to meet the needs of this current student body, but also looking at those numbers and what is that model? And then it's sort of, it's related because it's the AI conversation too, right? Like, so how does AI help? But also like, where could it potentially hurt students?

and what is that like future of being human? So what does the future look like for our students? I mean, I think AI, there's so much promise there and there are a lot of things that a lot of us worry about, particularly because we see the impacts of say social media and phones on the students in our schools and wonder, okay, like what things does AI kind of, you know, potentially have hidden that might not be so great for our students? So.

You know, there's a lot to unpack there, but I do think just understanding that business model of schools and where it's going with these shifting demographics. And then how can AI help us manage that problem, but also like what is AI looking like in our schools and how should we really be thinking about?

Darrin Peppard (16:31)

Yeah, absolutely. And I want to take both of those and kind of work backwards and thread them together. Certainly the AI conversation is something I hear from principals quite frequently, you know, that they're just, you know, kind of concerned. How do you find that balance? You know, some lean really heavily into, you know, leveraging AI as a tool, but, you know, certainly we want to, you know, teach our students that it's more than just, you know, Hey, crank out an essay on Macbeth for me and turn that in. But.

I think it goes back to the piece you said before that really thinking about how we do business now compared to how we did business five years ago, 10 years ago, whatever, we're certainly in a political climate right now around education, not just on the public side, but also on the private and independent side.

where we need to be listening to what is actually being told to us through legislative action, through parents taking their kids somewhere else, through the incredible growth of micro schools, online schools. How do we start to re-envision and not be so reactive to all these different

things that are occurring. You know, I'm certain that you have talked about it with your team. I talk about it with people all the time. We have to focus on what we can control and all these other external pressures. We don't have any control of those, but if we're not willing to, I guess, for want of a better phrase, look in the mirror and say, are we really producing? Are we really doing what our current clientele and our future clientele really need?

certainly the AI piece just ties so tightly in with that. It's almost just one symptom of the entire process. So let's maybe go here with that. What are some things that, whether it's NAIS or maybe it's some of the different building heads that you work with or have gotten to know, what are some things you're seeing or talking about in this particular, you know,

that we've got to start doing school differently.

Debra Wilson (18:50)

Yeah, I love the way you put that. think the...

Part of it is really understanding that our students and our families, they're having an educational experience, right? It's not just what happens in pre-calculus or it's not just what happens in French class. It's everything that happens from, I don't know, even the notification they get from power school or Canvas in the morning to carpool to...

you know, lunch, like it's literally the whole.

experience of education. there's actually there's an interesting article about this and it focused on higher education. It might have been in the New Yorker. But it was actually talking about higher education and how people are choosing different kinds of college experiences. Like there's been this huge interest, growing interest in, you know, large state schools with football teams and like the whole, you know, kind of like straight out of the view book of, you know, and students saying, no, I really want that experience. And I think we

have to really be thinking about that in K-12 because you know what we see I think with so much movement between different kinds of schools and different sorts of educational options popping up is is that drive for I want a different kind of experience and you can't be everything to everybody so when you think about your school it's like okay what does that experience look like you know I think you know we've seen huge growth in Montessori schools particularly Montessori charter schools I mean that wasn't that didn't even exist 25 years ago right

or they were just starting to exist maybe 25 years ago. But it's a particular push for families that are looking for that kind of experience. so, you know, and I think this can be really hard for leaders, especially of larger schools, because doing these kinds of things to scale, know, some high schools, the public high school near me, they graduate over a thousand kids a year.

thinking about that experience at that scale and understanding, and exactly as you say, listening, but you can listen, you hear a lot of different things that people are seeking out or want.

At the core, what I hear a lot of leaders talk about, you every parent wants to make sure you know their child, that their child is known in your school. So I hear a lot of leaders talking about that. And, you know, and they're sort of staffing and thinking about things differently. Like we know that students, student mental health pre-pandemic was not great. And post-pandemic, it really hasn't gotten any better. So how do we think about student support holistically, right?

So your counseling program, your sports program, the teachers are aware, like how are you coordinating that? So it's not that you have one person in a school aware of what a child is struggling with, but every other adult who's encountering that child doesn't understand what's happening, right? So how do we coordinate? And it kind of gets back to what we were talking about with the leadership teams, right? Like it's not just the leadership team at the top. How do you coordinate student support in your school?

you know, really what does that look like? And from a parent perspective, you know, we know parent anxiety and loneliness is higher than it's probably ever been. The Surgeon General put that report out a few years ago. How are we communicating with families so that they understand that we know what they're going through? And I think this is, it's a little bit of a pivot. You know, when you and I were in school, our parents either dropped us off or just sent us on our way on our bikes and

They, I'm not sure my parents actually thought about me a whole lot again during the day. mean, you know, they loved me and cared for me, but they definitely didn't think about me as much during their working day as I think about my kids. Right. So, you know, I think that's like, so what's the current student experience? And then to your point, what are these students going to need in the future? So when we look at AI, and I think this is the really hard part, right? Because you're projecting forward to something we really can't see. And.

Darrin Peppard (22:20)

Right.

Debra Wilson (22:39)

parents tend to be more comfortable in an education environment that looks like the one they experienced. So, you know, we're listening, we're trying to meet the current needs, we're looking at the current student experience, but then we're having to project forward to a type of education potentially that doesn't...

necessarily look like what the education of all students has looked like for the last, I know, call it 100 years, right? And so, like, how do you listen and evolve at the same time? And particularly when everybody's anxiety is up really high about their future of their own children. If you have tapped that, like, let me know because, you know, I see school leaders working on those issues every day.

Darrin Peppard (23:23)

Well, and I think I mean you said that so very very well I think a lot of why we see all these other options Coming is that exact reason that you know? typically, especially your like you mentioned your your you know neighborhood high school that graduates the thousand kids a year they are Serving all they're having that you know that grand experience that that you talked about but

When you couple in, now before I even say that, I'm gonna say this. There have always been kids that didn't fit in well or feel like this is my, you know, the experience I want in the traditional large, you know, US high school. I led a high school of almost 1500 students. We had kids that they didn't just plug in well there.

Luckily, our alternative school, a school of about 100 kids had a whole different type of experience for them. But anyway, I think that's a lot of why we're seeing more and more of those different options start to come up. But it is very much juxtaposed against parents who this is what I remember. This is what school should look like. And we're getting some of that starting to come back that, you know, maybe, especially with public schools that are trying to make a

make this transition, the more traditional thinking it's like, whoa, whoa, whoa, rain that back in. That's not, you you're stepping outside of your lane. I think it's a huge challenge for leaders. And I, wish I had an incredible answer to say, if you just do this. But the reality is now if you're leading a small school, if you're leading a micro school, you can lean into it very much in almost an entrepreneurial way of

Here specifically is the problem we solve or the niche that we fit. And then those who that's what they're looking for are going to find you when you're in a larger, more traditional school, whether that's on the public side or the private side. You're serving a lot of different needs, right? Yeah, a hundred percent. Differentiation is the actually the perfect word for that. And it's, it's a challenge.

Debra Wilson (25:13)

Right.

Differentiating is hard, right? Yeah.

Yeah.

Yeah, particularly within that larger body, like the local public high school near me actually does a fabulous job. In some ways they've reached such scale that they can do really interesting things. I mean, it's more or less a small college, right? So they can do like little sub groups, but even that you're still doing it with, you know, 4,000 teenagers without fully formed prefrontal cortexes. And you've got to, you know,

Coordinate the whole thing, you know, we we talk about the adults a lot in leadership and leadership teams and things but then you know we've got the sort of random factor of the of the students in the mix and and That kind of differentiation still requires a lot of adults in the mix So in a time, I think when people are looking at budget constraints And you know, I just picked up a new book that tells me that constraints are not a bad thing I think it's called like inside the box or something like that But when you're looking at budget constraints

You can't differentiate by just keep adding more and more staff, particularly if your student numbers are going down. So, you know, we're at a fascinating point that, you I think a lot of leaders are wrestling with these problems, but particularly recognizing that our students' futures are probably going to be so much different than what any of us experienced. And how do we think about the knowledge, skills, and traits that they're going to need to navigate that time successfully?

You know, there's, we are not lacking for issues to tackle in education right now. I'll just, I'll put it there. I mean, it's exciting stuff, right? Like I, and I know you have these conversations. know, one of the things I told you that I love about your podcast is you come at leadership from such a positive direction. And I think it's easy to feel weighed down by these things, but they're also like some of the most exciting things that we can be thinking and talking about.

Darrin Peppard (26:52)

Yeah.

Yeah.

Yeah, for sure. Man, this is such a great conversation. We're at that point, I normally would say, okay, I'm gonna ask you the last question to ask everybody, but I wanna ask one more before I do that. And this may take us down another rabbit hole, I don't know. But what might be one piece of advice that you would share with school leaders, especially those who are fairly new in the role?

What might be one thing you would tell them to be thinking about or to go and do that would really have impact both on their own leadership, but more importantly on those that they lead?

Debra Wilson (27:50)

Yes, so there's one thing that I figured out a few years ago that I lean into all the time. And I tell new leaders this. If something is spinning in your head too much, too long, it's keeping you up at night and not, you know, sort of an existential crisis kind of, but like, you know, there's just something you're trying to figure out and you're having a really hard time doing that. It means that you don't, you either don't know enough or you don't have the

right number of minds or the right numbers of perspective to help you navigate whatever that thing is. When that happens, you can't sit on that. You need to reach out to those who can actually help you figure it out. For those of us who are in the Gen X category, we're used to figuring things out. Darren, I don't know about you. I would lose my house key on a regular basis. I had to get the garbage can out of the garbage can thing and I'd climb through the window into the garage and like...

You know, you just figured things out, right?

You can't really do that as a leader. I think what's, there's a great book Jenny Wallace just wrote on mattering and she did the one before that. It was more kind of about mattering in education.

You have to recognize that there's a certain humility to, you know, asking other people for help or asking them for their insights or helping you to think through things. But people want to do that. And people in education, I think, want to do that more than almost any other thing, you know, other than maybe medicine, right? Like when we reach out to other educators and say, can you help me figure this out? It is helping you figure it out, but it is also helping them because

It's a recognition of their expertise and what they can bring to the table. And you should never sort of burden yourself with not being open to those things. Like these are resources and peers who can just help you move things forward in ways that you might not be thinking about. And I think we all just spend too much time in our heads spinning by ourselves when we really can reach out to others to help us think it through.

You might not take everybody's perspective, but it will help you get to a more well-rounded outcome and it will sort of calm your leadership brain down. So, you know, and I think as a leader, like you go in and you kind of feel like, you know, I am a leader, like, and I now need to lead. Nobody leads by themselves. In fact, if you lead by yourself, my mentor Pat used to say, if you look, if you, if you get too far out in front, you start to look like the enemy, right? So you need to bring people along anyway.

So building consensus is important as a leader, but just bringing in those outside voices, I think I would have saved myself a lot of sleepless nights if I'd done some of that earlier.

Darrin Peppard (30:28)

I would agree with you a hundred percent on that. Both a fantastic, fantastic statement there, but also yes, as the leader who the first couple of years in my principalship thought I had to be the superhero to everyone, I absolutely could have saved myself a lot of pain and heartache and sleepless nights had I understood that put away the cape, open up your ears and ask a lot of questions.

best thing you can do as a leader. So I love that very much. I'm so glad to ask that question. So now I will ask you the last question that I ask everybody here on the show. So, Debra, you're on the Leaning Into Leadership podcast. So tell us how you're leaning into leadership right now.

Debra Wilson (31:08)

Yeah, you know, so I mean, we've had a wild three years. We did a rebranding exercise. We launched a new website. We just finished a strategic plan. My team hasn't voted me off the island yet, which is a good sign. And now it's about like stabilizing systems, right? We've been doing a lot of work on culture and how we work together and how we think about it. And now we're looking at this new strategic plan and thinking about like, not just how

not just what are we moving forward, but really how are we moving it forward? Like what are, we're a fairly virtual organization. Like what are the tools, what are the platforms? Like how do we get alignment, but then how do we have systems in place to help us do these things so that we can all see the progress that we're making? We don't overly hamper people with like too much process.

but we give ourselves like the structure and the consistency so that we can do it well. Moving fast is a lot of fun. And I think like where I'm leaning in, it's one of the harder things about leadership for me, Darren, but I've gotten, think, a little better about it over time. And it's going slow to go fast, right? So what are those foundational things that we're building now that are gonna help us?

really be able to accelerate into the future. We have plenty going on. We have a lot of really cool initiatives and things that I'm really excited about. But that piece, you can't forget those foundational pieces at this point, because that's what's gonna help support you really executing well on things. And particularly when you have a lot of moving pieces, you need those execution aids in some ways, right, to help move it forward.

And so that's really where I'm leaning into leadership right now. And it's kind of fun. Like I've done a little bit of this before. And so it's hard, but I also know the payoff on it that comes is exciting. And I work with a fabulous team of people. Like the whole staff is incredible. So I am excited to see what we can do.

Darrin Peppard (33:12)

Absolutely. I love that answer. That's super fantastic. So certainly Deborah, people are going to, you know, want to follow the organization, want to follow you, you know, plug in and just continue learning from you. So what are some ways that people can get in touch with you?

Debra Wilson (33:27)

So I'm on LinkedIn. You can find me pretty easily. I think it'll be in your show notes. And it's just Debra B. Wilson at NEIS and the website's neis.org. And we also have a podcast, New View EDU, where we talk about, you know, kind of what's on the forefront of education and leaders minds. So yeah, and I look forward to it. you know, we're, we're, we are all in the education boat together. So I'm always happy to, to be a support.

Darrin Peppard (33:54)

Yes, we will make sure all of that stuff is down in the show notes so you can get in touch with Deborah. Man, this has been so wonderful. I'm so glad we had the opportunity to have this conversation. Thank you, Deborah, for joining me here on Leaning Into Leadership.

Debra Wilson (34:07)

Thank you so much, Darren. It's been a pleasure.

All right, folks, awesome conversation there with Deborah Wilson. I really appreciate her coming and joining me here on the show. We had such a wonderful time visiting, both on camera and of course after we stopped the recording. She's fantastic. Make sure you get down there in the show notes and click on those links. Get yourself connected with Deborah Wilson. And now it's time for a pep talk.

So this week on the Pep Talk, I just want to lean right into something that Deborah said. In fact, it was so good that I'm going to directly quote her. She said, if something is spinning in your head too much and keeping you up at night, you either don't know enough yet or you don't have enough perspectives helping you solve it. So this whole episode was about not being the leader out there trying to do everything, not being the superhero, not being the person that does it alone.

And that quote to me just summarizes the importance of not flying solo. Look, many of you who are listening are getting ready to start a new leadership role. Maybe for some of you it's the first time you had the opportunity to be the principal, the assistant principal, the superintendent. Don't try to do it on your own. Make sure that you are building a team around you. Make sure you're listening to different perspectives because that's important. That's how you get

All your things taken care of, and you get the problem solved, not simply by you doing it alone. Hey, that's what I've got for you this week, folks. As always, thanks so much for listening here to the Leaning Into Leadership Podcast. Please rate, review, and subscribe. Make sure you're sharing this with other people who might enjoy leaning into leadership as well. Get out there, have a road-to-awesome week.