The Failure Gap

speaker-0 (00:00.576)
Welcome to the Failure Gap, the podcast where leaders get real about what it takes to move from agreement to alignment and turn strategy into action. I'm Julie Williamson, CEO of Karrikins Group and author of the best-selling book Make How Matter. I started this podcast because I've seen the same pattern in boardrooms, leadership teams, and organizations of every size. Smart people agree on the strategy, the priorities, and the goals, but progress still stalls.

The space between knowing what to do and aligning your team around how to do it together is what I call the failure gap. At Karrikins Group, our work is focused on helping leaders close the failure gap by making how matter. So alignment becomes more than agreement in the room. It becomes shared action across the organization. In each episode, I sit down with leaders from all sorts of organizations.

To talk about the real stories behind transformation, the tough lessons, the hard decisions, and the breakthroughs that helped them to move forward. Thank you for joining me today. Now let's close the failure gap. We love talking with interesting people, and today we're joined by Debra Wilson. She's the president of the National Association of Independent Schools. And I know I'm really looking forward to this conversation because as the president of

an organization that's working to help nonprofits to really show up in their own world and their own spaces as well as possible. I think the strategic direction for all of that is going to be so challenging as we go forward. So looking forward to the conversation. And Debra, welcome to the Failure Gap.

speaker-1 (01:42.112)
Julie, it is so nice to be here. Thank you for having me.

speaker-0 (01:45.388)
Such a pleasure. I would love it if you would take a few minutes and just give our listeners some thoughts about the twists and turns that have landed you into this role as president of NAIS, because I'm sure it's been quite the adventure. Yeah.

speaker-1 (02:00.036)
well, you know, education is not boring. So but even even before that, I little did I know, I went to a small independent school in Connecticut, on Connecticut College campus. I went to the Williams School and I didn't even know it was an independent school. Independent schools, they tend to be independently governed, they set their own mission, vision, values, they

create their own programs, you know, limited by, you know, whatever state structure they're functioning in. And and they're they tend to be independently financed. They have tuitions, they're independently governed, they have independent boards. but sure enough, like I went to an independent school and until 2000 when I applied to join NEIS, I didn't even know what an independent school was, honestly. when I was growing up there were private schools and there were public schools. And Williams, as far as our

whole family was concerned was a private school. we were my siblings and I were the first generation to go to a private school in our family. My parents, their well, my grandparents all all worked in mills and restaurants growing up in Connecticut. And so my parents were the first generation to go to college. and and so they chose Williams for us because, you know, it was a

We had a pretty big high school near us and a pretty big junior high. We didn't have middle schools back then. We had junior highs and and they really were looking for like a smaller atmosphere for us and a more challenging academic. So we went to Williams and I went through college and and took a couple of years and then I went to law school, which I loved. And right out of law school I was working for the Department of Justice in the tax division.

And I did that long enough to realize like I could do that, but it wasn't like it wasn't exciting to me. Like I'm I'm sort of a I'm a very much a purpose driven person. And so like I love the people I worked with. The work was really interesting, but it just wasn't I don't know, it wasn't filling my cup. And so I kind of did a self intervention and I said, Okay, well, what am I most interested in? like what

speaker-1 (04:09.238)
what what might fill my cup? Like what's important to me? And education was definitely one of those things. I'm from a big education family, big believers in education. And NEIS was looking for somebody to do regulatory work. And so I applied and I love the people that I met. And it was so funny, my then boyfriend now husband was like, this might be the only time that having gone to, you know, an independent school like is getting you this job.

Because, you know, they were like, well, you went to an independent school. And I said, well, you know, who knew? and so I started doing that. I was the first lawyer the association had ever hired. I got to know a lot of the lawyers who were supporting the organization. And I started, so I was doing the regulatory work. I was working with the government relations team. And then I started doing just a lot of writing around legal issues that schools run into all the time. And I was

Coordinating all work with outside attorneys and doing more and more things internally, building systems and really building a network and mentors to help me learn how to build those systems and think through these things. And, you know, over time I became staff attorney general counsel and I was at NEIS for almost 20 years. So I, and I got into a lot of work around governance. You know, a lot of legal issues can come up in the governance,

space and helping schools really think about risk management, you know, and risks writ large, not just the legal compliance pieces, but you know, the things that can impact how the organization, you know, is going to keep going. You know, what does stewardship look like? What are the risks? What are the opportunities? All those kinds of things. And I did a lot of work around student health and wellness. and

Helping schools sort of think about the overall ecosystem that we create for schools or in schools for the student experience. And I loved it. And I did it for a long time. And then the presidency of the Southern Association of Independent Schools opened up. And at that point, I loved what I was doing. I wasn't quite tired of the legal stuff, but so many other interests were being fed by how like broad my portfolio was getting.

speaker-1 (06:28.402)
And so I applied and took that job and I was there through the pandemic. and SAS is an accrediting body, so I got some exposure to accreditation too. NAS is a membership organization, so we don't do accreditation. And I loved it. And it it sort of let me lean in a little bit more on the leadership front. I was when I was at NAS before I left, I was a member of the management team. You know, I definitely had that.

leadership seat at the table, but it was it was exciting to kind of have my first presidency and to get to do that. And really during the pandemic in education, you know, that's a that's a time nobody in education will ever forget anytime soon. So and and then my my friend and predecessor Donna Orham was retiring. And so this position opened up and I applied and it just it some seemed like the right time to to come back and take what I'd learned at SAIS and

apply it in NAIS, which is a it's a much bigger organization. SAIS when I was there had I think we were eight or nine staff members total, which is very fun. It's like it's nimble to have a small team. You can get a lot done. Communication is so much easier because everybody's together, like it's easier to pull people together. At NAIS we have over fifty staff members. We're largely virtual organizations, so we're pretty spread out, which has its own challenges. SAIS is also virtual.

But it's been it's been fun to be back. And so I just completed my third year at the association, just this month in August.

speaker-0 (08:02.606)
Well, congratulations on that. And it sounds like quite the journey. I love that you did a self-intervention. And I just want our listeners to take that away from your experience that it is possible to take a step back and intervene on yourself around whether you are doing something that fills your cup.

speaker-1 (08:19.842)
Yep, well, and like it's important. I mean, I know you you have this great saying which I adore. you know, there is no wrong step, there's just the next step. But sometimes when you feel like the path you're going down, I don't know, it's like when you're hiking and things seem really overgrown and you're like, I'm not so sure about this and it's okay to sort of take another side path that might look a little better. I'm a big fan of self interventions. I'm I'm

I I love talking with people when they're having a self intervention. It's like one of my favorite things because it's you have to be brave to do it, but it's often so worthwhile.

speaker-0 (08:52.846)
For sure. I think the the times when I've redirected have been the most productive and scary and challenging sometimes too, but also ultimately really re rewarding. Yeah. Well, thank you for sharing that. And I appreciate it. Let's pivot a little bit and start talking about the failure gap because you see this, I think, come up in a couple of different ways in your role. One is as the president of an organization that has a strategy that you're working to deliver, and it's so easy to think.

speaker-1 (09:02.808)
Yeah. Yeah.

speaker-0 (09:21.834)
agree that a strategy is a good idea and to struggle to then get everyone aligned and implementing on it together. Also as someone who works with members to help them with things like board alignment and how do we make sure that the board is in service to the goals of the organization and vice versa. What does that look like? I think there's a lot of opportunity there to talk about the failure gap and probably other parts of your world as you look at the bigger education environment.

and what's happening and how you want to influence or impact it. There's probably a lot of agreement around what needs to happen and challenges at a macro level aligning and and getting around it, especially as I think about things like AI and other digital impacts that are having that are changing education in really significant ways. So I think we have a few different threads we can pull.

speaker-1 (10:13.324)
Yeah. Let's jump

speaker-0 (10:15.146)
Let's jump in. Let's do it. Why don't we start with your role as the president of this organization? And I know that you and your team are working on implementing a new strategy. And again, we see this all the time in business that strategy looks great on paper. You put a lot of time and energy into it. Everybody feels really good about it. And there's a lot of agreement that it's a good idea. And then we get into implementation and alignment can become a struggle because we've got day jobs, right? That we have to do.

Tell me a little bit about how you're working with your team to make sure that you bring your strategy to

speaker-1 (10:51.564)
Okay, so before I like even start talking about this, I'm gonna knock on wood because you know, we're in the we're in the process, right? We're doing this right now. we really for the first two years, we spent a lot of time building tools and capacity, common language, agreeing to some of the places where we didn't have alignment and figuring out, you know, a lot of the things that that you point out, like how do decisions get made? Like what framework are we using? How are we doing those things?

like other organizations, we're work in progress, but like we're we're building that commitment to, okay, when we want to launch a new thing, particularly a substantial thing, you know, we don't do this with everything. Like we really look at, okay, like budgetarily, what's it taking? What resources are it taking? What teams we work in teams in the organization? What teams is it impacting? Do they have the resources to help support this initiative? How does it align to we have our mission, vision and values?

You know, we also have pillars that when we did a lot of branding work, we know our schools are really looking to us for. So like we we really have worked hard on developing the tools to help create that alignment up front. So we spent a couple of years doing that and then we really got into strategic planning. and the strategic planning now, you know, doesn't look the way it did obviously fifteen years ago. You know, where you're like, Okay, these six things are the things we're gonna do and you just backwards design from those six things. As we all know, I don't know.

Who knows what AI is going to do in 18 months. So you have to be ready to pivot on. So we it's more like we have, you know, a few vectors of strategic direction. We feel good about those. But the process to even identify those, we engaged a lot with the membership. We got a ton of membership feedback. We we were working with an outside firm at a cognition, and we had interviews, we had surveys, we you name it, we did it. And

you know, kind of pulling everything together and everything, you know, we also knew from our marketing work that we had done and and knowing where we saw some things going across, you know, the sector or education writ large. But then the way we engage staff was a little bit different. And so staff has been was engaged from the beginning, but then we got into sort of smaller working groups doing sprints around okay, like what are some of these initiatives? What could this look like to make sure that we are building some staff understanding and alignment.

speaker-1 (13:14.06)
from the beginning, right? So and some of this was actually with the help of your book. I was, I was, you know, we had a lot of conversations about like how like because it comes down to, you know, are we using a shared language and a shared understanding to help create some of that alignment? So before we even had, you know, now we have like the fancy one page version of the plan. I think we have a five page version of the plan. Somewhere I think we have a 40 page version of the plan. But a lot of it comes down to like

What's our shared understanding of this?

speaker-0 (13:44.876)
I'm so glad the book has been a good resource for you. And one of the things that we emphasize there is the idea to talk, not tell. And it sounds like you're really doing that with your team as you work to create shared meaning around the strategy, not just when it's all done and on a one page poster, but through the process of creating it so that we always say, if you build it, they will come, but if you build it with them, they'll already be there.

And you're already that they're already there with you. Tell me a little bit about how you're working to create that shared meaning.

speaker-1 (14:16.31)
Yeah. you could not be more right. and that has certainly been our experience. I I do think most of us have received a strategic plan. So something's sort of being done to you, not with you. and so I'd I do hopefully we have reasonable clarity, reasonable understanding, and also just reasonable buy-in. because where we are now, you know, particularly this year, I mean, there are initiatives that, you know, we're we're starting, we're rolling out.

some of them are like they're multi year, particularly the technological ones. but we have to make some trade-offs like everybody does. And I do think, you know, where where alignment and agreement, you know, where you have agreement and then you don't have alignment is when people have to give up, you know, their favorite pet thing or the thing that they think is what gives them value in an organization. Right. And so when you have, I think, shared understanding

common meaning with some alignment. People see the hope of the future and they're not already feeling the loss of what they're not doing anymore. And they can start to see where they fit into this new vision of the future. I mean, change is hard. And I have to say, like as a leader, I have a bias towards action. So it's hard for me, you know, I I call it going slow to go fast. It's hard for me to take the time sometimes to do these things.

But it you know, in the end it it's such a big part of it. I mean, I I don't know if it's just my phase of life, but you know, for the longest time we've always said, you know, culture eat com eats competence for breakfast, right? And it's not until like you really like take that apart and you've seen it happen enough times or you've experienced it yourself that you you understand like a lot of what you're doing here and trying to create that buy buy in, trying to create that alignment is also too about shifting culture.

and about building culture along with vision. You know, if it's just like you're coming in and telling people what you see and what to do and things, you can be super competent at doing that. But if you're not bringing people along, that culture is going to eat you alive. so, you know, hope hopefully we're doing it well. You know, we we are a work in progress. There are going to be things that we look back and

speaker-1 (16:36.278)
and say, ooh, like that's something we should have done a little bit differently or taken our time with more or maybe moved a little faster on. But we've been very deliberate in just how we do that. We try, we're really trying to create that shared understanding and that shared buy-in.

speaker-0 (16:52.503)
I love that. And I think there's a time and a place to let action precede clarity, where you just have to take some steps and see what happens and then, you know, adjust from there. And there's a time to go slow to go fast and to take that time to bring people along and to make sure that they can understand the context for the hard choices that might create at least short term pain for them, but it creates a positive for the whole organization. And I think you're right.

That's where alignment fails.

speaker-1 (17:22.998)
Yeah. I mean, and you can phase that, right? Like, you know, we look at this year and we know this is like when a lot of things are double tracking, right? Some things will sunset and we also have to build up capacity in other and new areas that we haven't done before. And that's kind of scary itself. But these two things like kind of have to happen at the same time. And so you're asking a lot of your team when you're doing that. And so, you know, we brought in some additional support. happily we've really worked closely with the board to create alignment with them. So

to you know, to ask them for some extra funding to really to fund the foundations of these initiatives, you know, not not just the tech build out, but to say from an internal resource standpoint, you know, we're also going to need to build skills on staff. We're going to, you know, need additional outside support while we're doing this so that people aren't trying to do everything at the same time, because then nothing moves forward, right? Like if you just feel like somebody's just loading on more initiatives.

n nothing happens. so you have to kind of figure out how to do both at the same time and sustain it. I'm I'm a big sign cynic fan. I like a lot of things he's written. And so I think a lot about, you know, his pieces on tr trusting teams, like, you know, how do you create the circumstances for people to thrive? And I think having direct conversations about some of these things is incredibly helpful, but also to show staff that

You know, we're really trying to support and, you know, and and fund this like kind of crossover piece that we're doing here. You know, we're a nonprofit, so like it's not like we had tons of money just coming out of the woodwork, but you know, we're really trying to make it a sus sustainable shift to this sort of new strategic strategy.

speaker-0 (19:11.902)
I appreciate the precision with which you are sharing that perspective with your team because so often what I hear from people in times of transformation where this crossover moment hits, and it is a lot of work for everybody, is they'll say, our leaders, they have no idea what the impact of this is. And I talk to the leaders and they know exactly what the impact is. But they haven't connected, they haven't made that.

clear to their teams. Like I understand what I'm asking you to do is really hard. Yeah. And part of it in is because they don't want to be they don't want to acknowledge the hard. But their teams are experiencing it every day. You can't hide it from them.

speaker-1 (19:52.472)
Well well and you have to you know, when you're the when you're the president or CEO too, like you have to make sure that you're the people who report to you are cascading that down. Right. Like I would love to speak to everybody on my staff individually all the time and there's still only twenty four hours in a day. So, you know, to make sure that people n know that, you know, and like I said, we're working progress. So, you know, we we're working on that, but we do talk about it because change is hard.

I mean, we've all been through organizational change at one point in time or another. So to sort of recognize that I'm sure my team is tired of me talking about the messy middle. but you know, but to just to recognize like this is messy and it's, you know, ambiguous and it's uncomfortable. But but I think we've gotten some clarity through the strategic plan and you know, and we get a little more clarity day to day as we get deeper into these projects. So and and that part's exciting and you know.

Sometimes we talk a little bit too much about how hard change is and not enough. And like, you know, it's also exciting. Like this is fun, good stuff to be working on.

speaker-0 (20:58.988)
Yeah. I like to tell people too, you you get to choose your hard. You get to choose it's hard it's hard work to move towards the future and to do things differently, but it's also hard to stay stuck where you are and to become irrelevant. So choose which hard you want.

speaker-1 (21:12.856)
Yes.

Yeah. Yeah, that that that heart does not appeal to me. So like I'm I'm going I'm going to number one. Yeah.

speaker-0 (21:22.334)
Exactly. Right. I think most people would. But when you put it that way, sometimes they're like, okay, okay. So yeah, this is going to be hard, but it's a it's a better hard than the other choice. Yeah. Yeah. Well, you brought up boards as well. And I do want to talk a little bit about boards because I don't know about you, but I work with a lot of senior leaders and executive teams who have let's call it challenging relationships with their boards. And everybody agrees they want a great, healthy board that's dynamic and that's engaged and that's

helpful to the to the business or to the school, whatever it might be. And yet somehow it seems to be a struggle to get there and to get aligned in that way and to have a board that is aligned with the management team that they're working with, whether it's for a school or a business. And I I like to tell executives or senior leaders or heads of school, if you feel overwhelming anxiety at the thought of meeting with your board, something is not right. There's something is that's not a healthy dynamic to have.

So talk to us a little bit about your observation of what what does it take to get that alignment with the board so that you have a healthy and thriving relationship versus this more contentious or anxiety producing relationship that I think everybody agrees they don't want, but they don't know how to get out of.

speaker-1 (22:40.588)
Yeah. what I've noticed particularly in the last few few years too is boards can change on a dime. you know, you can talk to somebody, they could have a very healthy relationship with the board. The board could be in a really healthy place in September and then you talk to them again in March and one or two things have just sent stuff skidding sideways. I have sort of two initiatives on

One is NAIS. We have a big initiative. It's called the Leadership Alignment Project. And we received a million dollar gift last year for this project, which is fabulous. And we have an initial cohort of schools. And we're trying to get into that secret sauce of like what creates alignment. some of it we know is tools based. So how do you get the leadership of a board and the leadership, you know, the management of a school looking at the same data and understanding the same.

thing. And what are those points? So, you know, it's not just financial health. You know, some of it is looking at demographics, some of it is looking at succession planning. Like where is the school at any point in time? So we're working very closely with this cohort to build this out a little bit more. So that, you know, and it doesn't necessarily, you know, sometimes we mistake we we mistake that people like agree that they're looking at the same data. You know, it's nice niceness versus kindness, right?

So it's sort of like the way you talk about agreement and alignment, but some of it is like somebody doesn't want to hurt anybody's feelings until like you push them to the edge and then they come out with something you're like, wow, like why didn't she say that six months ago? Right. So like how do we help teams have these conversations that can be hard? And if you've never been trained to have them or you know, you're not regularly in a workplace, or you're not regularly managing teams or certainly not, you know, necessarily in education.

How how do we give boards where you have a good amount of turnover on a regular basis, and leadership teams where you can also have turnover? How do you give them sort of the the skills and the understanding to have consistent conversations so that they can stay in alignment, but are also having healthy conversations about stewarding, evolving, and the future of the school? So that's that project is like very

speaker-1 (25:04.406)
very focused on that because we know what happens when you have misalignment, you have a lot of leadership turnover. And in schools in the nonprofit world, that's where you lose a lot of momentum, you lose a lot of really good people, you can lose families. you know, parents, generally speaking, they want stability for their kids. They don't want a lot of drama. They don't want a lot of turnover. So, you know, the the health of that board leadership team dynamic.

is crucial to just the overall health of the school. So we're focusing on that internally. And then I've been involved in this sort of international international nonprofity looking piece on governance. And so it's looking at international schools and a bit on just general into independent schools here in the United States, but just thinking about like how do we make boards sort of learning ecosystems? How do we

introduce concepts around adult learning. So like there's basic good governance hygiene. And all boards need to have those things. You know, there have been a good number of studies on that. Boards should be doing self-evaluations. They should be evaluating their head of school or other CEO. Like there are those like baseline things and they shouldn't be deep in the operational weeds. But then, you know, how do you how do you bring a board along so that

they're learning about the ecosystem and particularly with schools, because it's complex. They're not widget factories. Or how do we bring them along to learn that too? Because some of at least in our industry, you know, I mean, education is its own sector. It has its own language. It has, you know, its own approach to like how do we think about things developmentally? I'd say probably 90 to 95% of the people on our boards have no education background other than their own personal experience.

So like how do you like how do you create sort of a shared glossary and just basic understanding of like what are we trying to do? How are we trying to do it? And and how can we help people who join boards really learn about the industry, not even so much from like benchmarks and dashboards, but understand like what are we trying to do in education? Because it's a it's a different kind of focal point.

speaker-1 (27:21.698)
So like that's like a it's a different kind of alignment. And you need all of like the corporate alignment and pieces like that, but then there's just a shared understanding about like what education is, and what is it in the concept of this fundamental school. So and it kind of it remains an age old question, but we know that it's getting farther and farther apart in education.

that I think is fueled by parent anxiety. You know, AI is not helping anyone's anxiety levels, but particularly if you're a parent and you have children, you know, your anxiety levels are higher than they've ever been since people started recording parental anxiety. So like when then when you bring that on a board, the temptation to be in the operational weeds is that much more complex. So like you've got, you know, you have to think about how do we educate people for that.

But and I know this is something you think a lot about, like how do we recruit for that? Like you almost never want to recruit somebody on your board who actually really wants to be on your board because they might have a misconstrued concept of what it means to serve on a board, and particularly in the nonprofit space where you're a steward for the future 20 years down the road. so we're spending some time with that too, and there are different times for different kinds of trustees to serve.

You know, when you're on a capital campaign is one kind of moment, when you're in strategic planning is another kind, when you're having, you know, a leadership transition is a different can be a different profile of a person on the board. So, you know, getting school leadership and board leadership to think more proactively about these things, I think can really help on the alignment front.

speaker-0 (28:59.404)
Yeah. I really appreciate too that you highlighted board education because I see that as a gap for a lot of boards that they just don't understand the business well enough, whether it's an independent school or, you know, a tech business, right? You need board members who actually know the industry and they don't have to be experts, but they have to understand how to put their experience within the context of whatever the the discipline happens to be in this case it's school. I do think I've certainly seen

Both parents and board members make the mistake of thinking that because they went to fourth grade, they know how to manage fourth grade.

speaker-1 (29:35.598)
Well and it changed a lot, right? And yeah. And and and you know, we also know, you know, when parents choose schools, a lot of times they're looking they're looking for their own experience in education, right? Like that's that's a comforting thing to say, you know, well this looks a lot like what I went through. But if you think about our kids' future, that may or may not actually

speaker-0 (30:01.752)
Right. Probably should not look like what you went through.

speaker-1 (30:04.59)
at least a chunk of it, right? Like, you know, it it's it's it's just very different. So I think understanding the business, but also understanding some of the philosophies, because sometimes w we just run into a culture gap and honestly a lot of our parents they're in for profit spaces. you know, they're and they're

speaker-0 (30:24.632)
A very different model.

speaker-1 (30:25.954)
Yeah, and they're lawyers or doctors or whatever, like they're they have just a completely different background. So when you start talking about sort of organizational philosophies and psychology, it's just not something they've had in their own personal experience. So and to be clear about exactly what are we looking for from board members.

speaker-0 (30:43.95)
No. You know, you also you talked it is your own role as a president of the organization and creating alignment early and often with your staff to your strategic plan. And it strikes me that you're also reflecting on the importance of leaders recognizing that board members need to be engaged early and often and that there is some repetition that's needed and you need to be engaging them in the conversation rather than

orienting towards the board as I see sometimes to use a school metaphor like going to the principal's office, right? Or asking for permission around things, but how instead do you orient towards them as partners in the joint effort of creating the best possible educational experience for your students and not see them as an adversary, but see them as a partner in that?

speaker-1 (31:37.058)
Yeah. Yeah. I mean I I think when I work with with when I work with my own board on that and when I work with school boards on that, it you know, people want to be useful. Like just, you know, how how we structure board meetings, you know, sit and get is not very compelling most of the time. Sometimes it's just unavoidable, you know. Particularly like, you know, our board meets

three times a year in person. We have a lot of committee meetings and things, but it's not it's not very often. We meet for a couple of days. So it's a longer period of time. But some of it is an element of like, we have to deep dive on some of this so that you understand the complexity or what we're investing in and that kind of thing. But but also to say like, okay, like what are we strategically, what are we using the board for? Like we want them to be strategic, but you can't just say like I can't just look at you and say, hey Julie, like

I want you to be strategic about education right now. Like, okay, like what do I do with that? Right. So, you know, how do you think about educating them for whatever the task is? How are you providing clarity around what you want from the board? Like, are you looking for a vote? Are you looking kind of for just a conversation and gut reaction, sort of a fishbowl type of conversation to inform your leadership thinking?

know, do you want some combination of that? Do you want to hear conversation and have a task force pick this up and come back to the board with a a solution or a couple of you know choices to make. You know, just being super clear about that. But if you think back to I mean pick your pick your like meetings that you felt most satisfied leaving, right? Usually you get to actually engage, you actually feel heard. You don't in my case, people don't necessarily need to agree with me, but like

the you know, having the chance to actually like talk it through, understand where people are coming from, and then understanding like the clear next steps and feeling, you know, that you've brought value to that conversation for the future of the organization, like those are big things we don't design for that a lot of times in board meetings. So that's part of kind of having that learning organization. So if you on a board to, you know, talk about what's happening in student wellness, which is a huge topic right now in education.

speaker-1 (34:00.278)
First you have to like s sort of share some background on like what are the trends writ large? What are people worried about? What do we know about our school? And then how do you, you know, create a strategic conversation that's not inviting them into middle school lunch, but is, you know, sort of talking about like, okay, like where do we want to be 10 years from now? And, you know, making sure the lines are clear, but that you're engaging them in the strategic conversation. They can't do that without education.

And they're not going to engage in that education unless you've created that learning culture to begin with. So like all these things work hand in hand. And and board members get excited. Like that's like a fun thing to do, right? You know, particularly in education, like it's such purposeful work and a lot of board members serve on boards because they believe it's important, because they know it's purposeful work, even if they don't know a whole lot about it. So it's actually easy to engage them when you think about it that way.

speaker-0 (34:59.81)
They're excited to be in service.

speaker-1 (35:01.866)
Exact well, exactly, right? Like everybody, you know, if you read Jenny Wallace's book on mattering, you know, being asked to participate in things like that, like you're excited to be in service, but you also feel like you matter when you get to provide service. there's like it's a it's a wonderful two-way street. And so we think about that a lot when we're thinking about working with boards.

speaker-0 (35:24.3)
Yeah. You know, I think about what you're talking about in terms of bringing the board along and having this education component and helping them to understand the bigger landscape, even though it's not their area of discipline or expertise. And I'm curious about what you are seeing or hearing from the schools that you work with about AI and this looming impact or change or area that they need to quickly

Come up to speed on, but also stay up to speed on because it's changing every day, month, week, right? It's like something different. how how do you see them navigating something that complex with their boards, which are only meeting, as you say, three times a year potentially, right? Or not getting together on a regular basis, so that they can stay ahead of what they need to know about and the decisions that need to be made now about.

speaker-1 (35:56.681)
Every minute.

speaker-0 (36:19.776)
a technology like AI in the educ in the world of education and specifically for their school and their students. What's what's happening there?

speaker-1 (36:29.228)
I there's so much happening there. Like even in like the period of time you just said all those things, I'm sure like 12 things have changed. Five new ed tech companies have popped up and six have closed. it you know, so at the I'll sort of I'll break it down in the buckets that I think about AI because it's such a it's got it's there's the now of AI and then there's the future of AI. Like where are our kids going? So the the biggest part and the one that I think is probably most relevant to

to board conversations in particular, are are really around like the existential questions. Like what is the purpose of education? What is the purpose of school? So, you know, for a long time school was mostly about knowledge. Like how are you gaining knowledge with a skills kind of component overlay, sort of nice to have? And this is, you know, I'm going back to like 50s, 60s, and then progressive education kind of came along and started really

doubling down into like what we call durable skills, like curiosity, creativity, all these pieces. Like as as we started to be able to measure those, we realized how important they were to the success of kids later, and to their engagement and happiness and all these other things. But and then like those those pieces kind of grew. So you you ended up with sort of knowledge, skills, and then in you know, kind of character.

And our schools live in that space. When we talk about our schools, we talk a lot about the student experience and the holistic student experience. So not just what happens in, you know, AP history, but what does happen in the middle school lunch room. Like what does that look like? What does that feel like? And how how are our schools together in community? AI really interrupts that to just start thinking about how important is knowledge exactly.

And what knowledge at what point? And we know AI, you know, it's like water damage. So your least engaged students have the best way of cheating, you know. So when you and I were in school, French class was my Achilles heel. I had a couple Achilles heel French class was definitely it. If I had an issue with my French assignment, I would call my friend Marion, or who was much better at French than I was, but still not.

speaker-1 (38:49.58)
particularly great. We could complain about French. We might share some bad answers. And then you just kind of buckle down and get through French. Me in 2026, I can go to Claude or some other tool that I don't even know exists and come up with all the answers to my French and learn. I will never ever do that perseverance of getting through French. That perseverance doesn't just help you with French. It helps you just learning how to persevere through doing hard things. So

There's like just this overall question of like what's the purpose of education? How are we thinking about it? A lot of my schools are talking about like emotional intelligence, like being in relationship. Like how how do we think about that? And does that does B.O. Human actually become more important in this time of AI? So like there's that big bubble question. And then you've got a little bit more of the day to day pieces. So how are teachers using AI when they're creating lesson plans? Are they using AI to grade student assignments? Like, how does that impact the student relationship?

That's getting a little deeper into the school and like what do we know now? And then there are the t the student facing pieces of AI. what Jared Horbath who wrote the Digital Delusion would tell you is like there should be no student facing pieces of AI because of some of the downstream effects of ed tech in education. He's one extreme. I can find just like probably twice as many people who are super excited about the impacts of AI in education. But you know

That's its owner piece. And then there's like the administrative functions of AI. So how how does AI, like any other business, how can AI help streamline or create business efficiencies on the back ends of schools that still require, you know, a human to literally go through and do the things?

And there's and then there's just kind of like the general, and it's where everybody starts. Like there's the data governance policy, like all of that stuff, these things up here and form that baseline. But it's you know, so there's a lot of levels to it. Boards should always be at the most strategic level, which to me gets more into this the just existential pieces of

speaker-1 (41:06.168)
how this is impacting schools and how we're thinking about it and communicating about it with parents. those are maybe go ahead.

speaker-0 (41:14.962)
Maybe coming back to the purpose, right? Like what's our purpose as an independent school to provide the what environment do we want to provide? And how does AI play a role in that?

speaker-1 (41:24.812)
Yeah, or not, right? Because you can't also ignore that these students are gonna inherit they can't just go to college and be told to use AI for the very first time, right? Like so what are some of the realities that they're getting, but also projecting forward, like what what are those skills that they're gonna need later in life to navigate this new space? and what's that gonna look like? Because it is all about ultimately having our students thrive, not just when they're

schools but for the long term. And so I think that's it's an exciting board conversation. It is it is not one that has an answer yet. And so it's going to be a continuous education. to your question in terms of board meetings, you know, a lot of our schools meet meet more than the NEIS board does just because school school life is, you know, it's complex day to day.

But even then, you know, a lot of schools have ways for boards to keep up with education, to share resources with them and certainly to share resources with them before they go into a conversation. And when you're serving on a board, you know, you're you're committing to putting in that time.

speaker-0 (42:34.274)
Yeah, that's another thing, right? Board members need to know that time commitment because that's something that gets missed. Yes. Yeah, they don't understand that. Yeah, it's not just the time in the room. Well, Debra, we have covered a lot of ground today. We started with thinking about your role as the president and being the steward of a of a strategic plan that's taking your organization forward and then thinking about how boards and

And play a role with the senior leadership team and what that relationship can look like. And now turning our attention to AI and how AI can be showing up both at a board conversation level, but also what are you thinking about for it when you think about it as a presence in your school or not? And I think you're right, there is no final answer, and there's probably no right answer from school to school. Depends on

you know, what you're trying to achieve and what you're trying to do with your students and the environment that you're trying to create. And that may be very different from one school to the next. I shared with you, you know, my example of going to a very different school than my brother went to. And it's the same thing, right? Like different schools will have a different place for that type of technology, which I think is exciting and fun to think about. I

speaker-1 (43:49.77)
I think that's like one of the most exciting things. you know, all of our schools are different and context matters. Like it it matters tremendously.

speaker-0 (43:58.124)
Yeah. And I think that actually is a great way to bring this back around to the idea of what does it take to get into alignment and to stay in alignment? And I think context always matters. And taking the time to create that context is so important. We talked about sometimes you have to let action precede clarity and you might have a bias to action, but you have to recognize those moments when it's time to step back and to create context and to help people understand.

the bigger picture so that they can make the sacrifices they're being asked to make or the contributions that they're being asked to make within that context and not just within the narrow vision of whatever's most important to them. And that goes for board members as well as staff members.

speaker-1 (44:41.75)
I absolutely agree. And it's you know, one thing that I think it's easy to forget, like every time you add new board members or you add new staff, it's new to them. so like when you're in your own context and you got your own shared language and things, like when you have new people joining, you always have to bring them along and kind of get them in that context, understanding that culture.

And that onboarding process, whether it's for board members or staff members, is crucial because you don't you don't want them feeling like they're spinning without without that shared context and understanding. It will take them a while to get up to speed, but you know, that's that is such a crucial step that we can't miss in the process.

speaker-0 (45:27.468)
And it does get skipped, I think, with board members. I see it a lot. Just like come to the nice board meeting. Exactly. So I appreciate that that call out for them. Well, we have two final questions that we ask everybody, Debra. And one is just sort of as a roundup, are there two or three really key takeaways in terms of what a leader should do if they're trying to create alignment with their team, with their board, with another group, whatever that might look like.

speaker-1 (45:32.854)
I'll figure it out like

speaker-0 (45:56.642)
What would be the two or three things you want to make sure a leader is paying attention to as they're trying to build alignment?

speaker-1 (46:06.126)
you know, I've shifted a little bit on this over time. I I do think taking the time to pay attention to and build culture and understanding what your culture is is crucial. I don't think I used to wait that as much as I used to. the other one is clarity and simplicity in communication. You know.

Getting people to read anything longer than, you know, five bullets on a list is very, very difficult. And getting them to remember more than three is really hard. So like

And that's hard when we worked in really complex spaces, but you have to get you have to get down to that that level of clarity and simplicity. It will become your shorthand and you need to understand like what's behind your shorthand. So when you are onboarding people, you can like unpack it for them. But I you know, I think particularly the larger your organization, when you're a leader of a larger organization.

Nobody's hearing from you the twenty five, thirty-five minute unpacking of something. So they they need to understand it, you know, in in fairly digestible bites. and to create that like that shared language. And then I think I'll just empathy. you know, when when when you're seeing people acting in unpredictable ways or ways that you just didn't expect.

To to sort of take a step back and say, okay, like what are they experiencing? I'm a big fan of the the scarf model. I don't know if you I'll I'll share that, I'll share the link with you. It kind of like we'll put it in the show notes. Yeah. So it's you know, and it kind of just walks through when people are acting a certain way, like what what feels under threat to them in that moment? so is it is it their success? Is it their feeling of fairness? Like there's a there's a whole bunch of them and it

speaker-1 (48:07.648)
It also has ways for you to kind of counterbalance that. So I think to to take a minute, you know, I think most people they want they want to do a good job, whether they're on staff or whether they're on a board, like they want to serve the organization. As you said, they want to be of service. so if they're if they're acting out the, you know, kind of pulling out your empathy lens and sort of saying, okay, like what is this person experiencing? Where what where what might we be missing here?

Or what might they need to kind of get them back into alignment. and not to ign ignore those things. Like I think it's easy to get a little jaded and to ignore some of that, but that's also where stuff can go sideways. So I those are three things that I think about on a on a very regular basis.

speaker-0 (48:53.066)
I love that you rounded us out on empathy and not getting frustrated and being willing to come back into the conversation over and over. Yeah. But don't let it take over, right? Yeah. Yeah. All right. Well, our final question is a dream along with me question. And it's if you could get any group of people, whether it's your staff or your family or your community or your membership or whatever this, whatever the construct is that you want to choose, if you could get them aligned to do something together.

speaker-1 (49:04.117)
Exactly.

speaker-0 (49:23.01)
What would that thing be?

speaker-1 (49:28.11)
that's I love that. I, you know, I I love the idea of like bringing together and my family could certainly be involved because they fall into this like curious people to go on a trip, like on a learning journey. I mean, for me, I would love to bring a bunch of curious people like into educational environments that they've just never thought about or seen before.

in different countries, all kinds of different levels of resources, and see just the exciting things that people have figured out and how much joy there can be in learning. And like what and to hear what their takeaways would be from doing that. and then to have time to really think, you know, sort of philosophically and existentially, like if we could rebuild education now.

Given like what you learn from that sort of, you know, travel and getting out there, experiential outing and where we think education is going and like the tensions we see in the future, like how would we rebuild education as whole? You know, we keep kind of shifting around the edges, you know, we talk a lot about higher education in this country. Like, if you could just start from ground zero, like what would that look like?

giving, you know, excellent things that are happening out there now. and like I said, my family can definitely be involved with that. But there's just like they're great thinkers in education who would be fun. And I like to bring contrary people into it. Like I want like, you know, a visionary, I want like a Michael Horn who loves to like kind of push on people in a direction. And then, you know, I want people who are like total traditionalists who are like, no, that's gonna make a hot mess of everything.

all of the structure we're trying to bring to learning and and have people kind of wrestle with those concepts. I just think it would be ridiculously fun.

speaker-0 (51:32.686)
I love that. I love that call to action, find joy in learning and being curious and going out and exploring the space of education and then coming back together and you know, the the the blue sky idea of if we could build it from the ground up, what would we build? Be fascinating to see what comes of that. If you ever pull that off, let me know and I'll jump in and be a part of it.

speaker-1 (51:52.438)
You you are welcome to come along, Julie. It'll be it'll be it'll be a long trip, but it'll be a good one.

speaker-0 (51:57.022)
Yeah. Well, you know, I always remember reading in Sandra Day O'Connor's autobiography, one of them, she talked about as a Supreme Court justice, you know, during their off season recess, I guess you call it, she would travel the world and she would go help in other judicial systems and learn about those systems and also try to bring them more into a democratic approach and how educational that was for her to

really see how justice gets handled in other parts of the world. And I think what you're saying saying is the same thing that educators who take the time to be curious and go learn about how education happens in other environments can gain invaluable insight. And I think that is what helps keep put people in alignment to shared goals around big strategies about how could we do this differently and what could it look like. They can fuel that excitement to to be willing to try things.

by seeing what other people are doing and what other people have discovered. So thank you for that call to action. And thank you for being a guest here on the Failure Gap. It's been really awesome to hear about your background and about your experiences and your thoughts on the power of aligned leadership and how we get there. So thank you so much for joining us.

speaker-1 (53:09.686)
I it's been such a pleasure. Thank you so much, Julie, for having me.

speaker-0 (53:12.462)
Of course, you know, a Kyracuse group we like to say to go fast, go alone, to go far, go together, and to go far fast, get aligned. And I think that's exactly what you're working on with the work that you're doing at at NAIS. So thank you for all you're doing for education in the United States and for independent schools as well. And with that, for all of our listeners, just a reminder to like and share this episode. Check out the show notes for some of the references that Debra provided. We'll be sure to get those out there. And we'll see you next time on the failure gap.