Read the full transcript of Episode 41 of the NAIS New View EDU podcast, which features a conversation with new NAIS President Debra P. Wilson. In this first school year of Debra’s tenure, she sits down with host Tim Fish to introduce herself to the NAIS community and share her personal journey with independent schools.
Tim Fish: Welcome back to a new school year, and a new season of New View EDU. You know, if you’re a longtime listener, you know that we have been on a quest to answer a simple, single question. What is the purpose of school? Now, at this moment, what do we need to be doing more of, and what do we need to let go of in order to provide our young people with the tools they need to thrive in a complex future?
In the first four seasons, we’ve discovered that agency—student agency, teacher agency—is a critical ingredient on this journey. In this season we’re going to dive deep into two more essential ingredients: creativity, and the notion of busting out of the box, doing things differently. Now, more than ever, we have got to get out of our “Now Town.”
We’re going to explore arts-based education, like the Chicago Academy for the Arts. We’re going to talk to the authors of a new book, “Creative Hustle.” We’re going to bring in thought leaders who are making education a global experience with place-based learning design. And we’ll get really practical with episodes to expand your toolbox, like a discussion with Dr. Catlin Tucker about blended learning and student-led learning. And, the return of our dear friend, Dr. Shimi Kang, who will help us grapple with new technologies and creating future-ready minds. I can’t wait, also, to end our season with a conversation with the most important people in education today: Our teachers.
So, I cannot think of a better way to kick things off than by talking with my friend and colleague Debra Wilson, the newly appointed president of NAIS. You know, prior to stepping into this role, Debra served as the president of the Southern Association of Independent Schools. In that work, Debra led an incredible team and supported hundreds of school heads, board members, and school leaders. And prior to that incredible work, she served as the general counsel at NAIS for 19 years.
You know, that’s where I got to know Debra. When I was working as the associate head of school at McDonogh School in Maryland, we would often find ourselves in sticky situations. And I learned quickly that a call to Debra could immediately get us unstuck. Her ability to get to the heart of the challenge, to ask good questions, and offer invaluable next step advice was amazing. And you know, it’s incredible. I’ll bet you that every school leader who’s listening right now has had the same experience that I had. I am not sure how one person can possibly answer so many calls.
It is such a joy to get going. Let’s kick off another season of New View EDU.
Debra, thank you so much for joining us today on New View EDU. Welcome to the podcast, and welcome back to NAIS. And thank you so much for giving us some of your time today.
Debra Wilson: Thank you so much, Tim. You know, I'm very excited to be back at NAIS and working with you and the fabulous team that we have at the association, so thank you. I'm excited to be here.
Tim Fish: So Debra, you know, you have spent time, over 20 years working in independent schools. You have worked with literally thousands of school leaders. And as I was thinking about getting ready for today, I was like, you know what? I bet there's a lot of people who don't know the full Debra Wilson story.
Where'd you grow up? Where'd you go to school? What was your journey like as a student? Feel free, tell us, introduce our listeners to your story.
Debra Wilson: It's so funny. I, I have found myself answering that question, like, I think you're right. People are like, you know, how in the world did you end up, you know, I've had sort of a weird life path, right? I grew up in Connecticut. I grew up in a little town called Norwich, Connecticut.
My, my dad and my mom actually grew up in a little mill town called Jewett City. Just a little outside of Norwich. Like Norwich is, you know, a metropolitan behemoth compared to Jewett City. I mean, all my, all of my grandparents, all my great grandparents came through Ellis Island. They all came from Poland.
Tim Fish: Wow.
Debra Wilson: Yeah, and they, my great grandparents all worked in mills and my grandparents actually all worked in mills, and my parents were the first generation to go to college. They were, you know, I'm from a big education family. We were very close with all of my grandparents, but particularly my paternal grandparents were around quite a bit.
My grandmother, my paternal grandmother, she actually had lost both of her parents by the time she was 12. And her, her father had, she lost her mom when she was about six, in the Spanish influenza. And her father had remarried. So when her father passed away when she was 12, she went to work in the mills.
She had a sixth grade education and it was time to go to work to support her stepmother and her half sister. And then my grandfather managed to finish eighth grade and then he went to work in the mills. And you know, they went through the Great Depression, you know, just really hard times. You know, when we, I, every once in a while, you know, if I'm feeling a little down, I think about how ridiculous they would find the things that get under my skin these days.
You probably have that experience.
Tim Fish: Same, same first world problems, right?
Debra Wilson: Yeah. Yeah. They, I mean, I mean, they would just shake— I mean then they used to shake their heads at us when we were teenagers. So but you know, they had four kids and they, my grandfather said, you know, there's not enough money to send the girls to college. And my grandmother said, oh no, if we're sending the boys to college, we're sending the girls to college. Because she'd been earning her own money since she was 12 years old.
She was like, yeah, I'm not debating this. This is just what we're doing. So you know, and I actually used to have her wedding picture in my office and I, and they had a little slit back there, and that's where they would save money for different kinds of things. So I actually still got that in my office and yeah, all four kids went to college. My aunt has a PhD in nursing. My uncle's a dentist. My mom, my dad was a gastroenterologist and my aunt was actually a teacher for many, many years and still, I think she just turned 80 or 81. And she actually still teaches, she does learning support for the public schools in Connecticut.
So, and you know, my mom, similar, she was an only, only child, but, first generation to go to college. And she also has a PhD in nursing, so big education family. And my parents divorced when I was 12, when my dad remarried. He married my stepmother who taught special ed in public schools in Connecticut for over 30 years. So.
Tim Fish: So education was it. It was part of the deal, part of how you grew up?
Debra Wilson: Yeah. You know, you and I track a lot of education trends, right? Like that's what we do. And so this whole trend of maybe kids don't go to college, like there are different paths and like, you know, Google hires you, pays for you to go to college. My grandparents would just be like clicking their tongues at us like, no, you don't hesitate before you go to college. You go to college.
Tim Fish: No, you go to college, you go to college. You sure do. You know, it's so, so interesting. My dad, you know, almost failed out of high school and then ended up convincing Drexel University to give him one semester to try him out. 'Cause they were, laughed at him when he first walked in the door. And he ended up working full-time all over the place.
And then did nine years of night school, four nights a week on the train out of Trenton, New Jersey, down to Philadelphia. And, you know, two small kids and that, that journey story of what it looks like, you know, super inspiring to me. And it sounds like you have that same inspiration in your, in your childhood.
So then you've got this amazing education family and you go to law school. So, so what's up with, so what's up with all that and how did that end up calling you back to education?
Debra Wilson: You know, so I went to, actually to public school through sixth grade. And then I went to the Williams School in New London, Connecticut. And my two older siblings were there before me. And that was really our first educational experience in independent schools. My cousins who also grew up in Connecticut, they went to Choate, they lived right near Choate.
They were both day students there. And then, I mean, I, I actually went south, like I was ready to just get out of Dodge. I was, I was done with being in the Northeast and you know, this was radical. I mean, from the Williams School, I think I had 38 people in my graduating class, you know, and when you've all been together for six years, it's a really long time.
And most people go to Boston, further up into New England. If you're radical, you go to DC. Not me. Like I went to a mountain in Tennessee, you know, which was incredible, right? I mean, it was. It's hard to go from coastal Connecticut, you know? But when my parents separated, my mom spent a lot of time in Mystic and I spent summers working at Mystic Seaport, and if you've seen Mystic Pizza, that's Mystic, Connecticut.
And yeah, I just was ready to go. So I went to a mountain in Tennessee and studied English for four years. And it was just, it was, I mean, I feel like everybody should move out of their culture that they grew up in, at some point in time. Like it just gives you a completely different perspective.
Tim Fish: One of our themes for this season, Debra, is get out of the box. Right? Get out of your own box, see things differently. And you know, the School of the South, Sewanee is not a small campus if I understand things correctly. Right?
Debra Wilson: It's getting, it's getting bigger every day. There's, it was 10,000 acres when I was up there. Now I think it's 14 or 16,000 acres, and it's, it's, it's one of the most beautiful schools in the United States. It's beautiful, and, and it's been fascinating. I, I've been involved with it in a few different ways, but to watch it wrestle with its history and to be a part of some of those conversations, you know, it's you know, I mean the South is a, it's a fascinating place. I, I'm glad to have spent time there, but yeah, then I had a couple years and then I went to law school. And I loved law school.
I don't know how many people feel that way about law school, but I mean, I, I loved it. I love my classmates, I love my professors. I'm still in touch with professors from law school, college, high school, and even elementary school. I've just had so many fabulous educators.
Tim Fish: So, you know, the, the framing question that has kept this podcast going, it started off in the beginning with these amazing conversations when Lisa Kay Solomon was with us, and the thing that was driving us was this idea like, what's the purpose of school? You know, if you go back, you know, Committee of 10, 130 years ago, desks in rows, Carnegie units, you know, curriculum, knowledge, skills for the Industrial Revolution.
So you say, all right, well maybe that stuff's not so relevant today. So what is the purpose of school today? Why don't we just box the thing up and close it down and move on to something else, right? Because I'm actually a believer that we've never needed school more than we need it now. And I think the purpose is in evolution.
Debra Wilson: Yeah. You know, I, I actually think the purpose of school is actually what makes me really excited about education right now, particularly for independent schools. Education now really is about educating and helping grow the whole child. More so than it's ever been. Right? And I'm fascinated by like, the Center for Curriculum Redesign, you know, people who are coming up with different frameworks about how to talk about a mastery transcript consortium.
Like how, like what are we talking about these, you know, these, the knowledge, skills, traits, characteristics, like that whole thing is on the table now. And I think it's actually become more crucial than ever that we, we articulate those things because it ties. Right. It's hard to find an independent school with a mission that doesn't talk about educating the whole child and laying out at least a couple of these things.
But I think how we articulate that, how we bring that to life, how we hire for those, those experiences in the people that we hire. Right? I mean, you're the people that are in the classrooms having these relationships, you know, everybody's, you know, concerned that AI is like the education Armageddon. I actually don't think it is.
I think it allows teachers to double down on the relationships piece. And to really demonstrate the kind of outcomes that we're looking for in terms of people. And, you know, the diversity of our schools gives parents so many options in terms of what aligns with their values, what are they thinking about as they're raising their kids.
I just, I think that's getting more crucial, not less. I mean, as, as knowledge and content become, you know, ever available. You know, you and I now carry computers in our pocket five times as powerful as anything we saw as kids, right? Easily five times. Our, our Apple two plus was not any kind of learning machine other than typing.
You know, I think these, these other pieces are just that much more crucial. I was talking to a college president the other day and they're talking about these, these majors where, you know, students show up and they can just choose any classes and then the school will just tell them what their major was basically when it's all done.
I actually, I mean, I think that we should be requiring students to really think about morality and ethics, and it's the how to think, not what to think, but knowing that it's crucial to actually be thinking about these things as the, as just the different projects and outcomes they work on, can affect humanity at a greater scale than they ever could.
So I, I do, I think a lot about that, but I think it's really exciting because I think it's the holistic picture of how we grow people.
Tim Fish: Yeah, I think you're so right. I think you're so right. I think when we, when you take out what was in, long time in the center, this content and skills and curriculum and stuff, right? Stuff of school, and you say, OK, there's other ways to get to that. I'm not saying that we don't do it anyway that we do in school, but there's the other, what do you put in its place?
Right? And what I'm hearing from you is the whole child goes in the middle. That's what we really focus on. And I know for you, wellbeing and the wellbeing of students has been a, a key part of something you've been very interested in exploring. And I'm curious about what are you finding in that work and what are you seeing out in our schools that excites you, that gets you really fired up for, for some of this other good stuff that's going on?
Debra Wilson: I think I get, I get excited about that. I, frankly, I get a little worried about it too. Right. So the, the skills that you need to live a healthy life right now, I just think are very different than they were, you know, even 15 or 20 years ago. You just look at the number of people who are in hybrid work things, or they're always, you know, teleworking.
You know, we know that human connection's actually really important for people. It's hard to do that if you're working at your computer on a desk in your house eight to 12 hours a day. Right. So, you know, and, and frankly, it's not great for communities if we lose these connections with each other. You know?
I mean, it's, it's like butterfly wings, right? You know, a couple things go wrong. The whole thing sort of falls apart. So, you know, how are we thinking about that? And we look at not just what are these kids going to be doing in the future, but what does, what does a Wednesday look like? You know, what is, what is their life experience actually going to be like and how do we help them get a handle on what, for them, makes a healthy life?
I mean, you and I did some work on the Gallup studies a few years ago that NAIS got, right. And it talks about the six or eight things you do in college, right, that directly correlate with wellness later.
And frankly, a lot of them are getting on campus, getting engaged, getting engaged in extracurriculars. There's nothing in there about grades. There's nothing in there about GPA correlating with later happiness. But there's a lot in there about, you know, just, did you participate in things? Did you do a sport? Were you involved in clubs? You know, did you do a capstone type project? Those kinds of things were, did you have a mentor you really connected with and really believed in you? I actually think all those things are just that much more important as you grow up and you get a job and you move out.
I mean, I, you and I both have kids. We've shared a lot of stories about our kids together. And you know, watching my son, he is in college now and he's got like his first big summer internship, and I just love seeing him just throw himself in there. And he has done the same thing with college. And you know, you know those are the things that lead to healthier outcomes later.
And there's so much more data and information than we had, you know, growing up in high school in the eighties. Right. Like that, just nobody was having that conversation. But if we know it now, we should be teaching it.
Tim Fish: That's so true. It's so true. And you know, it makes me think about, sort of what that, what that structure, as you said, is going to need to look like. What does a Wednesday look like? Right. And, and you know, I was, been reading The Good Life. I don't know if you've read The Good Life, that book about the Harvard Social Science Experiment.
Debra Wilson: Yes.
Tim Fish: It's an awesome study, right. I, it goes back to 1938 when it started and they've done like generations and the whole thing. Right. I also like the book of, for people who are listening, and actually they tell you how they did the study in more detail than I was expecting. Right.
But they boil it all down.They're like, look, here's the thing. The people of this whole study who lived really happy lives and fulfilled lives, had great relationships.That was it. They were like, that was the thing. Right.
Debra Wilson: When I, when I talk about this, like I go through, there's like, That's the number one thing. Right. And then there's like some other stuff like, you know, you don't drink too much, you don't smoke. Like there's like all, but but the relationship piece—
Tim Fish: Yeah, it's—
Debra Wilson: —at the end of the day. Yeah.
Tim Fish: More important than money, more important than success, more, it's just, it's like that's the thing, right? And, and so for me it's that notion of like, when you look at the whole student, like you were talking about, how do we build, what does school look like? What does Wednesday look like? When you really put that at the center, right?
And I, and when I look at school, I think we, you know, I think there's a lot we're doing that's really good. I think the people that are working with our young people are committed individuals who are having an incredible impact on their, I see it every single day. Right.
Debra Wilson: Every single day. Yes.
Tim Fish: And at the same time, you know, getting back to sort of the Matthew Barzun thing that we talked about on the cons—on this thing recently, this notion of a constellation, and a constellation is interdependent people. You are seen. You are known. And you are needed. Right. And that's the thing, right, that we've talked about before. I don't know that we're hitting hard enough in our schools. I don't know that enough kids show up every day feeling like they're really needed in the community.
Debra Wilson: There's this wonderful woman, her name's Jennie Wallace. She's got a new book coming out this summer. It's called Never Enough: When Achievement Culture Turns Toxic And What to Do About It.
And she's really amazing in a whole bunch of different ways. You know, she writes for the Wall Street Journal, she writes for the Washington Post. She worked on 60 Minutes for a long time. But it's actually like, a lot of her message is around mattering, like why that matters to people, but also why it's so important for kids. Like kids need to feel like they matter. And part of mattering is, yeah, are you needed? Like…
Tim Fish: Yeah. Is there some connection here? Right? Am I invisible? Right? Invisibility for a young person is the wor— like the worst thing, right?
Debra Wilson: Yeah. Although I got a 13-year-old who sometimes wishes she was invisible.
Tim Fish: Yeah, there you go. There you go. Well, invisibility on my terms, maybe is the way we'll put it. Maybe, maybe we'll say invisibility on my terms, because you're right, they do like invisibility. Doors are a thing that people love.
You know, I'm curious, Debra, of all the schools, I mean, you've literally, you've been in hundreds if not thousands of schools, and I'm curious, when you look at all the independent schools, what's the secret sauce of independent schools?
What do independent schools have that, that just makes them unique? Any thoughts on that?
Debra Wilson: You know, I think it, you know, the secret sauce is a little different from school to school. Like, I mean, I, I really do think it depends, context really matters. There is that…do people feel known and seen? And when I, when I say that, it's not just the kids, but it's the individual staff members, it's the parents.
Like, what message are they receiving all of the time? And that really leads to greater connectivity. And it tends to lead to happier encounters. Right. And it's, it always impresses me, you know, I am sort of a recovering attorney and so, you know, when I show up on campus, I, I usually show up a little bit early and I, and I try not to go in the front door because I'm just curious to see if school's really sort of secure.
I know that sounds terrible, but I, I, it's something I've done.
Tim Fish: It's a great idea, it's something I'm going to pick up actually.
Debra Wilson: And a lot of times, you know, I'll talk to an adult, but a lot of times I'll ask kids, I'll say, you know, "Hey, I'm a little bit lost. This is what I'm looking for." Just to see like, what's, you know, how do kids interact with strangers?
You know, adults? Like, do they like, walk with me? They're not letting just some random stranger wander around their campus, but, you know, just what does, what does that student interaction look like? And, and it always impresses me, the schools where kids are like, oh, you know, I, I, you know, I think I know where you're supposed to go. Let me walk over here because my friend is going to that other building and she can walk you over there. because I know she's going that, like, they kind of almost like pass you like a baton and they've got kinda that community feeling like, and it's, and and I, I love that sensation.
And, and it's you know, just that, that recognition and particularly when they see me when they're like, yeah, not quite, you don't belong here, but, but I know you're not in my regular spin. You're not somebody I normally see. And they're still very welcoming, but they're also, you know, making sure I'm getting to where I'm going. The adults are making sure I'm not just wandering around campus. Like it's, I don't know. It's, it is a unique feeling.
But I haven't found, like, it's not one educational philosophy. It's not do you have a wall or not, or do you have a gate or like, whatever the thing is. I mean, it really, that's something that seems to transcend our, transcend our schools, regardless of kind of those like fundamental baselines that you tend to think about.
Tim Fish: I, I think you're spot on. I think it's exactly what I feel, you know, when I ask, when I ask schools, you know, what makes you unique or what makes you special? The number one thing, I don't know. What's the number one thing you hear when you ask that question? Right? For me, it's community. Each community is different. Each community is unique. It has its own sort of secret sauce as you, as I think you so rightly said.
But it's this, it's this interwoven human experience that I think is so much a part of what makes our schools so great. And I guess for me it's like, how do we double down on that? How do we continue to do that really, really well? Right? What does it look like if we're going to really, really build that community?
I'm going to ask you to switch gears for a moment and just, Think as a mom with your own kids going through school, you're in this great moment. You have kids in college, you have kids still in K-12. When has school worked really well for your kids and when has it not worked so well for your kids? Maybe?
Debra Wilson: Yeah, well, you know, it's, it's so interesting because it actually ties in a little bit to what you've just said. So all of my kids have gone to Montessori school through eighth grade. So our youngest one is finishing seventh grade. And that, as you know, I'm a little bit of a glutton for punishment. So the first time I ever went into like a, I mean I did Montessori preschool, but the first time I went into a Montessori school as an adult, it made me really uncomfortable.
Like it, all of my Type A personality, things like, you know, it was, I was, I was like a cat. I was a cat being pet the wrong way. But I was all, you know, we have two girls and so I'm like, you know, this ambiguity is really good for kids, and it's really good for girls in particular right now in education.
And you know, my husband, I think, thought I was a little bit crazy, but he was willing to kind of roll with it. My in-laws really thought I was crazy, but, but they, they went with it and the school does this very sweet bridging ceremony when they go from lower elementary to upper elementary. And my mom and my mother-in-law were sitting next to me at one of these things and they're both crying because like the teachers are reading these like individual things about each student, and they're both like kind of traumatized by their own experience in school, because you know, I won't even go into what that looked like in the fifties. But they, you know, they just both got so emotional about it and I was like, what is going on with you two? And they said, we've just never seen anything like this before.
And so they, it had that mattering piece, it had the skills piece and the building out the community. My, all three kids project plan better than most adults I've ever met. They certainly project plan better than I do. Like they just have a different set of skills, and that has really worked for them in a lot of ways.
I think one place that school has struggled a little bit is as it's gotten bigger, it's hard to scale some of that. So like what you're saying about community, right? Like context matters and how you hold some of this together. I mean, I think they've, I think they've done it as well as they could, given that they're getting bigger. But it's really hard.
I, I was talking to somebody the other day and she talked about moving at the speed of trust, and I love that idea. Right? Like, I mean, it just totally, I was like, wow, I like that. I'm going to just keep circling back to that. Like what is that, moving at the speed of trust? And some of it is moving at the speed of trust, but also moving at the speed of your culture, right?
Like, how do you get your community to hang together as maybe you're going through growing pains or you're, maybe you're deciding to get smaller, like whatever your thing is, like how does that move? And that, I think, is really hard and is, you know, one of the things I talk about with education, we adults can mess around with us all we want. Every kid's only got one shot at it. So, you know, if they have a bad teacher placement three years in a row, they're 50% behind their peers. Like that's, I mean, that's, that's just research. Like that's, there's just numbers. And so we don't really have time to play around with this, so like, how do we hold those things really sacred?
But I mean, I, educators just impress me no end, you know, particularly teachers, day in, day out. One of my neighbors is a, she's the head of a middle school and I'm like, you know, it's, it's both the bravest job and just, I mean, what an incredible amount of responsibility.
Tim Fish: That is so true. You know, I love what you were saying earlier also around this, this idea of ambiguity and how important ambiguity is. And in particular, ambiguity with girls. I'm wondering, can we click in on that a little bit? I'd love to hear a little bit more about that. Cause it, it's picking up on a theme that we've been finding in this, in this season.
So tell me a little bit more about that.
Debra Wilson: Well, I mean, it's part of life, right? Like it's part of, you know, we do this at NAIS, right? Like, one of the things, you know, and I, as far as I know, NAIS still does it, like, you know, we have an evaluation question every year, like, what's your do over, like, what would be your do over, right? And a lot of those things, at least in my experience, are not, "Wow, that went like, rip roaringly terrible."
But it's more like I just, that just didn't go the way that I want. Like you, you know what I mean? Like, you just get that kinda like, I mean like in, in a, more than you need to know. Like, I grade myself on stuff, like I'll do a talk and be like, yeah, that was like B-plus level. Like, you know, and you, you want to bring your A game every time, but for whatever reason, sometimes it just doesn't.
But like, it's just that feeling, right? And like my kids would come home from Montessori school. There's not many grades at Montessori school until they get up towards adolescence, right? And they would show me a project or something and I would say, you know, well, so tell me about that. And I'm like, well, and I, and, and they said, well, what do you think?
And I said, well, do you feel like you did the best you could do? And like, you know, and that would get them all riled up. They still get really riled up at me when I actually say things like this. But I'm like, that's ultimately like you kind of have to live with yourself on the job that you do and that, you know, what you bring to the table.
And we can't all bring our A game. And as you and I both know, you can do an A job six weeks later than you really needed it. That's not an A anymore. That's like a D-plus because it, you needed it six weeks ago. And I think as people are working more virtually or they're working with virtual teams or like you're just doing different kinds of things, your ability to regulate yourself and to understand what you're bringing and what needs to be brought all the time, and to function with that ambiguity, or to reach out if something's too ambiguous, to get more guidelines or to get a better feeling from the team, like what we want our outcomes to be.
That's going to be crucial. Like I, you know, if you can't do that and you can't communicate that, I don't, I think this next 50 years, those are going to be really, really hard.
Tim Fish: So let's switch gears for a moment. So you, as many of our listeners know, you literally wrote the book on good governance for NAIS, right? Like I don't mean that figuratively, I mean, literally.
Like you, you know this topic so well. You have spent time with so many boards and you have gotten called so many times when governance goes wrong, or is on the way to going wrong.
I'm really interested, Debra, on your sense of what are the keys that, you know, let's do it this way. If you were to think about the good governance bumper sticker, right, on the good governance bumper sticker, things to do and things not to do, fitting it on a bumper sticker or on a t-shirt, what would you tell if we were going to be trying to make that merch for NAIS?
Debra Wilson: Yeah. Yeah. I don't know if I can do it on a bumper sticker. I might be able to do it in like, you know, an airplane fold out. You, you know, and I'm so excited to work on this again with the NAIS team because, you know, I've spent a lot of time across SAIS, SAIS has some of the biggest and smallest schools in the United States.
And I really do think the size of the schools, or the sophistication of the business practices in, in a school actually matter. Like what, in terms of what's happening there from a governance standpoint. But when I think about governance these days, after having been in so many schools doing governance workshops for the last four years, you can't skip the orientation and training.
Like some of it is just basics. It's not very sexy, but you just have to do it. I'm a big fan of doing new board training with the rest of the board because you get people talking about cultural norms, you know, go through those case studies, do those tabletop exercises and let the new trustees hear from the rest of the board. This is how we do it. You know, so if a parent letter goes to a whole board of a school with 250 kids, that looks one way. If a parent letter goes to the whole board of a school with 2,600 kids, it kind of looks a little bit different.
It's good to talk about what those norms are. One is not more right or wrong than the other. Some of it is just staffing resources. This is what it looks like, and just basic understanding piece. So, that orientation and training, do it every year. Never skip it. I don't care what happens. And it's a good refresher for everybody else because you're going to have somebody who missed it the year before.
Really thoughtful recruiting for cat herding skills. You need to have a couple people on the board who have the gravitas and just self-esteem, and they're just not, frankly, too worried about making other people mad, that they can go in and tell somebody if they've jumped the rails. It only takes one board member. I mean, I've been with a board, they're in killer shape. Like we were doing, you know, governance 301. Like they're, you just get like one or two people to jump the board off the rails and suddenly they're deep in the weeds. They're holding, you know, I don't know, parentdinner complaint sessions at their house. Like, I mean, it just goes totally off the rails.
So, you know, just people and people who are willing to like, spend their political chips for the school. Really good business practices. And again, it's not sexy. Like at the beginning of the year, you send out those outlook invites for every board meeting, every committee meeting. Like just get those on the table. Everybody knows what they are, because that's where our trustees are for the most part, right? Like they're using their Google calendars or they're using Outlook. Like just get that all clean, all of it planned out, ready to go. So everybody kind of knows what they're supposed to be doing.
And the complement to that is the board's not going to govern itself. So I talk to a lot of heads, and I totally respect it because boards take a lot of time. They're like, well, the board's just not doing anything. You have to give them structure. Like, I don't care if it's like the chair of your English department is like just helping send out reminders for the governance committee to actually like, meet and hold it to a calendar.
I mean, Tim, you know, we run the NAIS board, and we do something similar to SAIS. We have staff liaisons for every committee. Just to make sure that those things are happening. There's an agenda, like everything happens the same way every time. And I mean, you just need to provide that organization. It's, it is a rare board in my experience that is going to do that by itself. Like, it just, it's really, really rare, and, you know, hope is not a strategy. So, you know, give yourself that structure.
And then the last one is actually a piece of advice I got from a former NAIS board member, and it's really to have a strategic question for every board meeting, but know what mode you want the board to be in, like, and really call it out. Say, well, we really need to hear, we need to hear the board discuss this. So educate the board, whether it's pre-readings, or pre-readings plus a little front end presentation. We need to hear you discuss this. And then it might go back to committee, and then it might come back to the board for the vote.
And then you say, we need you to vote, and these are the two or three options. Here's the way we're looking at these things, right? I call that bread crumbing. When you have a few different board meetings and it kind of, you know, it evolves over time into a vote in the long term, but you know, that you call it out. You're focused strategically to begin with. Not a boatload of reports, but like, this is our strategic question. This is our strategic issue, but really calling out that mode of this is exactly what we need from the board. So the board knows what it's trying to do, right? Like if you kind of just let people swirl in conversation, there's a good chance you're not going to get to an end.
But just to call it out like, Hey, we really need to talk about the board calendar. This is what it looked like before. This is what we've tried for a couple years. Let's get some feedback on this. And then it goes back to governance committee or whatever it is. So I don't... schools that do those things tend to be able to keep it in the road. And you never know what's going to come up at any given point in time. Right. And I'm not seeing any signs over the next three years that that's going to calm down anytime soon, but, some of these, I think they're just kind of practical, good norms that I see healthy boards doing again and again and again.
And I mean, you know, you talk to a lot of boards, you know who those couple of people are, with the gravitas to keep it, everybody on the straight and narrow. Like a good chunk of the board will look sideways at one of those people, you know, if something starts to go because they know that person is going to jump in and be like, Hey, I think we need to take it up to 20,000 feet again.
Tim Fish: I love it. Boy in there, I heard several bumper stickers. Actually, I think we have a whole series. I think we can have Debra's bumper sticker series. Number one was pay attention to the fundamentals, right? It's not sexy. Do the work. That's that. That's that bumper sticker, right? Do it on finance. Do it on orientation. Do it on foundational concepts, right?
So the other one is, you know, governance committee matters. Right? Pick wisely, right? That's another one that I think I heard you say.
Debra Wilson: Look for succession planning. Like what do, what do you like to see in these people?
Tim Fish: Yes. The other one is have a process. Right? Have a process. Be really deliberate about, Hey, we need to hear your feedback from this. Right? I love, leave the breadcrumbs, lead them to a path. Lead them to a decision. Right. So I mean, great, great ideas that you've just shared. I'm, I think that that's going to be really valuable for our folks.
And the other piece for me that I'm hearing you say is like, look, good governance is not rocket science, right? This is, you can do this, people can do this, you can have a, a highly effective board. Culture matters is the other one that I think I heard you say. Right, and pay attention to your culture. Work on your culture.
Debra Wilson: Pay attention to your culture. It's, Rob Evans and Michael Thompson laugh at me every time I say this. Like, now is not the time for like the hip, sexy, cool board selections. Like you want good, smart, thoughtful, solid people doing good, smart, solid, thoughtful work. Bright shiny objects, like, they can, they can jump you right off the tracks. You know, and you can bring in those conversations in a lot of other places and a lot of other ways, but, you know, yeah. Like that kind of traditional, basic, not so sexy, like, we just, we're going to do really good work day after day, week after week, month after month, year after year, is what you're going for most of the time.
So yeah. Yeah. I'm sorry it's not more interesting.
Tim Fish: No, I love it. So let's keep, let's keep playing our, our bumper sticker game and let's, let's push it to school heads. And you certainly have been there for so many and have answered the call from so many. What are those things that you think are essential skills for effective, really effective school heads today?
Debra Wilson: Yeah. Such a good question. That, that relational leadership, that ability to, to have relationships, to hold relationships, to build trust and to keep it. You know, and it is, if anybody's a sailor, it's like planing a sailboat, like right, like you're just always kind of riding on that edge. I think is really critical.
One thing I think is getting more and more important for heads as they go through searches, they look for new schools, is you know, I, I say that, you know, people look like their dogs. You and I have had this conversation too. I look a lot like both of my dogs and they don't look anything like each other.
But heads look like their schools. Like they're like, you can tell when like, people are really jiving and just, you know, how your personal values align with the school's values and the school's mission and how those things click together or where they're not quite in alignment, that you know that you're OK with that and you're sticking with the school's mission in that leadership role.
You know, so many heads I've talked to, they're like, well, I really thought I could change this. I'm like, it's kinda like marrying your spouse. You're not going to change that person either. Like, you know, if it's a fundamental thing about a school, like, so that, that level of self-awareness, that recognition, and I think heads are getting better about it.
You know, we launched the Head of School database, headsearch.org a couple years ago. And so people call me about, you know, schools that are open and I'll follow up and say, you know, hey, you know what happened with that search? And, and so I've talked to some heads and they're like, you know, I went through the first couple rounds and I'm not going to be the person for them.
Like, it's, either doesn't align with my skills. I just don't, you know, I don't feel like the values clicking the way that, that they should, because these are lifestyle jobs. These are not, you know, it's not a, it's not a nine to five, it's not a widget factory. Like you are living this, and you're having a huge impact on, you know, the students and the families and the people who work there. Like, they’re such incredibly human endeavors. So that level of self-awareness and understanding going into this and doing this work, I just think is crucial.
And then the third one, I think is something Donna has written a lot about in terms of adaptability, right? That ability to, to kind of pivot, to understand like where you're going to need to flex, where you need to, you know, be consistent, be solid. I really, that's going to become more crucial over time too. And we've seen people have to use that over the last, you know, three years, in ways they've never had to use it before.
So, you know, I think those are three things that I'm seeing. And good communication, by the way, just cuts across all of it. You know, if that's like one of your personal Achilles heels, like you want to make sure that you're working on that, or you've got somebody who's kind of got your back and can help you with that, if you know that's one of your weaknesses.
Tim Fish: Yeah. I love it. Thank you, Debra. That whole notion there of like, pick the school. Like this notion of the search is two way. Right? And is it going to be a fit? And, and this idea of like, and I think for aspiring heads in particular, there's kind of, I just, I just gotta get one.
And, and like, no, no, no. Right. Like really pay attention to that and to find, and, and what I've also heard often from heads is this idea of like, the perfect school is not always the best school, right? The one that's got the most stable enrollment and the most stable finances and the most, right?
It may, like, those things on the surface may be great, But underneath it may not be the right fit. And, and on the flip side, a school that's got some work to do, right? A fixer upper in some ways, if you will, but has that cultural fit and alignment, bring it on.
Debra Wilson: And what’s going to, like, I mean, when you get up in the morning, like what's going to excite you? You know? I mean, every morning you're going to wake up and you're going to go do this thing, you know, and every, everything, every leadership job, I mean, heck, every job, but every leadership job in particular has a set of problems.
Right. And just, are those the problems that you want to go solve? Like do you feel fired up about solving those problems? For that school in that context, like, is that really exciting to you? Or is that going to like, chip away at the back of your soul on a regular basis after the first like six months of honeymoon kind of wears off? And you know, the, I mean those are really important questions I think in almost any job, but particularly in these jobs, because you know, as heads, you go to the grocery store, you're running into parents.
Like you can't, I mean, it is, you are living it. It's really hard to get away from. You know, it's so, I, I think, yeah, and I, I like the fixer upper. I mean, I think, you know, if it's, if it aligns, if everything else is clicking and, you know, maybe you have to get staff reengaged. Maybe there's some hiring challenges. You know, if you can see past some of that. But the bones are really good and they're what you're looking for.
Tim Fish: Mm. Love it. Love it. So our last question, we could talk all day. This has been so much fun, is what's on your reading list? You know, what's on your, what's on your pile right now? Because I know you are always, always reading. So what do you, what do you got for us?
Debra Wilson: Dude, I got, I have so many books that I'm reading. So I've got Killers of the Flower Moon, do you know about this book?
So it's about a Native American tribe and they're basically like pushed into Oklahoma. The chief of the tribe at the time basically says, yeah, like, we'll, we'll, we'll be happy to take this, just sad piece of real estate out in Oklahoma, right? Nobody's going to push us any further. But he is, you know, he's no dummy, so they actually maintain the mineral rights and needless to say, oil, they become incredibly wealthy.
But it's the story of these crazy murders of these Native Americans on their land. Hoover's involved. There's all these investigations, like several investigators are murdered late, and it's all, it's a true story. And yeah, no, it's really, really wild. So I've just started, I'm only a few pages into that, but I'm really, I, I love a good mystery.
I love fiction, I love nonfiction, whatever. I mentioned Jennie Wallace's book Never Enough: When Achievement Culture Becomes Toxic And What To Do About It. And then Jean Twenge's book Generations, so fascinated by the generations thing. And, and I worry about it a little bit too, particularly with, you know, you and I didn't even get to talk about AI, but how that's going to play out across generations, and how the generations are going to play together going forward.
Tim Fish:I love those book choices. And I think, I think you're right.
I think you're, I think you're, this notion of the generations is going to be so interesting. The next time we're going to have to dig in on the workplace and think about the sustainability of the workplace. Not a question we were able to get to today. And there was one of the, one, the many questions I have left on the sidelines that I would love to talk with you about.
Debra, thank you for giving us some time out of your incredibly busy schedule. What a great conversation.
Debra Wilson: Well, I look forward to, to many more in the years to come, Tim. So thank you for having me on, and we'll definitely do it again.