In a November 1992 interview with the Beaver student newspaper, Head of School Peter Hutton—then in his first year—said he was not afraid of change and would always be working to “improve the conditions and education at Beaver.” After 28 years of doing just that, Hutton is stepping down this June. Journalist and alumnus Jonathan Soroff (Class of 1983) recently sat down with Hutton for a Q&A about his leadership, the challenges he faced, and his takeaways from nearly three decades on Hammond Street.

Jonathan Soroff: What’s the very first thing you’re going to do when you finally hang up your Head of School hat?
Peter Hutton: Get into my Mustang, pop the top down, crank up the Van Morrison, and drive to Martha’s Vineyard. That’s a true fact.

Good plan! So what kind of student were you when you were in school?
Not good. I was a lousy student. I took two laps in eighth grade. You know, now, when kids are really good athletes, they say they “reclassify” and stay back. So, I just tell people, “I reclassified; I wasn’t held back.” But I wasn’t a student. They didn’t like to call it the dumb section, but we always saw it for what it was. I would sit in the seventh grade, and look around the room, and we were all on the hockey team, so I knew where I was. School really didn’t work very well for me. I was a frequent flyer in Friday detention.

To what do you attribute your ability to relate to students and gain their trust?
You know, I think people generally go into education because they were inspired by someone or something, and/or they’re really good at school. I went into education for the opposite reason, because I thought school could be a lot better for kids. And that’s what motivated me. I think that allows me to see all kinds of kids in different ways and different lights. I know every kid doesn’t experience school in the same way, nor should they. That’s not a great goal. As a kid, I got in all types of trouble. I messed around. I was a knucklehead. And that helps me. I love kids who are doing really well, but I can relate to the ones who aren’t.

“I went into education because I thought school could be a lot better for kids.”

Was there ever a student that you just didn’t like, and how did you handle it?
No. I can’t imagine not liking a kid. Kids can do impulsive things. They can do a lot of things you wish they didn’t do. But there’s always a reason for it. It’s not that they’re “bad.” Maybe they’re troubled, or unhappy about something, messed up about something. And you’ve just gotta take a deep breath, and try to put yourself in their position. And then maybe you can figure out what’s gone wrong.

What was the most embarrassing or awkward moment of your career as Head of School?
[Chuckles] There have been a lot, but I’ll tell you one. It was like my first year here, and the school was having a pretty hard time. The building was in bad shape, nothing was working. So after school, I was watching the Middle School musical in Bradley Hall, and I was standing up in the balcony. All of a sudden, the whole stage went black. I’m thinking the power went out, and I’m cursing how run-down the school is … until I realized that I’d kicked the plug for the lights out of its socket, and it was all my fault.

Thing you’ll miss the most?
Most obviously, the kids. They’re funny and smart, and they challenge you and surprise you and do great things and I’ll miss all that terribly. And although it’s a move to doing something new, the one thing I know I’ve got to do is work with really, really smart, and really, really interesting people, because we’ve got that here. The faculty. All the passionate trustees over the years. So, for me, I’ve got to keep working with people who are a lot smarter than I am.

“The head of any organization needs to embrace a certain level of risk. You have to be fearless and optimistic at the same time. Negativity can spread in an organization, but optimism can, too.”

What was your most emotional experience as head of school, with a student, teacher, or parent?
Unfortunately, that’s kind of easy to answer. We had a student, Alex Cohn die very, very, suddenly, in March of 2007, and it was awful. We gave the kids as much time and space as they needed. It happened right before Spring Break. We didn’t even pretend for a second that we were going to have normal school days anytime soon. It was obviously hard for the teachers, too, and they had to try and help the kids at the same time as they were trying to get through it. We didn’t bring in outside grief counselors to work with the kids; they wanted to sit and talk with people they knew and trusted, and I think we gave them a lot of space to do that.

What’s the trait that you think makes a great Head of School?
I think it’s more about leadership in general. I think the problem at a lot of schools is that education is a very risk averse sector. But I think the head of any organization needs to embrace a certain level of risk. If you’re a leader, it means you’ve got a point of view, and you’ve got to be willing to own it. I also think it’s important to be willing to unlearn and relearn along the way. You have to be fearless and optimistic at the same time. Negativity can spread in an organization, but optimism can, too.

You talk about Beaver as a brand. Isn’t that viewed as somewhat crass in the academic world?
Yeah. It is. Openly using terms like brand, or marketing, or saying that the student is a customer, I think a lot of people in education would think that’s crass, but I think it’s smart. One important thing about being a brand, and understanding your brand, and pushing your brand, is that it motivates you to assess yourself, and you’ve got to keep doing that. That’s a good thing, for the institution, and for the kids. So, I think being a brand is great. I always say that when you walk into a store, or a company, or anywhere, you should know exactly where you are and exactly what that place stands for. So we’ve been really relentless about that, in the way the school is set up physically, program design, and the social environment­­—everything is part of the brand. And when you walk into the school, you know you’re not in a run-of-the-mill, generic school.

Who are Beaver’s customers?
The students. And what I said earlier: it’s important to understand that not everybody experiences school in the same way, nor should they. That’s our customer. And that means that when you’re making decisions about issues, or programs, or ideas, you have to do it from the perspective of the student experience. What positive impact is that going to have on students.

One thing you’d do differently if you could?
One thing? [Sighs] You know, I’ve made a lot of mistakes. There is a lot I wish I could take back. Hiring mistakes. Mistakes we made around kids who got into trouble. There were times when I wasn’t flawless in making those decisions, and there are probably about 1,000 of those.

What was the state of the school when you took it over?
I’ll tell you the truth. It was pretty bad. But that was one of the things that attracted me to the school. It was in some trouble. It needed work. And yet the underpinnings, and the culture of the place, were attractive. There were 250 kids in the school, including just 25 in the class of ’95. They were great kids, but the building was falling apart. The admissions and application systems and fundraising weren’t there. And financially, we were running a $500,000 deficit on a $4 million budget. So there was a lot of work to do, but I believe we’ve been able to build the most forward-thinking, future-focused school in the area because of that. It demanded that we hold ourselves accountable, and to think about education in a way that other people weren’t. We might not be in such good shape now if we hadn’t been forced to do that.

How do you feel like you’re leaving it?
Well, there’s always work to be done. There are programs we can still keep working on. I think we need to upgrade our athletic program, and build our endowment. But this is the strongest faculty we’ve had in my whole time here. It’s the strongest management team we’ve had in my whole time here. We have an incredibly strong Board of Trustees. And that’s key. It’s critical. We’re poised to do some great fund-raising in the years ahead. So, am I feeling good? Yes. There are still a lot of things on my to-do list, but now it’s Kim’s to-do list.

“The kids are only [at Beaver] for three or seven years. They’ve got to have a dynamic, forward-moving school for all that time. That’s fun, but it’s hard. It’s much easier to be conventional.”

Biggest thing you have had to tackle as Head of School?
For me, it’s all about challenging the status quo. Continuing to build a culture, and really keep all of us cognizant of the fact that while education is a very risk-averse, tech-averse sector, it needs to be the opposite in today’s world. That’s an ongoing process, but you can’t just sit around for a year and keep things the same. Continually reminding people that we’re going to push, push, push. The kids are only here for three or seven years. They’ve got to have a dynamic, forward-moving school for all that time. That’s fun, but it’s hard. It’s much easier to be conventional.

What was the biggest undertaking during your first three years
To be honest, probably just keeping the school open. That was tough.

What, in terms of the new buildings, was the most difficult? I mean, there’s been a complete transformation of the physical plant.
All the renovations have been great, but I think the R+D Center was the most challenging and most exciting thing we’ve ever done. It was something that totally shapes and supports programs. It touches every kid and every faculty member. And it was a lot of work, a lot of planning, and it was really satisfying, but man, we worked our asses off for four years.

What keeps you up at night?
Staying ahead.

What bores you?
People who object to ideas based on logistics. Challenge me on vision, not the mundane details. Also, negative people and cynics bore me.

Who’s your personal idol?
I don’t believe in idols.

Okay, the person you admire the most.
This is going to sound like the Academy Awards or something, but I’m going to say my wife. Make sure you print that, by the way.

Beaver alum from your tenure who’s left the biggest mark in the world?
Well, you know, former staff writers at the Improper Bostonian. [Laughs] I’m not going to mention individual names, but we’ve got young people doing really important work in film and theater. We have alums working for NGOs, who are out there starting businesses, taking risks, alums who are making an impact. Most schools are really focused on making kids accomplished. We want to get kids to be interesting. It’s an important distinction, and I think it carries over to when they leave.

Thoughts on the college admissions scandal?
I think it’s easy to say that these are just a bunch of dumb, entitled, corrupt people, and they are a bunch of dumb, entitled, corrupt people, but I think it exposes a lot of the day-to-day inequities that go on in the whole college admissions process. It’s by no means a level playing field. It never has been. It favors certain people, people who can pay over people who can’t pay.

Worst confrontation you ever had with a parent?
I work pretty well with parents, but having to expel kids is an unfortunate reality. It’s probably the hardest thing I do. And I think really carefully and long and hard about it, but there have been a couple of incidents where it didn’t go well. I feel for the parents. I wouldn’t want to have to go through that, but there have been a couple of situations where it’s gotten pretty ugly.

The biggest challenge in dealing with faculty?
I had some run-ins with faculty, mostly regarding teacher autonomy. A lot of independent schools really pride themselves on teacher autonomy, and Beaver is about the student experience. While teachers have different personalities, or whatever, if we’re really going to be a school that focuses on using technology as an important tool, you have to do it right. Period. There were times when I had a lot of pushback on that. But we’re at a place now where the teachers get that. If you’re going to work here, this is how it’s going to go, and if you’re not on board, you’re not going to last.

Weirdest thing that ever happened during a school play?
Well, actually I remember when we just got onto the Internet. The Middle School musical was going on, and back then, the Green Room for Bradley Hall was in the library. This kid missed his cue to come onstage, and everyone was waiting, and it was getting awkward. Turns out, he was in the library, surfing the web.

Best senior prank ever?
I won’t tell you, because they’ll do it again this year.

How many games, performances, plays, etc. have you attended as Head of School?
If I had to guess, at least a thousand.

What do you think the one thing is that either students, parents or teachers would be most surprised to learn about you?
That I’m actually not an academic at all. That I had a difficult time in school.

How much of what you do boils down to being a psychiatrist?
A lot of it is maybe not being a psychiatrist, but being able to listen. I talk about empathy being an important skill. I also think you need to constantly remind yourself that everybody you work with doesn’t understand where you’re coming from. Different backgrounds and experiences form who we are, and you can never make assumptions until you really, really get to know people.

What do you hope your legacy is?
Building a mission and a vision for the school that has been really effective for all kinds of kids. The idea is to change kids’ lives, right? When I announced that I was leaving, and that I was exploring some ideas in the private sector, I got a really nice note from a teacher that said, “Congratulations, and good luck in the real world.” I said, “Wait. We are in the real world, aren’t we?”

Final question: if I’d told you when you were a teenager that someday you were going to, for decades, be the head of a very well-regarded school, what would you have said?
You’re out of your mind. I never in a million years would have believed I could end up in a place like this.