A Conversation with Future Head of Schools Jake Guadnola

Jake Guadnola ’90MS, who will succeed Christian Sullivan as Head of Schools on July 1, reflects on his long history at Annie Wright Schools, how he plans to lead, and what he is excited about for the future.

Listen to the full conversation with Communications Director Lisa Isenman at www.aw.org/guadnola.

LI: Tell me about your family history at Annie Wright.

JG: My family history begins back in the early eighties. My mom was hired to be director of communications under Bob Klarsch. I was at Washington Hoyt public school up on Proctor and 26th. And my mom comes to school one day—she hadn’t told me about this—and says, ‘I need to see Jake,’ and she takes me out and she says, ‘You’re going to go to a new school and we’re going to go visit it.’

She drives me over here. I was still pretty little at that point in time and I hadn’t ever remembered seeing Annie Wright. And I walk up and it’s just this…it’s a castle, right? I mean, I can’t even imagine that this place is a school. I’m suddenly scared to death. I get walked inside and I get plunked into Jean Schneider’s second grade class, and what I didn’t realize at the time is sitting in that classroom were four or five boys who would end up being very good friends of mine for a long time. We would have some really tremendous, impactful, transformative experiences as we worked our way through Annie Wright. So my history began then. I then had Miss Reeves for third grade, Mr B. [Jan Buennagel] for fourth grade, Jane Robinson for fifth grade.

Then Bob Klarsch approached my mom and said, ‘We’re really thinking about having boys in the Middle School and we think this might be a good class to do it with.’ We were generally good students, and I think we were a group that they were excited to keep. And so they did. They opened up the doors to sixth grade, and we went.

Through that Middle School experience we got to feel, I think, in some ways similar to the way the boys in the current Upper School for Boys feel. We were that first group to make our way through, and it was exciting, and it had that pioneering feel, and yet you still felt like you were part of this bigger, longer history. It was a profound experience for us, and for me in particular.

I came back in the late 1990s/early 2000s in different capacities. Susan Bauska for no reason that I can understand decided to hire me to be the college counseling director. It was the 2000–2001 school year. I started in that role, and I’ve been here ever since. My wife, Stacey, got a job as a dorm parent here, before joining the admissions office, and then development. We started a family. Gus [Grade 5] and Luke [Grade 3] have been here since Preschool, since they were three years old. Their whole lives have been associated with Annie Wright. It’s fun to see them feel this place the way I felt it as a kid, to the point that Jan Buennagel has now taught me, Gus and Luke. So to say that we are all in as a family would be an understatement. This IS my family.

LI: I know you’re in touch with some friends from those days. How did they react when they heard the news of your new position?

JG: They were generally very excited for me. I think they feel the same way about Annie Wright. The place becomes who you are, right? And so for them, the thought of me being in this role is both hilarious and wonderful. And I think, to them, perfect, in the sense that how great that someone who knows and cares so much about the school can be in this role. They tease me that I’ve never left—it’s time to graduate and move on. We get a good chuckle out of that, but I think they’re all really excited. I think they feel, here’s somebody who really knows and cares about the place, and Annie Wright really is one of those things that we pivot and orbit around.

LI: You must have a lot of feelings about your new position. Will you talk about some of those?

JG: I couldn’t be more excited, and the excitement stems from what I attribute to the deep heavy lifting that Christian and the Board have done in the last ten years that has been transformative. We’ve moved into this space where I think there is a lot of positive momentum. I’m really excited to keep that momentum going.

On the flip side of that, there is now an expectation. So I’m excited about it, but I also realize there’s a lot of work to do. I think of how my grandparents were. They were depression era folk. I always remember my grandfather was kind of weird about money, because they remembered a time when it was bad. And oddly, I sort of feel that way. I remember that at Annie Wright. I worked here for a decade when it was tough. I’m actually really glad that I had that experience, because I think if I were to come into Annie Wright now, without that experience, I might come in and I might be tempted towards complacency. We’re not going to be complacent; we’re going to keep driving forward. We’re going to be the best school that we possibly can be, and we’re going to be student-centered and financially well-run.

Gus, Jake, Stacey and Luke Guadnola

with Upper School students

with Mr. B.

So am I excited about this? Yes. And do I realize that there’s a challenge in there and am I motivated by it? Absolutely.

LI: You and many of the adults in the building have been thinking about this transition of the Head of Schools. But I think the transition that many students are thinking about is your role out of Director of Upper School for Girls, which is very impactful. How do you feel about that, and what are you sad to leave?

JG: I think the challenge you bring up is how can I make sure that this transition is as seamless as possible. The first thing is to get a good person in place, and I am so thrilled that Eireann Corrigan is joining the ranks as Director of Upper School for Girls. From the minute we spoke with her, she did nothing but radiate exactly what we believe in. I think my challenge is how can I remain supportive and involved, but also be removed.

If you asked me the things I’m going to miss, the truth is everything. I’m going to miss sitting in that office, and class is getting out, and kids tumbling by and saying, hi. Terah Gruber walking by with a silly joke and Cady Hale coming in just to talk.

You get a whole bunch of kids and faculty who you spend so much time with, and you really feel like you know them. One of the things I’ve realized about

administration is every level that you go up, you get more and more removed from kids. As Head of Schools, my job is to make sure that the faculty have great relationships with kids, not for me to have great relationships with kids. I still want to, but that’s not my job. My job is to get a team of people who care and deliver really well on that mission-centered initiative.

(far right) in Middle School

So I think I can do that. I’m excited to do it, but I will look longingly down the hall at the Upper School for Girls. I mean, that place is just so fundamental to who I am.

LI: What are some of the things that you’re particularly proud of having achieved in your role as Director of Upper School for Girls?

JG: I love our (s)Electives [after-school deep-dive activities] program. I love the way our schedule has changed over the years. I love the late start. I love the curricular decisions that we’ve made. I love the way we’ve worked in terms of building out things like college week. I can point to those things, but those are all born from a way of approaching the work that we do. It’s not that one thing. It wasn’t like a new light bulb went off. It’s that we try to constantly ask ourselves, how do we do this better? What are the problems that we’re seeing? How can we improve student engagement and performance and satisfaction? I love the way we function as a faculty. I love the way we function as an admin team. It has been amazingly generative.

The culture that the kids have is astounding. I don’t want to say I’m proud of this, because I don’t know exactly what hand I had in it. Instead, I think this is more that the kids themselves built a culture of communal expectation of each other, one that is wrapped in empathy. And so suddenly everybody gets excited about investing, but not just in their schoolwork. When we say do the work, that means coming to Inkwell [journalism (s)Elective] and coming up with a podcast idea and executing on that. It’s voluntary; there’s no credit given. They’re just kids who are doing these things because they want to, and once they got that ball rolling, it really picked up steam. So now these kids are everywhere doing everything on their own initiative, and that’s something I’m extremely proud of, if that’s the right way to put it. It inspires me to see the way the kids engage their daily lives, and that was very much a collective effort.

LI: How would you describe your leadership style?

JG: I think anytime someone answers this it is probably aspirational. I try to value process. I try to listen and I try to understand problems, so if there is an issue, I want to understand all of it. And then when we try to solve it, I think we need all the voices of the stakeholders in

The challenge that I have is I often get going with ideas, and I can run really fast. And so sometimes I have to really try to slow myself down and say, okay, let’s make sure everyone is involved and aware. When I do that, I feel like I’m a very effective leader, and when I get going too fast, sometimes I could be right, but sometimes I’m not. So I try to listen. I try to be empathetic. I try to lead in a way that is people centered.

LI: Hopefully you’re going to be here for a long time. What are you looking forward to doing and where do you see Annie Wright going under your leadership?

JG: I have pondered that a lot, as you can imagine. The school is in such a wonderful

our culture. We love the culture that we have. We know that invariably there will be slight modifications here and there, but I would love for Annie Wright in ten years to be a place where we had a clear articulation of what coordinate was and where we had been able to maintain the culture that we currently have.

At the same time, we’re going to have questions about the Lower School and the Middle School. We are already hitting capacity there, so we have to figure out how we can have more applicants than we have space and how can we work to craft a class that is the type of class that we’re really excited about moving through this school.

That will be a tremendous opportunity, but that is not as easy as it sounds. It’s actually really complicated and exciting work. We’ve got an athletics program that is running wild right now and in a positive way. What about the arts? I think we

more focused externally, especially reaching out to our alumni community. Can you talk about what your hopes and plans are for connecting with them?

JG: I believe there are a lot of people out there who had the same sort of experience going through Annie Wright that I did. There were amazing adults who cared deeply about me and invested themselves; you look at [Diane] Soucey and [Jim] Timson; I mean, they invested a lifetime, multiple lifetimes in this institution. And those people matter. They mattered to me. I think they matter to a lot of alums. Likewise the friendships that were born. I think there are so many alums that are still in contact with one another, and again, Annie Wright is the thing that they orbit around.

I think we can really try to reignite that engagement. For a lot of reasons, the last handful of years for some folks has been complicated. The boys’ school was not

To say that we are all in as a family would be an understatement. This IS my family.

place. Christian and I were together the other day, and we were asked, ‘If you could describe the school in one word, what would you say?’ His response to that question was ‘ambitious.’ And my response to that question was ‘ready.’ And I think it’s interesting when I look at where the school has come from historically and where we are now, we are in such a good place, but we have things that we have to do.

We can remain firmly committed to the single gender experience in the classroom, and we can begin to understand how socially and in some extracurricular spaces we can have the boys and girls together, so that I truly believe they can get the best of both worlds. How do we do that? What is the speed at which we do that? Those are going to be amazingly important decisions for the school, because we don’t want to change have a strong arts program now, but even though it’s strong, it doesn’t feel to be on the same level as the sports program. So how do we get it there?

We’ve also got important work around diversity, equity and inclusion. We have to understand who we want to be. We have to work collectively as a community to understand where our holes are. I think it’s really important that we hear from our constituencies. And so in ten years, if we could be a space where we have collectively defined and understood what strong DEI culture and community looked like at Annie Wright and we had the metrics to tell us whether or not we were achieving that, that would be profound.

something that some alums were really excited about, although there were many who were, and I think that’s okay, and I can understand that. If there are alums who feel, ‘That’s it for me and Annie Wright,’ that’s okay. But I want to make sure that anyone who is open to re-engaging that commitment or that relationship with the school has the opportunity to do so. We will be putting together opportunities and programs so that we can re-engage with those people.

I’m so excited to see where that all goes in the future. I think there’s going to be great opportunity, and I’m very much looking forward to being a part of that reconnection if it is a reconnection for some folks or to deepen the connection that already exists for those who are still in a relationship with the school.