Feature: A Conversation with Kathy Giles

School prepares to welcome Fourteenth Rector

Eliza Griswold ’91 and Anne Fulenwider ’90

On July 1, 2019, Kathleen Carroll “Kathy” Giles will become the Fourteenth Rector of St. Paul’s School. The SPS Board of Trustees unanimously approved her appointment last summer. Kathy brings in-depth experience and appreciation for the merits of boarding school life to her role as Rector. Since 2003, she has served as head of school at the Middlesex School in Concord, Mass. Prior to that, from 1990 to 2003, she worked at the Groton School in a variety of roles, including dean of academic affairs, college adviser, English teacher, and coach.

Kathy holds her M.Ed. from the Harvard Graduate School of Education, a J.D. from Harvard Law School, and her A.B. in English and American literature and languages from Harvard. She played hockey for the Crimson and, as a senior, broke Harvard’s single-season scoring record at the time with 50 points on 23 goals and 27 assists. Kathy has been married to her husband, Ralph Giles, since 1985. They have three grown children, Kaitlyn, Daniel, and Eileen, and three dogs, Breezy, Tucker, and Lucy.

Kathy Giles sat down with Alumni Horae Advisory Board members Eliza Griswold ’91 and Anne Fulenwider ’90 for a conversation about her life in education, her leadership style, and her hopes for St. Paul’s School in the future. Additional thoughts incorporated into this conversation were shared by Kathy in her February Chapel talk to SPS students.

Alumni Horae: Tell us a bit about yourself and your arrival here as Fourteenth Rector.

Kathy and Ralph Giles (c.) with son-in-law Matt (l.), daughter Kaitlyn, daughter Eileen, and son Dan.

Kathy Giles: [My parents] moved us when we were small to Portland Maine, and we grew up there and loved it. I graduated from Portland High School, went to Harvard, and did the student-athlete thing there as a hockey player. I loved music but really loved athletics, too. After I graduated from college, I had an acceptance to law school but knew I wanted a year off. While I was at Harvard playing on the women’s ice hockey team, periodically we would play the prep school teams. During my senior year, we scrimmaged the Groton girls varsity. My coach, John Dooley, introduced me to Groton’s coaches and later encouraged me to think about applying for a job at Groton. I ended up at Groton on a one-year internship in the English Department and coaching field hockey, ice hockey, and crew. I met this awesome young math teacher, Ralph, and we ended up getting married during the fall of my first year in law school. We lived at Groton with 12 senior boys and 39 ninth grade boys while I was in law school. I continued coaching ice hockey and, after that, I clerked for the [Honorable Vincent McKusick of the Supreme Judicial Court for the State of Maine]. By this time, we had two small children, and I couldn’t figure out how to be the kind of parent I wanted to be and a lawyer in Boston.

We went back to Groton School, and Ralph became the athletic director, and I jumped into the college office. We had really wonderful opportunities under Bill Polk, who’s just a legend in the school world. We had a third child, and our eldest decided that, instead of going to Groton, she wanted to go to Middlesex. So she went, we sent the tuition check, and about a week later the Search Committee called [about the head of school job]. We had already done the due diligence on the school, and we followed her to Middlesex – it’s been 16 terrific years there.

We have three children. Our eldest, who got married a couple of years ago, is with Excel Academy in Boston. Our son is a playwright in Brooklyn, and he has an awesome boyfriend, who is a journalist. Our youngest works for National Cathedral School. She’s getting married three days before we move in June. I made my first trip to St. Paul’s as the JV girls ice hockey coach for Groton School in the winter of 1985. Perhaps a more memorable visit, three years later, was when my then-six-month-old daughter and I stayed over in Scudder, while my good friend and assistant coach stayed with our varsity girls hockey team in the old wrestling room while we played in the December hockey tournament. My husband, Ralph, will never forget his first visit to St. Paul’s in the fall of 1971 when, as a freshman playing for the Groton boys JV soccer team, he suffered what he to this day remembers as his worst athletic defeat ever – high school and college, playing and coaching – a 6-0 loss on that soccer field near the visitors’ parking lot.

AH: What is it about this School that draws you here?

KG: I believe that all organizations benefit from new energy and new vision and that the timing is right for Middlesex to benefit from a change. Ralph and I are thrilled to be coming to St. Paul’s, as we have long admired the people that make this school so great – because the heart and soul of any school, no matter how beautiful the grounds or the buildings, are its people. We’re very straightforward. I actually really love school and work a lot. Ralph and I are career school people, and we love kids, and we’ve spent our entire professional lives in these boarding schools, and we believe in them. So, we’re excited to come. Ralph will retire. He’s been the head of the Math Department at the Fenn School for the past 14 years.

AH: What is your aspiration for St. Paul’s? What do you envision for the future?

KG: I’ve been asked a lot already about what my vision is for St. Paul’s, and while I hate to disappoint people, there’s no mystery – it’s the same as everyone’s here. We want this school to be the best St. Paul’s School that it can be, the best that we can make it. The best days of this great school are out in front of it, and none of us has that vision yet, but we share the pillars of that vision. We want students to be safe, challenged, inspired, and transformed by teachers and by each other as they do the work of learning and growing up.

AH: St. Paul’s is 100 percent residential. How do you see the role of the residential community now?

KG: There was an article in the Times [recently]. I think it was called “Bad News, the Helicopter Parents are Winning.” And the gist of this article is that parents who don’t let their kids hang out on screens the whole time, who trot them around to lessons and games and practices, see more successful kids. That’s the boarding school recipe, right? A lot of schools like to talk about their whole-child approach. But the residential school is a uniquely whole-child approach place – school values don’t really mean anything until the kids start reflecting them in their decisions and in the ways they treat others. The fully residential piece is intriguing to us because both of our schools have had day students, so we are eager to see how the fully residential community manages its intensity.

And for those schools, that’s great. It’s a little fresh air coming in, but it also is a potential opt-out. And this community doesn’t suffer from that. These kids are going to have a set of interpersonal skills and decision-making skills that will set them apart. Boarding schools have always accelerated able kids’ personal growth. But I think that, going forward, kids at our schools are going to have the enormous advantage of knowing how to work with people, how to communicate with people, how to build relationships that work for them at critical times. Also, all the data that’s coming out about kids and screens, it’s just not good news for interpersonal skills, leadership, ethical growth, and development. In a boarding school environment, they have to put down their screens. We’re going to try to make real life more compelling than screen life. I think that’s our job.

AH: We’re in a radical new society, where there’s a demand from young people for all forms of equality. How do you see the role of educators in creating this new society?

KG: That’s how we want to live. Schools are microcosms. Schools are where kids learn to set their frames of reference. Families are big places for that as well, and ideally, schools and families work together that way. My experience is that families self-select on that process. They’ll look for a school where the values align, and the practices align. Our job as educators is to help kids calibrate their frames of reference and their standards.

AH: What kind of standards?

KG: For example, when I hire people, I hire expertise where we need it, and we don’t always need Ph.D.s. Sometimes we need emotional geniuses, right? Secondly, we hire people who want to work with 13-to-19-year-olds, because not everybody likes teenagers. We need that to survive in a boarding school. Third, we hire people who have the right frame of reference and the right standards. They’re people who want to solve problems. You know, there’s a little bit of hurting at first? When you’re 14, and you have Saturday classes, and chemistry is at 8:30 a.m., our job is to flip that around to say, ‘Don’t you feel smart? Don’t you feel mighty?’ And there’s a confidence piece for youngsters that comes out of that. And I think that’s how you help kids stretch what they think is possible in their lives.

AH: What was your biggest challenge at Middlesex and what is something you’re most proud of from your time there?

KG: Middlesex suffered a little bit from feeling as if it wasn’t as strong as some of the schools around it. My job was helping to develop a sense of institutional identity. The shorthand version of the school’s mission is to find the promise. I think it’s been energizing the community around how we do that. We’ve done a lot of work with the endowment and with admissions. We’ve raised the profile of the school, and we also have built a community life and human development program. We’ve adopted the positive youth development work from the Stanford Center on Adolescence. It’s a really simple equation of high-energy, talented kids in an environment rich in invitations, with great adult coaching.

AH: St. Paul’s is quite rooted in the Episcopal church. How do you see the church, or spirituality, as part of the curriculum?

KG: That’s an interesting question because right now there is a conversation on campus about what is the School’s Episcopal identity. One of the very good questions [Interim Rector] Amy Richards is asking is: Which comes first, the identity and the affiliation or the mission? The School in 2020 has to be careful that everybody not only feels invited in but feels equally valued by the School and belonging. So I think the Episcopal identity has to be about the values of the School and not as much the forms of practice. The question we have is how do you bring the best of that into a context in which you have a truly inclusive and equitable community? I think there’s a desire to renew the understanding of the values and acknowledge that they’ve always been the School’s values. So a shift to the right in terms of dogma is not the right thing from my perspective right now, but kind of a recommitment to the good values is just right.

AH: What attracts you about the job and coming to the School and what are your priorities when you get there?

KG: The interesting thing about this is that I actually told a lot of people multiple times that I really wasn’t the right person for this job. Archie Cox just is a hard man to say no to. At Middlesex, we’ve just finished a $239 million campaign, and we have made substantial progress toward the next campaign. We’ve just opened up a visual arts center, a performing arts center, a music center. We’ve got these curricular initiatives. Admissions is great and the endowment is at an all-time high. Everything is good. For me it’s year 16, and I’m 56 years old, and I don’t really want to get to 20 years at age 60. I think 20 years is a long time for an organization to have a leader these days. So, I’ve been thinking about this for a while, and there are only a couple of schools that would interest me. With this one, I think I bring some building skills that can be helpful to the School. It has remarkable resources. And yet it’s right up against all the challenges boarding schools are up against.

It’s a rural place. It’s a wonderful place with a terrific history, with a set of interesting challenges right now. I actually feel like I’ve got a skill set that’s been getting ready for this, so now maybe I can make a good contribution at a time when I think the School can use it.

AH: What do you see as the biggest challenges facing St. Paul’s now? And what are your thoughts on addressing them?

KG: When I talked to the faculty [recently], I said, ‘I don’t want to disappoint anybody, but when people ask me what my vision is, it’s not very surprising, and it’s what everybody shares.’ [Again,] we have to believe that the School’s best days are out in front of it. It’s not going to be the version it was 10 years ago or 30 years ago or 50 years ago. It’s in a different world, and it’s in a different place. But it has everything it needs to do that. My job is going to be to remind everybody of what the strengths are and galvanize good energy around that. That’s something I hope the entire constituency can get excited about.

AH: What do you see as the School’s distinctive strengths?

KG: [St. Paul’s] needs to continue to produce leaders because that’s what society needs, from all of our schools. Because kids come to us, they accelerate their growth. They not only have outstanding intellectual opportunities but they are supposed to grow in terms of their ethical, spiritual, moral fiber so that when they leave us they’re ahead and they can go out and they can be the leaders in their college communities and their larger communities. I think the School has a leg up on that because that’s always been part of its calling. I think the fully residential community is a strength. And I think the stellar academic piece and this unparalleled ability to go out and get great kids are strengths.

AH: We’ve been hearing and listening to a lot of issues around race at St. Paul’s. Have you done any thinking about that?

KG: Yes. We’re all working with it. In independent schools, we’re all conscious of race in new ways, and that consciousness is important and good for all of us. Race and its role in identity formation are very powerful factors in young people’s lives and in school communities. And in developing kids’ frames of reference, we talk a lot about empathy. For each and all of us, understanding race as a factor in one’s relationships with others requires empathy. You have to choose to want to understand the experience of someone else, particularly if it is not your own. When we do leadership work with kids, the definition of leadership that we use is more akin to ethical citizenship. You learn to see yourself in the context of other people, you learn to empathize with and value their experience, you learn to see their needs, and you learn to choose to act to meet those needs. You choose to do the good for the community. I think one of the big issues in helping each other understand the ways race shapes and affects our lives is that we have to help kids want to see and understand the experiences of other people, particularly people from backgrounds and belief systems that are different from their own. That work is hard because it can become very emotional when guilt or anger or a range of other reactions attach to that understanding. So it’s ongoing work in a number of important ways, as we see in the ongoing conversations about race throughout our society.

With kids, that work around awareness of the experience and needs of others needs to be constant, and it starts with the premise that our school aspires to be an equitable, inclusive community and refuses to fail in this goal. The hardest thing about being a student at St. Paul’s should be getting in, right? After you get in, you’re in – and you belong.  The School may challenge you in a number of ways – chemistry might be hard, performing might be hard, athletic training might be hard – but feeling as if one is not just invited in but welcome should not be hard. There is no question that everyone belongs to the community on equal footing, with both equal opportunity and equal responsibility. And I think it’s our job to foster and encourage and insist on that dynamic. 

AH: Given your legal background, do you see yourself as in a good position to work with the New Hampshire Attorney General?

KG: There’s a piece of my training that helps me not be conflict-averse. And I think a lot of people go to schools because they’re conflict-averse. I don’t love conflict at all, but I am not conflict-averse. The laws around the care and protection of children are super-important – and they’re not a matter of opinion. I think with the AG, there has been a complicated conversation going on for years now. Archie Cox, to his enormous credit, has spent the better part of the last 18 months trying to straighten this out. So, one of my priorities is making sure that we have a very good relationship with the compliance overseer, who is, I think, a terrific add. One of the tricks here is going to be to rebuild that trust because the AG, the police, they just want to do their jobs. And it’s easier coming in as somebody who is new to these issues.

AH: What question haven’t we asked you that you’d like the chance to answer?

KG: The interesting thing is that Amy and I are the first people to come into the Rector’s position with head-of-school experience [since Tenth Rector David Hicks]. She brought that up the other day, and that’s going to be a different feel for the School. As I said to Archie Cox, I don’t belong to any club. I’m a public school kid from Maine. Yes, I have three Harvard degrees, but that’s been about my professional and personal training. It hasn’t been about cashing in on anything. So I feel like I’m a professional coming in to do work that I really love to do in a place that’s been a little insular.

There are just ways you help kids be good. They need to have fun, but it needs to be fair, healthy fun. They do not need to have too much pressure on them but they need to work hard. That’s why you come, right? You come to learn and grow. So I think there will be a sense of cultural shift. I think there might even be a sense of loss. I think the School has felt some of that in the past couple of years. Just having a female Rector is a significant cultural shift that has already been felt under Amy’s excellent leadership. The current School – current faculty, staff, students, trustees, parents – have been dealing with the effects of a venerable, human institution beginning to address its shortcomings and mistakes, even though the current School community personally had no part in them. There have been sudden transitions in leadership as well as changes in the faculty and staff. Schools are like families or churches – change usually involves a sense of loss, and whether it is a change in the way the organization sees itself or an actual change involving people, people who are beloved, there is a sense of loss. That’s inevitable, but the organization is full of good people doing great work, ready to continue that work and move forward.

AH: Just one question for fun. What’s something that everyone is going to be surprised to hear about you? Something not in your bio?

KG: We do dogs at my house. We have three – a spaniel, Breezy. She’s well-known to all of the kids because she’s the star of the show. And then we have a dumpster dog from North Carolina, a German Shepherd, Tucker. And then our huge, 11-year-old, OCD, bossy, black Lab, who can’t get her toes wet. And then we have two grand-bulldogs. One’s an English bulldog, and one’s a Frenchie. We do open houses, and the kids will come over, and the dogs will come out, down on the floor with a lot of puppy love. So we’ll do some of that.

AH: What would you want today’s students to know?

KG: As I said to them in February when I was introduced in Chapel, [the students] came to St. Paul’s to become educated in that classical sense of that verb ‘educate,’ drawing forward what is best. Every day they work at growing up well and learning the skills, content, values, and habits to build the lives they want to lead. Their job, now, might be to get their essay or lab report or problem set done for tomorrow (hopefully not for later today?), but while they’re doing that, they’re also figuring out how to do something new and hard, well. That’s really what we do – we learn to do hard things well, whether it’s physics or racing or dancing or being a trustworthy person of high integrity. If they learn to do hard things well now, they change what they think might be possible as they take on the next hard thing or the next big challenge or the next problem that no one seems to think can ever be resolved. One of the most exciting parts of this work, for me, is knowing that, even as students stretch and grow now, they will leave here ready to make the world better. It needs to be better; it needs them. The work we do here can indeed change the world for the better, and that’s all of our jobs. It’s pretty big fun, actually, in that school-person kind of way. I’m in this business because I love the life, I love the work, and I believe in both.