A Talk with Board Leadership: Keeping Boys at the Heart of the Conversation

By Chris Adams, Director of Communications and Marketing

In June, we sat down with two individuals whose love for Cardigan runs deep: outgoing Board Chair David Gregory P’18 and incoming Board Chair George “Jory” Macomber P’12. Both are former Cardigan parents who know firsthand the transformative power of the Cardigan experience, and both have played important roles in guiding our school.

David Gregory, the 13th chair of the board, has led with integrity, steadiness, and a deep appreciation for our mission. Under his leadership, Cardigan has continued to grow in both strength and vision. Jory Macomber brings a lifetime of experience in independent and boarding school education to the role and was a key contributor to the development of The Strategic Plan for Cardigan 2032.

We discussed the joys—and challenges—of board leadership, as well as the strategic priorities they believe will be most important over the next four years. Their perspectives reflect not only their professional wisdom but also their personal connection to Cardigan as past parents, always putting the boys at the center of the conversation.

Chris Adams: When the opportunity to serve on the board arose, were you eager to say yes?

Jory Macomber: The first connection for me was [Head of School] Chris Day P’12,’13. We had worked together for a long time, our kids had attended Cardigan together, and I think he was looking for someone to join the board who had boarding school experience as an educator. Before I was on the board, I helped to facilitate a strategic planning retreat in 2017, and the board members who were there were really interesting and fun people, so that was also a draw for me.

David Gregory: Well, I don’t know that I was eager at the time. I hadn’t served on any boards in the nonprofit world, so I thought it would be a unique opportunity for me to give back and to learn. My own professional background had not been as collegial or as mission-focused. And I certainly felt a connection to the school because Max ’18 had such a strong first year. I thought I had the voice of a parent who had been going through some things, and who could add to the discussion and advocate for other students like him.
 

I’m really committed to the idea of opening the doors of Cardigan to as many people as possible. This is such a unique and wonderful educational experience. I want it to be accessible. David Gregory P’18

CA: What do you look forward to when you visit campus?

DG: I like being around the faculty, the teachers, and seeing the boys. The people, the place, and what goes on there—that feels special for me. Cardigan was a source of joy for my son, so I always like to be close to the source of that joy.

JM: My biggest connection is with the staff as well. I’ve been a boarding school employee most of my life, so I enjoy meeting with and working with them; I feel I can add some perspective from my experience that may be helpful.

CA: Do you have a favorite place on campus?

DG: I like coming around the corner of Clark-Morgan and seeing the field and a little bit of the water, and then seeing Mt. Cardigan. On a nice day, it’s pretty spectacular and peaceful.

JM: The baseball field. I’ve always been a baseball coach, so I’ll wander out and put my feet in the grass. You can see the view of Mt. Cardigan from there.

CA: You both have talked about why your sons were successful here. If you were to boil it down to one thing, what is Cardigan’s greatest strength?

DG: Slogans matter, and our slogan of “We’re going to know your boy and love your boy” is all you need to know. It’s really that simple.

JM: That’s a great answer, David. For me, it’s being a close-knit community. When you see the laughs and the hugs and the tears among the boys and faculty—that’s real.

DG: I was able to go on the Sunset Climb the year I spoke at Commencement. Everything I needed to know, I heard on that mountaintop—the boys in tears, thanking each other and poised enough to thank the adults in their lives. I saw middle school boys find their voices on that mountaintop and say, “This place has mattered.”

JM: As a person who taught a lot of Cardigan alumni at Holderness School, I’d also say that they have their act together academically. They have executive functioning. They get their homework done. They stay organized. They know how to ask for help. They know how to contribute to class.
 

We’re creating a place where we can hire, develop, and retain the best faculty who are leaders in middle school education. George “Jory” Macomber P’12

CA: David used the word “joy” earlier. Is there anything in particular about board service that brings you joy?

JM: It’s probably the other way around for me. I try to say stuff that makes people smile or laugh, so in a sense, I try to bring joy to the group. This is kind of geeky, but when people laugh together, it means that they are on the same wavelength—they have to kind of understand what is funny. I think they call it emotional congruence.

DG: This is a really good board, so it attracts good people, and there’s a good culture. So for me, it was a joyful experience getting to learn from other people and feel like I was part of the team.

CA: Is there a priority in Cardigan’s strategic plan that’s particularly important to you?

DG: I’m really committed to the idea of opening the doors of Cardigan to as many people as possible. This is such a unique and wonderful educational experience. I want it to be accessible. It’s important that we’re a place that is diverse, that’s fair, that cultivates a sense of belonging, and that is accessible to more and more people. Our commitment to raising our endowment and the amount of financial aid that is available is the most important thing to me.

JM: The strategic plan starts with people—the faculty and staff. We’re creating a place where we can hire, develop, and retain the best faculty who are leaders in middle school education. But as David said, moving forward with these initiatives is about raising endowment. Raising funds for endowment before facilities is actually—I don’t know if the right word is “radical,” maybe “aggressive” is a better word—but to think that way is really important.

CA: What are the biggest challenges facing Cardigan?

DG: I would focus on a couple. We’re in a time of political volatility, which potentially has an impact on our international students. With about 40% of our student body being international, geopolitics matters. Then, the challenges presented by artificial intelligence, social media, and the cultural influences on adolescent boys will require our best skills to adapt to how boys learn and how they can be supported.

JM: I am concerned about the expense of education. The pool of families that can afford Cardigan is shrinking. A boarding school in New Hampshire was forced to close [last spring], and I’ve recently read about colleges struggling to fill incoming classes. As David mentioned, international students may face challenges. That’s why we’ve made raising endowment for financial aid a priority. Also, how are we going to use AI as a tool at Cardigan Mountain School? I don’t have the answer; I just know that it’s something we have to figure out going forward.

CA: David, any last thoughts to share before your term concludes?

DG: It’s been such an honor to serve. I’ve gotten much more out of it than I gave—from board members, from the faculty, from the entire team of people who taught me things. One of my lasting memories will be speaking with parents about experiences that touched their hearts. I always say that you know the mark of a good school: Is it the kind of place that makes you cry? And you know Cardigan has always made me cry tears of joy and gratitude because it’s a special place.

CA: Jory, what are some of your thoughts as your term is about to begin?

JM: With David, he has a massive commitment to equity and accessibility. It’s at the forefront of what we do, and it will remain there. I’m going to add another angle. Chris Day has been our head of school for nine years. I’m going to ask him, “What do you want your legacy to be?” My job is to help him answer that question, and then work on it—together.

This article was originally published in the summer 2025 issue of the Cardigan Chronicle