In 2017, Grace Cotter Regan became the first woman president of Boston College High School, a Jesuit, all-boys college preparatory school in Boston, Mass. Ms. Regan is not only the first woman to serve in the role in the school’s more than 150-year history, she is also just the second lay person. (Ms. Regan also serves on the board of directors of America Media.)
Ms. Regan earned undergraduate and graduate degrees from Boston College, then served as a post-collegiate volunteer with the Jesuit Volunteer Corps in Belize. She has worked in advancement and communications at high schools, universities, the Boston Public Library Foundation and the former New England Province of the Society of Jesus. All of this, along with her passion for the Jesuit philosophy of education, has helped her respond to the challenges of her role, including the threat of Covid-19 and reckoning with the school’s history of addressing questions of race.
This interview has been edited for clarity and length.
Being in an all-male environment, I am very mindful of being a strong role model, not only for women who might be aspiring to be in leadership at some point, but also for the boys.
How did you become the first woman president of BC High, and what has the experience been like?
I have a long history with the school. My dad was there for 50 years as a teacher, coach and guidance counselor—he was really an iconic figure at the school. I grew up there. I made every major life decision at BC High. Anything I ever decided, I met with my dad in the cafeteria to make the decision.
And then I went on to have my own life. I never expected to be a head of school. The lion’s share of my career has been in advancement, communications, brand, fundraising. When I was working for the New England Province of the Jesuits, I went to the provincial superior, Myles Sheehan, S.J., and said: “I think I want to lead a school. I’ve advanced all these leaders, and I think I know what I’m doing.” Within weeks, I had a few interviews, and I took a role at St. Mary’s in Lynn, Mass., which is a socioeconomically challenged area. The school was struggling, so I spent almost seven years turning it around. [The school] just opened a brand-new building, which I’m very happy to say. We created a whole new enrollment plan and offerings for academics.
I was contacted about the role at BC High in the summer of 2016, but I was really loving where I was. I was finishing up a $22 million campaign for St. Mary’s. I just didn’t feel the timing was right, so I pulled myself out of the search. They did not find a candidate in the spring of 2017, and they came back to me in June and asked if I would reconsider. Ultimately, I was selected. It was kind of serendipitous. My dad always used to tell me, “When God winks at you once, pay attention. But if he winks at you twice, you really have to pay attention.” I felt it was a vocational calling.
Being in an all-male environment, I am very mindful of being a strong role model, not only for women who might be aspiring to be in leadership at some point, but also for the boys. My principal, Adam Lewis, and I talk a lot about how difficult it is to be a young man in today’s culture. It’s important for us to help create and educate good men. One of the things I bring to that is I’m a mother of two boys. As a mom, I feel like I can really meet them where they are. I think for boys, especially teenage boys, sometimes all they need is someone just to ask, “How are you doing?”
I think for boys, especially teenage boys, sometimes all they need is someone just to ask, “How are you doing?”
Your community is working toward a cultural shift around the issue of race. Can you tell me what precipitated that and what it looks like now?
The spring of 2020 was challenging in many ways: Covid, virtual learning, the death of George Floyd and all that went along with it. An Instagram account [that highlighted the ways in which it was challenging to be a black student at BC High] was started, and a lot of the things written on the account were shocking and horrifying. We took the approach that this cannot happen at BC High. We had to have an institutional response from a justice perspective. We had to make sure our alumni, students, faculty and parents of color understood that we were standing with them and accompanying them on this journey. We hit things head on in terms of taking responsibility for our culture, with the understanding that our school should be inclusive and safe, and our students should have a strong experience. If we’re not doing that, then we need to address and remedy that. It needs to be a cultural shift.
Our board wanted to do an investigation, so they hired an outside consultant. They’ve been doing a study of our policies and procedures, looking at the Instagram account and giving anyone who wants it an opportunity to speak about their experience at BC High.
We’ve taken it upon ourselves internally to embark on a program that could really be meaningful for our school. We did implicit-bias training for our faculty and staff. We entered into a program called Courageous Conversations, which is a curriculum for creating cultural change. The premise is that the leadership has to own the protocol so we can bring that to the community. The board will participate in January. Our faculty and staff will do their second session in February. Then we’ll roll it out to the whole community. It will be a two-year commitment. This summer, we offered antiracism conversations over Zoom. I fielded about 200 phone calls personally. Our approach was about listening and sitting with the discomfort in order to think about our culture and how we are going to deal with it.
We’re also looking at our curriculum to make sure it meets the needs of our students, especially our young men of color.
Probably the best thing we’ve done is a student program to share our stories. In December, two of our young men of color spoke in front of our school in our gymnasium and Zoomed into the classrooms.
We had no choice but to pivot with Covid, and I think we have no choice but to pivot with antiracism.
How have you seen BC High’s responses to Covid-19 and to racism as related?
One thing I’m really proud of is that we have an emergency financial aid fund that helped many of our students to stay at BC High through the Covid pandemic; but we also are delivering hotspots and modems, as well as food cards, to students who are food insecure. You don’t know what people don’t have. As a Jesuit school, we want to make sure anyone on the margins is taken care of.
Some of our kids also live in tough areas, and they aren’t comfortable sharing their homes [onscreen during virtual learning]. We created backgrounds for students to use on Zoom so they could be creative and have fun and still engage in class with their cameras on without feeling uncomfortable with their background.
A number of our faculty and staff virtually attended the People of Color Conference with our principal this year. One of the presenters talked about schools’ responses to Covid: how we all pivoted, transitioned, stepped up. This presenter said: “What if this world took the same approach to antiracism we did with Covid? What if we made that commitment and said we are making this happen?”
We are going to be an antiracist school. We are going to have a community that is loving and embracing and safe for our students. Simple as that. We had no choice but to pivot with Covid, and I think we have no choice but to pivot with antiracism.
What do you think makes Jesuit education meaningful at the high school level?
For me, Jesuit education is about relationships. I go back to Pedro Arrupe [former Superior General of the Jesuits] coining the phrase “men for others,” which has become “men and women for others.” For us at BC High, it’s about creating good young people who are committed to justice and will be compassionate, ethical leaders.
When a young man graduates from BC High, he’ll be able to lean on the spirituality he learned here for the rest of his life. He’ll have a network of 15,000 alumni to support him. He will be a global citizen, having had the opportunity to travel through our programs and communicate with other schools around the world.
The most beautiful moment of the week for me is Wednesday morning, when our entire school stops to do the Examen. I could be in a board meeting, but I stop. It’s a transformational, action-oriented experience. That is what Jesuit education is about for me.
Jesuit School Spotlight is a new monthly feature focusing on Jesuit middle and secondary schools from around the country. It is underwritten in part by Jesuit high schools of the USA East Province of the Society of Jesus.
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