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Heather Sugrue Is the New Academic Dean

Heather Sugrue Is the New Academic Dean

Heather Sugrue, who this past summer became the new Upper School academic dean, has witnessed two decades of Milton Academy as a math teacher, a house head, and most recently, the math department chair. She replaces Jackie Bonenfant, whose role has transitioned to dean of academic initiatives. In a recent interview, Heather discussed the joy of teaching math, her excitement about her new position, and what makes Milton students so special.

What was it about the position of academic dean that interested you?

As math department chair, I found it rewarding to use my math knowledge to collaborate with the adult community here. I really enjoyed that. I also felt that I was creating some new habits as department chair, as opposed to following expectations or guidelines. There were challenges and exciting parts. That made me think a lot about how we can make other department chairs feel supported as they step into their roles, which was a big draw to this new position.

The other piece, and the thing that’s kept me at Milton since my arrival in 2001, is the students, because they’re amazing, unique, and interesting in so many different ways. I have loved the opportunities to get to know my advisees, the students in the dorms and in my classes, but this new position gives me the opportunity to get to know even more students while we’re helping them to navigate this place.

What does the academic dean do?

It changes from day to day. This office oversees attendance, and I work closely with the class deans to make sure we’re supporting students. I’m at the helm, but a lot of other people are involved. Another part is making sure faculty know what is expected and helping new members. I work closely with the other deans and the Upper School principal, and I’m involved if there are academic integrity violations and discipline committee issues, as we help students in those moments where there’s been a misstep.

I work closely with Kate Collins, the director of academic support in the Academic Skills Center. If a student is struggling, we’ll meet together with their teachers to make sure we’re all on the same page. This helps, because if one person sees something a little off, they won’t dismiss it because they’ll know we’re seeing it across that student’s classes. I talk to students one-on-one about how things are going, and try to help them if they hit a bump in the road.

What are some of the ways the math department has changed since you started at Milton?

A number of teachers were hired while I was chair, and it’s been exciting to see how great they’ve all been and how much they enjoy Milton. I also did and continue to do a lot of close work with Chris Hales in computer science. It’s his love but something I’m interested in too. That partnership led us to create this mini-unit exposure to programming that’s in all the geometry courses, which has been a great addition.

Math can be intimidating for some people. How do you make it more accessible and exciting?

A lot of fear about math is from people being told they are not good at it, either explicitly or implicitly, for a long time. It begins in elementary school, where acquiring math skills requires being a fast processor. If you do take more time, there’s an assumption made that you’re not getting it or it’s not making sense. Things start getting hard in fourth and fifth grade, maybe even in third. I am in awe of elementary school teachers who are teaching every subject in a classroom with the same group all day. That’s such a gift and such a challenge. There are a lot of people who say that they’re scared of math, or bad at math. It is not unlikely that there are elementary teachers who put themselves in that place. It’s hard to share the joy of math if you’re actually a little scared of it yourself.

But we can all find joy in math. That’s the culture we’re working to build at Milton. We may not all choose to be mathematicians, and that’s fine. In my classes, I find ways to invite more students into the joy that is “playing with math.” I love low-floor, high-ceiling problems that everyone feels like they can at least try, and where there really is no limit to where you can go with a solution. I also try hard to ask questions to which I don’t already know the answer, and focus on listening to my students.

Was there someone or something that inspired you to become a teacher?

My dad was a math teacher, so it was definitely on my radar. I grew up at a school that’s in some ways similar to Milton: Westtown School, in Pennsylvania, another K–12 school with boarding and day students. I always liked math, so it wasn’t anything new or surprising that I might study it in college, but I wasn’t planning to be a teacher. I majored in math and minored in French. When I came out of school, I started working at a French library in Boston, which was fun, but also a little boring on a day-to-day basis. The first day that I looked for a new job, I saw an opening for a calculus teacher at St. Paul’s School, in New Hampshire. I interviewed, and that’s where I started teaching.

What is the biggest challenge you’ve faced as a teacher?

I’m a very different teacher now than I was when I started, and even than six or seven years ago. The thing that makes teaching challenging is also what makes it so much fun: You can always do it better, and you have do-over moments every year, or even every day. I’m always planning, thinking about what we’re going to do, and knowing that I’m probably going to change the plan because someone’s going to ask a good question, or an idea will come up that we want to explore. I’ve also really prioritized getting to know everyone in the room very well. I love the math, of course, but knowing who the students are makes a big difference.


The past year has brought about difficult new realities. For those entering adulthood—dubbed Generation Z—a return to “normal” will involve fundamental change. In this issue, the Milton community looks toward the future and discusses how we will work, learn, laugh, cry, and live together in the decades ahead.