Heather Sugrue, who this summer became the new Upper School academic dean, has witnessed two decades of Milton Academy as a math teacher, house head, and most recently, 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 for 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, it was rewarding to use my math knowledge to collaborate with the adult community here. I found I really enjoyed that. I also felt that I was creating some 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 dorm and in my classes, but this new position gives me the opportunity to get to know more students while we’re supporting them and 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 supporting new faculty. 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—we try to be as supportive as possible.
I work closely with Kate Collins, 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?
There were a number of teachers who were hired while I was chair, and that’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 of 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 math, either explicitly or implicitly, for a long time. It begins in elementary school, where a lot of math skill 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 math 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 six or seven years ago. The thing that makes teaching challenging is also what makes it so 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, too, but knowing who people are makes a big difference.
What do you do outside of work?
I’m a big sports fan. I love the Patriots, I love the whole day of football, the tailgating, the grilling, all of it. I have a very short list of friends—luckily my husband is on that list—who want to go to the games when the weather gets a little colder. It’s so fun. We go to the Red Sox games a lot, but not so much the Bruins, because those tickets are so expensive.
My other primary role is being a mom, so I spend a lot of time at my sons’ hockey and baseball games. This season, I’m coaching the boy’s third- and fourth-grade basketball team for the fall session of the town of Milton’s outdoor basketball program. We love being in this town. I love country music, so I see a lot of concerts. Friday nights with my kids, we’re usually rewatching the Marvel movies in order. And we love to spend time on Cape Cod in the summer.
We live on campus, and my older son just started Grade 6 here, which is a lot of fun. I get to live Milton through the lens of a parent now.
