Conversations with the Head: Rebecca Jackman, Assistant Head of School

Jennifer Borman '81 and Rebecca Jackman don't do small talk. From the moment they sit across from each other, they instantaneously pick up threads of ongoing discussions. There are changes to the re-accreditation process to consider, faculty-staff meeting topics to review, upcoming events to coordinate—though one might assume, watching from a distance, that they were simply catching up rather than discussing the less scintillating aspects of running a school. "It's a great partnership," Jennifer says. "It is fun, it is generative, it is full of mutual respect and really good communication." Hired as a chemistry teacher in 2001, Rebecca became Assistant Head of School in 2017 to provide the kind of nuts-and-bolts oversight of Commonwealth's academic program that allows Jennifer, like Bill Wharton before her, to focus on the (vast) big-picture planning inherent to being Head of School. Together, Jennifer and Rebecca tackle the micro and macro of school operations, with an ear to the ground and an eye on the future.

What falls under the purview of the Assistant Head of School, exactly, and what is your working relationship like?

Rebecca Jackman: One of the themes over my time at Commonwealth is how we've grown and professionalized. We're still scrappy, but the Assistant Head of School role was established because it was becoming clear that the headmaster doing all of the administrative work was increasingly untenable, even in a small school like ours. My job focuses on the day-to-day of the student and faculty experience. I make sure classes are happening as planned and the arc of the academic program makes sense; that it's a challenging, engrossing educational experience; that students and teachers are supported and have what they need to thrive; and that parents know that they're sending their children to a place where they will get a wonderful education. Those are the domains that I'm always thinking about.

Jennifer Borman: You and I have had several wonderfully unresolved conversations about what's yours, what's mine, and what's ours. Budgets, fundraising, facilities, and trustees' work are mine. You have a meaningful role in the oversight of the quality of the academic program and student experience, which is what matters most in high school. Almost everything each of us does is connected; still, I think you have a huge portfolio of incredibly central work.

RJJ: Thank you! You do a better job of articulating the big picture—which is part of your role, not mine!

You both still find time to teach; how does stepping in front of the classroom feel at this point in your careers, and how does your teaching practice influence your work as school leaders?

RJJ: At five years old, I knew I wanted to be a teacher. Getting to go into the classroom every day and connect with my students and uncover the world of chemistry for them never gets old. When other aspects of my job are trying, being present with students for forty minutes in a classroom is really energizing and reminds me why it's all worth doing. We were just talking [in Chemistry 2] about kinetics and how to figure out the change in the concentration of reactants over time. Suddenly, the students had this moment of, "Oh, maybe we need some calculus for this," realizing there's a direct connection and application of something they're studying across disciplines—that's just fun to see! And the counsel Jennifer has given me about thinking of faculty meeting discussions much like a classroom discussion has been really helpful.

JB: For me, teaching is definitely fun, but I also find it just makes me a smarter leader in the sense that I have regular insight into our students—how sophisticated they are in their thinking as well as what their blind spots are, what their strengths are, what their habits of mind are. Any decision I might make is going to be much more informed given the fact that I'm not just having incidental contact with students. Teaching changes our relationship to our colleagues in a good way, too. The shared experience—the fact that we are all grading papers, taking attendance, having exhilarating and sometimes deflating days in the classroom—creates a different kind of faculty culture, I think.

RJJ: It helps foster mutual understanding and respect. And, for me, the student advising piece matters as much as the teaching. Through my advisees, I have a lens into what it feels like to be a tenth grader or an eleventh grader, as well as a window into the impressive work my colleagues do every day and how they create exciting classroom experiences for students.

How do you balance the day-to-day running of our academic program and long-term planning?

RJJ: I love the cyclical nature of schools. You get to go back into the classroom every day, and if you didn't do a great job the day before, you have the chance to do a great job today. You keep growing and learning, both on a small scale every week and on a larger scale every year. But it can also feel hard to find a moment in that cycle when it feels as if there's time to introduce a change. You can't just say, "We're going to pause the day-to-day operations of educating a child and focus on this long-term project we want to do." The key, I think, is identifying just one or two longer-term priorities to work on in a given school year—more than that and you don't make progress on any of them—and identifying a series of smaller steps that are manageable, while also running a school, but that will move you in the direction of change.

JB: One of the many things I like about working with Rebecca is that she's not complacent about anything. She loves Commonwealth and esteems the institution, but she's not just interested in maintaining the status quo. She's constantly asking: what could be even better? But there's no change by fiat here. We are deeply collaborative with faculty and staff, and we're thinking about both our priorities for making Commonwealth even stronger and our colleagues' priorities for improving their individual classrooms. How do we lead from the top down and the bottom up?

RJJ: The notion of shared stewardship very aptly describes the sort of investment that all of our colleagues feel in Commonwealth. There's a desire to make sure that everything we do improves the place—and an appreciation for how complex the system is and the breadth of potential consequences. If you change one thing over here, how will it shift things over there? If we're going to perturb the system, we're going to be deeply intentional about it.

How do you provide cohesive leadership for all academic disciplines, and what does the arc of working with faculty over the school year look like?

JB: Commonwealth has had a long and vibrant history of faculty autonomy, and that autonomy has bred creativity, passion, and these amazing courses that grow out of deep scholarly interest and expert teaching honed over the years. However, when there are shared agreements on things like DEI (diversity, equity, and inclusion) priorities, grading, and student attendance expectations, we make much more progress than we would having people do it their own way. Rebecca and I are in constant conversation about those shared agreements as well as how individuals and departments function here and the kind of support they need. You see many of the fruits of those discussions in our weekly faculty-staff meetings: every time we have a change in mind, whether fairly minor or somewhat less minor, we vet it with our colleagues, and we expect to hear a wide variety of opinions. Then we make use of those opinions and circle back and say, "Here's the next step."

RJJ: A good example of that process in action is our new ninth-grade seminar. We took a step back to think about what used to be three distinct ninth-grade classes as this holistic, yearlong course designed to introduce new students to all of the different aspects of the Commonwealth experience within the building, within the city of Boston, even within themselves. We started planning last year, we brainstormed with faculty and staff at our final meeting of the year, then we had really fruitful conversations over the summer involving a whole series of people from different departments, and we've been sharing progress with the whole faculty and staff as we go along.

You both have deep roots at Commonwealth—Jennifer as an alumna and Rebecca as a teacher for the past twenty-two years. What's changed since you first came here, and what are the throughlines?

RJJ: When I first started at Commonwealth, the focus really was on being this very intensely academic place. In our individual ways as advisors, we would work to help move students from fledgling young adolescents to fully fledged college students and adults in the world. We're still intensely academic, but attending to students' holistic needs has become more of a focus for us as the world has changed.

One thing that's remained constant is my incredible set of colleagues, even if many of the characters change over time. When I think about why I took the job at Commonwealth in the first place, I remember having my interview with (then-Headmaster) Bill Wharton and a group of faculty that felt just like grad school—except not everyone was a chemist! That was very exciting. They were all passionate about what they taught but united by their interest in being a part of this community and working with adolescents.

I think, fundamentally, the students have not changed either. They still arrive as fourteen-year-olds just taking the subway for the first time, and they mature into sophisticated young adults. How they develop over that time is pretty incredible to see, and the trust they have in the adults in the building, seeing us as partners in that process of becoming independent, is unchanged, too.

What has changed is me. When I started at Commonwealth, I had just finished my postdoc, and I was closer in age to the kids. Now I'm older than many of their parents, and I'm a parent myself. I have gone through so many different life stages that my relationship to the students and how they see me has shifted. That's just interesting to absorb.

JB: There is much that is recognizable and beautiful from when I was here as a student: the intellectual spark, the love of learning, the sense of community, the quality of the mentoring. Then there's lots that feels different, because I do think the school has changed in some of the ways you mentioned, Rebecca, and all to the good. I do spend time wondering about what parts of adolescence are relatively classic—the search for identity, for example—and what feels different about being a teenager in the twenty-first century. I feel like it is always worth revisiting how we're preparing our students for the here and now as well as life after graduation. How are we speaking to the needs of the future?

We've been reflecting on Eric Davis' legacy at Commonwealth and the impact of extraordinary teachers. How do you identify someone like that in the hiring process? Can you capture lightning in a bottle?

RJJ: I can think of so many people who have come to Commonwealth who were superb in their field and superb as teachers; some of them have stayed and continued to teach, and others have been pulled back to academia or elsewhere. You can't predict it, or at least, I can't predict it. I mean, when I arrived I thought I would stay for five years!

JB: I do think there really is an impressive amount of professional longevity here. I think the healthiest schools have a cohort of people with a long-term commitment—but some turnover is wonderful, too. You want to have teachers in their twenties and thirties and forties and so on, because it provides a much richer experience for our students. And you and I and our colleagues are prioritizing a very intentional effort to recruit for diversity in many dimensions. Diversity of age, level of experience, disciplinary background, and also identity has been a real focus of our work.

Related: Remembering Eric Davis

How do you think about the impact of the pandemic on today's students?

JB: I feel like we are collectively—not just in this building, but all over the world—trying to take stock. I don't think any of us knows the full impact, but, at least at Commonwealth, the observing, listening, assessing, and comparing feels very active and fruitful here.

RJJ: We're especially attuned to our students who spent their middle-school years in the height of COVID. A particular kind of loss happened there. So much of that time is spent making social connections and learning general executive function skills—how to manage your time, how to keep track of assignments, how to study. Part of our rationale for reenvisioning our ninth-grade seminar was to help meet those students where they are.

JB: The interruptions and discontinuities of students' pandemic education are showing up in the classroom now. There are real struggles—and real grief—to attend to from the pandemic. Let's figure out how to serve those needs, and then let's think about what we might harvest from the experience. I never want to think about the pandemic as only losses or only deficits; it may breed long-term resilience or adaptability or appreciation and gratitude or an additional dose of Carpe Diem that may serve students in helpful ways. I feel like we just don't know yet.

RJJ: One of the things I've really valued about you as a leader, Jennifer, is your deep respect for the institution but also your willingness to ask us to think about why we do something the way we do it. Maybe there are really good reasons; maybe we should consider doing things another way. But that thoughtful questioning is what allows us to grow.

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