Skipper Returns to Boston Schools

Mary Skipper, Ed.M’06, knew by the third grade that she wanted to be a teacher. She loved learning, and her mom, a single mother working three jobs who almost dropped out of high school, made it clear from an early age that learning would be different for her daughter. 

“She did not want me to struggle as she had to in life,” Skipper says of her mother, “so she reinforced from my earliest memories how important it would be for me to work hard in school and get the best education possible.”

Skipper listened to her mom, but, she says, she wasn’t the easiest student on her teachers.

“I was impatient, asked many questions, and could get distracted,” she says. Luckily those teachers stepped up for her, acting almost as surrogate parents. “I had so many excellent teachers who met me where I was, engaged me, invested in me, and shaped who I was and what I could do. Honestly, by third grade, I just knew I wanted to be a teacher so that I could try to be that difference-maker for other students.”

This week, Skipper became that difference-maker as she stepped into her new job: superintendent of Boston Public Schools (BPS), the sixth person to hold the position during the past decade. She took over from another Ed School alum, Drew Echelson, Ed.D.’13, who has been Boston’s interim superintendent since June. Before that, Skipper served as superintendent of Somerville Public Schools, where dropout rates fell, and graduation rates rose during her seven-year tenure. She started her career following her third-grade dream: teaching Latin and Greek at a private Boston high school before cofounding TechBoston Academy (TBA), a pilot school for grades 6–12 in Boston that today scores in the top percentile on state testing and has a 94% college placement rate.  

This fall, Skipper spoke to Ed. about her move back to Boston schools; the importance of why, what, and how; and having the Ed School in her village. 

When the superintendent announcement was made, you were with Boston Mayor Michelle Wu at TechBoston Academy, where you were the headmaster for a decade. At the press conference, you said there wasn’t a day driving to that school where you didn't get excited. “That’s what we need for BPS,” you said. How will you bring this energy back to the district, especially for teachers who are tired after several years of COVID upheaval?
My experience is that people feel motivated and confident when they understand the why, what, and how of their work. When people have the resources and decision-making power to carry out their responsibilities successfully and see significant accomplishments, they gain more confidence and feel fulfilled in the work. As a school leader at TechBoston, my “why,” “what,” and “how” were always clear, and if I ever lost my way, I had my colleagues and students to help remind me. I was blessed to have so much support to do the work that was important to us as a community. So, every day I went into TBA, I was excited about the possibilities for our students, even on days when the work was difficult or frustrating. I always told myself that when I stopped being excited, that was the time for me to step aside and let someone else have that opportunity. I want to work hard so everyone in our BPS community can feel that same fulfillment and purpose. 

COVID made that harder.
The last two years have been extremely difficult for educators, especially teachers. Almost overnight, they had to transform their teaching from in-person, where daily they could see the “why” in the faces of their students and know they were accomplishing their goals as a teacher, to a year of remote learning filled with empty screens and expressions. And this past year, everyone had to learn how to do the basics all over again, as students and teachers had to relearn their “why” and “what” of learning and teaching, all while struggling individually and as a community with the trauma of illness, loss, and separation. 

How will you support them?
From a support standpoint, we have to meet our educators and students where they are and help them find their joy again. We must be ready to provide lots of support as we, as a community, redefine teaching and learning and how we can be effective in our roles. I believe this coming year will be less about reaction and more about reconnection for educators and students. 

Looking back, what brought you to the Ed School and what impact did that time have on your career?
When I attended HGSE, I was the school leader at TechBoston. I wanted TBA to be successful and sustainable, and I knew to be a good leader, I had to immerse myself in learning how to do that. I wanted to be in an environment where everyone I came in contact with could teach me something from their experience, knowledge bank, and thought process. I also wanted the opportunity to learn not just from reading an expert’s book but from having an authentic engagement with that expert. I had read so much of Howard Gardner’s and Ted Sizer’s work as we wrote the concept paper for TechBoston. Growing those ideas by taking their classes and many other outstanding professors at HGSE felt like a dream. To this day, I feel so blessed that I had that opportunity to attend HGSE and learn from my fellow students and professors. I have many lasting friendships and mentors from my time there that continue to help develop me personally and professionally.

Do you see those connections continuing now that you’re in Boston?
Absolutely. HGSE and its students are such a fantastic resource for our community. When I was in Boston as a school leader and district leader, I always had deep partnerships with students and professors at HGSE that added so much value. As we undertake the work in BPS, I am hoping to continue to build on the strong partnership that is in place with HGSE. We have a great deal of work to ensure we meet our students’ academic, social, emotional, and physical needs. We need a village to do this work, and HGSE will be one of our key partners. 

What’s the thing that’s most exciting you about this new opportunity in Boston?
So many things excite me about returning home to BPS: the chance to work with and build a team responsible for serving the students and families of Boston, where I live and have raised my family. Serving as the superintendent of Boston Public Schools is the chance of a lifetime. Engaging with our nonprofits, post-secondary partners, the business community, and foundations — building up that village in a city where the mayor, city council, and school committee all want what is best for our students — is a superintendent’s dream. And all of this exists here in Boston. There will be many challenges along the way, but I believe every challenge is also an opportunity. And right now, I am thankful for this opportunity.