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Possibility meets pragmatism as new Boston superintendent gears up for race to meet state deadlines

New Boston Superintendent Mary Skipper.David L. Ryan/Globe Staff

It is an assignment tougher than any Mary Skipper has faced in her career: turning around a 49,000-student school district under fire from state regulators, in the face of entrenched dysfunction, distrust from families, and persistent failure to reach its most vulnerable learners.

As the new superintendent of Boston Public Schools, Skipper has just six weeks to meet the state’s first deadlines for improvement — even though she won’t be in the job full time until the fall because she is winding down her tenure running the Somerville schools. She has joked about working 18-hour days this summer, splitting her time between the two cities.


For this driven leader, who projects a calm and steady confidence as she moves briskly through her days — pausing often to listen intently — that projection may not be far from the truth.

“We have a ton of work to do for students and families, and the agreement with the state offers a clear scope and concrete, specific steps,” she said in an interview Saturday. “This is an opportunity to start doing things differently [in BPS], with the goal of more nimbly responding to the needs of our kids.”

Her can-do attitude notwithstanding, the task before Skipper has been widely described as impossible and unrealistic. The state-mandated plan for improving BPS was finalized by Mayor Michelle Wu, state education Commissioner Jeffrey Riley, and top BPS leaders two days before Skipper was selected. Though deadlines in an earlier draft were even more aggressive, with some tasks slated for completion in July, the ultimate agreement gives the district little time to address problems that have persisted for years, and in some cases, decades.

Of the 24 mandates agreed on by the state and city, 10 must be completed by Aug. 15. None will be easy to achieve. By that looming deadline, BPS must develop a plan, policy, and procedure manual to improve special education, and hire a team to make the changes; create a plan and a system to ensure all English learners get needed services; commission a safety audit and improve its system for responding to family complaints; review the status of bathrooms at all schools and plan improvements; and launch an evaluation of its transportation system.


Experts say Skipper, 55, will need to tread carefully in her early days, striking a balance between ambition and pragmatism as she charges ahead.

“It’s unreasonable to expect an institution to transform itself that quickly,” said Ebony Bridwell-Mitchell, an expert on education leadership and reform at Harvard Graduate School of Education. “But you can focus on what is possible by Aug.15, you can be specific about what can be accomplished, and you can talk about your vision for future transformation.”

Mayor Michelle Wu held a press conference outside TechBoston Academy in Dorchester with incoming BPS Superintendent Mary Skipper. Skipper was once principal of the school. David L. Ryan/Globe Staff

Also critical, Bridwell-Mitchell and other experts said, is for Skipper to be clear and specific about what the state can do to help her be successful.

Known as a direct and detail-oriented leader with a track record of building teams and inspiring teamwork, Skipper brings long familiarity with Boston to the high-stakes sprint before her. A longtime Dorchester resident whose three adult children attended Boston schools, she worked in BPS for nearly 20 years before becoming superintendent in Somerville, and knows the system well.

She also knows Drew Echelson, the acting superintendent who will be filling in for her this summer, and predicts the pair will work hand in glove to meet the deadlines. In an interview Friday, Echelson said that much of the work on the first improvement goals was under way before the plan was finalized last week. He said he has spoken to Skipper about 20 times since the School Committee approved her appointment, and the two planned more conversations this weekend.


“Listen, do I think we’re going to hit every single thing and every single benchmark on there? Probably not. As an organization, I can commit to you that we’re going to go down trying,” he said. “And I think we’re really well positioned to do quite well. ... We cannot be in a position where we are not making progress for our students or families.”

A new, senior level manager will coordinate work on the state plan, along with several other staff, he said, to “ensure that we are making progress ... and help us get unstuck in areas where we see barriers.” The goal is to succeed at the step where previous overhauls have failed: the leap from planning to implementation.

In the Saturday interview, Skipper said she is delving deep into data and audit reports this weekend, and plans to meet soon with school and union leaders, among others, to ask about their experience and priorities. She said she feels hopeful and excited, and buoyed by the hundreds of supportive texts and e-mails she’s received from nonprofits, businesses, and others saying “’We’re ready, and we want to help.’”


“That’s powerful,” said Skipper. “They want to be part of the solution, and this is the time, when we all can come together.”

Skipper likely won’t have as much time for community outreach as her predecessor, Brenda Cassellius, who visited all 125 schools during her first 100 days on the job in 2019. But conversations with school leaders and community partners is still a wise priority, said Mary Walsh, Kearns Professor of Urban Education and Innovative Leadership at the Lynch School of Education at Boston College.

“What she’s confronted with is building a village on a very big scale,” Walsh said. “She’s trying to establish consensus around a positive vision, with everyone at the table, of what education every child deserves.”

Somerville School Committee Chairman Andre Green said Skipper will be helped by her ability to break enormous undertakings down into a series of smaller, less overwhelming tasks. “She knows it’s all the little things that move the ball forward,” he said.

When Skipper set out to improve graduation rates in Somerville, her approach was surprisingly granular, said Green, as she engaged principals in examining the records of individual at-risk students to see how risk could be reduced.

“It wasn’t flashy work,” said Green. “It was 1,000 small things. … In Boston, she’s not going to know every student. But she can expect that kind of thinking from her principals, and make that their mission, to serve individuals.”


Somerville Superintendent of Schools Mary Skipper spoke with students participating in The Calculus Project at East Somerville Community School in 2019.Aram Boghosian for The Boston Gl

Experts said Skipper can draw on her past work with state education officials — and her well-honed negotiating skills — to inject realism into the state plan. “You’re not going to fix everything overnight,” Walsh said. “But you can say, ‘Here’s what’s reasonable, here’s what we can do, here’s the big vision.’”

Marinell Rousmaniere, chief executive of EdVestors, a Boston education nonprofit that works with BPS, questioned whether the August deadlines can be met, given the demands of leadership transition, and the challenge of staffing shortages. Still, she sees the new improvement plan as “the best prospect for progress in quite some time,” as long as people remember it doesn’t encompass all the issues.

“The agreement alone won’t solve everything, but it is a blueprint for what is critical,” she said.

Margaret McKenna, former president of Suffolk and Lesley universities, questioned whether meeting every requirement of the agreement is doable, though she considers Skipper an exceptionally seasoned administrator.

“If anyone can do it, Mary can do it, but ... some of these things you can’t do because the personnel aren’t there to do it,” said McKenna, a former state education board chair and former Boston School Committee member. For instance, she said, the agreement requires school buses to arrive punctually 95 percent of the time, but a national shortage of drivers will inevitably leave the district scrambling for personnel to meet that target.

Francis Pina, a Charlestown High School teacher and policy fellow at Teach Plus, a nonprofit that works with teachers, said Skipper will also be challenged by her need to reacquaint herself with BPS.

“She’s going to need to learn what the challenges are around BPS for current families, and rebuild trust. BPS is different than the last time she was here, especially with the effects of COVID,” said Pina, who was among the panelists who questioned the two finalists for their public interviews.

Building trust is just one of the time-consuming items on Skipper’s to-do list, said Jeffrey Young, a former superintendent in Cambridge and Newton who now directs the education leadership program at Columbia University Teachers College. Another is creating a culture where people aren’t afraid to innovate, and establishing new protocols for problems ranging from late buses to school safety, so everyone knows what to do in a wide range of situations.

“If it took time for a problem to evolve, it takes time to solve it,” said Young. “She’s a human being, not a savior, and there is no magic wand.”

While problems abound, the district’s new leader cannot focus solely on deficiencies if she is to bring the city together, said Walsh, of Boston College. “These kids bring so much strength and resiliency,” she said. “It’s essential to acknowledge that, as we also address the needs.”

Skipper said she will strive to keep the city’s children front and center.

“The goal is to have students running into school because they’re hopeful and excited, and they know they’re going to learn,” she said. “There will be a lot of adult stuff in between, but it should be grounded in what we do for students.”

The Great Divide is an investigative team that explores educational inequality in Boston and statewide. Sign up to receive our newsletter, and send ideas and tips to

Jenna Russell can be reached at Follow her on Twitter @jrussglobe. James Vaznis can be reached at Follow him @globevaznis.