She was on a whirlwind tour of an elementary school, running late on a day crammed with appointments, but Mary Skipper couldn’t resist.
Spying a fourth-grader puzzling over a math book that December morning, the Boston Public Schools superintendent stopped and peered over the boy’s shoulder. She took his pencil and sketched little cars.
“If you picture the cars — eight, and eight, and eight…” she said. “Draw it out.”
Four solid minutes later, she turned back to her entourage. “Sorry, guys,” she said with a grin. “I used to teach math.”
It was classic Skipper, who despite holding one of the most high-profile executive jobs in Boston, loves diving into the individual struggles of children, teachers, and principals, and talking them through with granular specificity and a scrappy familiarity. She’s a hugger. A sympathetic nodder. And she has a penchant for breaking down seemingly impenetrable problems into smaller chunks, and relentlessly chipping away at them.
Now, after leaving the helm of Somerville’s schools last fall to lead BPS, Skipper, 55, is confronting the challenge of her career: turning around a school system that fails thousands of children every year.
Can she succeed where so many before her have faltered?
Boston’s schools are operating under threat of a takeover by the state, which in a report last spring described the district’s “entrenched dysfunction” and “systemic disarray” in withering detail. Less than one-third of elementary and middle school students are proficient in reading and math. Enrollment has been hemorrhaging in recent years, as parents with means decamp to the suburbs, charters, or private schools.
Skipper is Boston’s sixth superintendent in a decade. Her predecessor, Brenda Cassellius, vowed she’d hand incoming kindergartners their high school diplomas one day; she left as they finished second grade.
Four months into Skipper’s tenure, it’s early to draw conclusions. But there is real optimism out there — a sense among many principals, teachers, school officials, and outside observers that Skipper is starting to drive the change the school system desperately needs.
“She knows the real truth of what is, and what isn’t, happening in Boston,” said Jeri Robinson, chair of the Boston School Committee. “There’s a collective, deep sigh of relief — even though we’ve got many more mountains to climb.”
Skipper would blend in at any teachers lounge in the city. She doesn’t wear fancy clothes, isn’t given to making grand speeches. She has a disarming ability to connect with people, asking question after question, her bright blue eyes searching deep into theirs. A longtime Dorchester resident, Skipper speaks with a witty confidence, parrying questions in a slight Boston accent, with the informality of a chatty grocery store clerk, a part-time job she held from age 14 to 29.
She isn’t shy about much, including discussing her deep Christian faith, which was nurtured by her Irish-Catholic family, but deepened in her 30s as she fought breast cancer. In her office, a small cross — unusual in a public school setting — hangs on the wall beside pictures of her husband, Peter, a retired Boston College High School religion teacher; her adult children, Kassie, Lihlani, and Peter; and her dog, Otis. A large Pride flag also hangs nearby, along with an array of the kind of inspirational quotes teachers like to post on the classroom wall: “What would you attempt if you knew you could not fail?”; “Life isn’t about waiting for the storm to pass. It’s about learning to dance in the rain.” And — in a nod to her stature — that line from “A Midsummer Night’s Dream”: “Though she be but little, she is fierce.”
What most distinguishes her from her immediate predecessors, many of them out-of-state imports to Boston, is her intimate knowledge of the district. She worked in BPS for nearly 20 years as a high school Latin teacher, founding principal of TechBoston Academy, and assistant superintendent for high schools, before going to Somerville in 2015. Her daughters went to the Roger Clap Elementary School in Dorchester, and all three of her children attended Boston Latin School.
Her years running TechBoston, an innovative school in Dorchester that espouses project-based learning, may have been most formative; as principal, she learned the importance of delving into the details. Skipper came to know all of the school’s 1,100 students and their families, colleagues said, and established regular meetings where educators tailored each student’s schedule and teacher assignments to fit their individual needs. President Barack Obama visited the school in 2011 to hail it as a national model, praising “Skip” for the school’s high math and science scores, college enrollment, and graduation rates that outperformed the rest of the district by almost 20 points.
“You need to be in the weeds of your school to know how things work,” she said in a recent interview. “At a district level, the same holds true.”
As superintendent, her first order of business isn’t the weeds so much as the full-grown trees standing between her and the system she wants to lead. It falls to her to carry out the agreement Mayor Michelle Wu reached with the state education department last summer, when the new mayor, who has promised a massive school rebuilding project and “academic excellence across all our schools,” averted a state takeover. The 11th-hour deal came with a long to-do list, and a series of rigid deadlines.
The sheer breadth of that list is dizzying. In three years’ time, BPS has to complete a major overhaul of school safety, transportation, special education, English language instruction, data collection, facilities planning, and low-performing schools.
“When people see me now, they’re like, ‘Are you OK?’” Skipper quips. She says she loves the job. But she is matter-of-fact about the enormity of the task ahead.
“Any one of them would be an undertaking. All of them combined together is a massive undertaking,” she said. “In this first year, we have to lay a strategic foundation, so that we can then be able to work on all of them at the same time.”
The pressure is on. Education Commissioner Jeff Riley, a BPS parent himself, is already sounding impatient; in a recent state board meeting, he scolded the city for its failure to get buses running on time and repair school bathrooms. He also had warm words of welcome for Skipper, an old colleague from his days at BPS, who couldn’t be faulted for problems she inherited — yet.
To empower her deputies to speed projects along, Skipper has restructured the Central Office, reducing the number of direct reports she has from 15 to three, who oversee academics, operations, and family and community advancement. She’s assigned additional staff to each of the district’s nine “regions” — mini-districts of about a dozen schools each — to help schools with issues around hiring, facilities, and buses, as well as literacy and academic instruction.
That seemingly modest adjustment has had considerable effect, allowing principals to delegate a raft of time-sucking responsibilities, like dealing with late buses and scheduling teacher trainings, freeing them up to focus on students and teachers, said Gene Roundtree, the superintendent for Region 8, which includes high schools in Dorchester, South Boston, and Jamaica Plain.
“She has configured the district to have a more responsive culture,” he said.
Simple-sounding but consequential changes like that are Skipper’s signature, colleagues said, the hidden hand of a bureaucratic surgeon. In Somerville, she directed staff to hold weekly meetings on every single student who was failing or chronically absent to make sure each got precisely the help they needed, said Andre Green, a Somerville School Committee member. The dropout rate plummeted.
“The things Mary will do to stabilize BPS, and make it more student-centric, the public may never actually see,” Green said. “But it will slowly, surely, and steadily improve student outcomes.”
Skipper has tried to cultivate trust with the Boston Teachers Union, which has the proven power to make a superintendent’s priorities achievable or to make a superintendent miserable. Here too, the agenda starts with the basics. When the district failed to deliver some 9,000 educators the raises they were owed, Skipper promptly acknowledged this was unacceptable, and promised she would fix the problem.
“She’s very no-nonsense,” said Jessica Tang, the union’s president. “She is thoughtful. She listens.”
Skipper is also paying close attention to principals. This is savvy politics; a group of high school principals all but did in Cassellius barely a year after she started by declaring, in a scathing letter, that they’d lost confidence in her leadership.
But it is much more than that. As she learned in her own time as a principal, school leaders are key to solving the school improvement puzzle, since they are hinge points between the administration and what’s happening on the ground. They represent whole communities of parents and kids, and tend to understand their needs well.
Everywhere she goes, as she visits schools and talks with principals around the city, Skipper says she is looking to see “where the foundation is soft … and what needs to be rebuilt.”
As dawn broke one frigid December morning, Skipper visited English High School for a celebration of its academic progress; after 12 years, it was exiting “transformation” status, the state’s label for underperforming schools. Christmas music drifted through the hallways. Teachers wore Santa hats.
But soon, Skipper was holed up in the library with the principal, who described a problem threatening to undermine those gains. The district had unexpectedly assigned to English High dozens of new students whose severe mental health issues were classified as disabilities, and the school was struggling to handle them all.
“It’s just too many kids with concentrated need in one place.” Skipper nodded. She asked about the numbers, the classrooms, the staff, their qualifications, even the furniture (were there any bean bag chairs?, Skipper wanted to know).
“This is something we have to drill down on,” she said, at last, to her top academic deputy, Linda Chen; later that day, she would talk with the district’s chief financial officer about capping the number of certain special-education students assigned to each school, and sending a team to English to learn more.
The principal, Caitlin Murphy, seemed grateful. She wanted to help as many students as possible, but without the proper staff and classrooms, she said, “We can’t do all the things.”
The state improvement plan has a heavy focus on operations, though, and some worry that’s a distraction from Boston’s central problem of weak academics, which must be addressed with force and ingenuity to stop frustrated families from fleeing BPS. As the state has noted, some 14,000 Boston students — nearly one-third of the district — attend schools ranked in the state’s bottom 10 percent.
The pandemic only made things worse by widening achievement gaps among students of different backgrounds, leaving students from low-income families, Black and Latino students, students with disabilities, and English-language learners trailing their peers.
Many parents are at their wits’ end and sick of being told hope is just around the corner. Tanya Nixon-Silberg, who lives in Jamaica Plain, said the Mendell Elementary School pulls her fourth-grader out of math lessons to receive reading help, sacrificing one core academic subject for another.
“This is not an experiment,” Nixon-Silberg said. “This is my child’s schooling, right now, in real time.”
Skipper says she feels the urgency. She experienced the transformative power of a good education in her own life; she grew up poor in a tiny two-bedroom duplex in Arlington shared with her single mother, aunt, uncle, and two cousins. Skipper’s mother, who worked in her school cafeteria, desperately wanted her daughter to go to college. And young Mary made good on that dream, becoming valedictorian at Arlington Catholic High School, and winning a full ride to Tufts, where she graduated with a bachelor’s degree in English and Latin, before going on to earn three master’s degrees, one each from Tufts, Harvard, and Columbia. She knew early on she wanted to become an educator, inspired by her fifth-grade teacher, Mrs. Siegel, whose fun, free-spirited lessons sometimes featured the music of Cat Stevens and sparked in her a love of reading.
Skipper also knows what it’s like to miss lots of school and fall behind — and that, with the right instruction, it’s possible to catch up. When she was a girl, a life-threatening allergic reaction to penicillin kept her out of class for six weeks of second grade. She missed phonics lessons, affecting her ability to spell for years. She’s felt the sting of the pandemic, too; she was hospitalized with COVID on Somerville’s first day of school this academic year and remained in quarantine during Boston’s.
“First time ever in 33 years that I missed an opening,” Skipper said. “I was like, ‘You’ve got to be kidding me!’”
As students recover from the pandemic’s missed lessons, Skipper is looking to strengthen the core of BPS academics. Cassellius instituted a new literacy teaching framework that includes a greater focus on grade-level content that’s relevant to students’ lives, as well as phonics and word-decoding, because research has shown these to be the most effective methods of reading instruction. In her first months on the job, Skipper has channeled much of her time and energy to ensuring the new approach is understood and implemented by principals, and reinforced by literacy coaches assigned to each region.
Skipper is also thinking more holistically. Kids who have healthy, creative lives outside of school tend to be the ones who thrive in school. Skipper dreams of a system that offers help with essentials, such as food and housing, to every family who needs it, as well as the extras that encourage children to love learning and feel they’re citizens of the world — overnight summer camp, travel, violin lessons.
BPS spends more per student than affluent districts like Lexington, Needham, and Newton, but its students have much higher levels of need; two-thirds are poor, one-third are learning the English language, and one-fifth have disabilities. Even the district’s staggering $1.3 billion budget can’t overcome all the inequities that Boston students face. Still, Skipper sees herself as a resource broker for her students, reaching out to businesses and nonprofits eager to help, an assembly she calls “the village.”
This is another area where Skipper’s local experience helps. She knows the nonprofit players in town, so she can move ahead quickly and confidently with those she feels she can count on.
For EdVestors, a philanthropy that started funding private music lessons for about 200 BPS students this year, “it looks like starting a conversation with, ‘What can we do next?’ rather than explaining what we do,” said chief executive Marinell Rousmaniere.
Skipper is also searching for ways she can help kids who are on not on anyone’s radar — the hundreds of teenagers who drifted away from school during the pandemic. The plight of these young adults, some now in their early 20s, haunts her.
She’s asked the YMCA to offer them space for classwork in its buildings. They are “neutral zones,” she told the nonprofit’s executives in a recent meeting at the district’s headquarters, that don’t carry the negative associations many dropouts have with schools. Perhaps, she suggested, a phone app could be developed to help these young people access an array of services at once — food assistance and mental health services, YMCA gym memberships, museum and T passes.
“It all speaks to me as her seeing kids as full humans, which you would hope for, but when you’re being held accountable for things like scores and rates, it can be harder,” said David Shapiro, the chief executive of the YMCA of Greater Boston. “There’s just a certain realism, and a certain student-centeredness.”
Whether Skipper can withstand the bone-crunching pressure of Boston school politics remains to be seen. Just two superintendents in the last half-century — Thomas W. Payzant, who served from 1995 to 2006, and Carol Johnson, who led from 2007 to 2013 — survived to reach the six-to-10-year threshold Skipper says it will take to truly turn BPS around.
Already there are rumblings of discontent here and there. Some parents and advocates have voiced concern that Skipper isn’t sufficiently focused on anti-racism work. They say district staff and schools aren’t being pushed to make racial justice a priority in all decisions. And that under Skipper’s streamlined office structure, the lead administrator for reducing achievement gaps now no longer reports directly to the superintendent, which civil rights advocates had fought for for years. Skipper said she has heard the concerns about the reporting structure and would soon address them in her new organizational chart.
Such complaints might seem like overreaching, or at least premature, given how brief her tenure has been. But critics say if the superintendent doesn’t clearly designate racial equity as an overarching priority, she is endorsing the status quo, which has long failed students of color.
“I worry that we’re going in the wrong direction,” Kimberley Williams, BPS’ director of social emotional learning and instruction, said during a December meeting at which she and other Black educators decried equity chief Charles Grandson’s loss of rank in the superintendent’s inner circle.
Taking the argument directly to the classrooms, Edith Bazile, a former BPS special education administrator, said the fact that 80 percent of Black and Latino third-graders aren’t reading on grade level is an emergency that demands more drastic action — such as tossing the district’s early learning curriculum entirely and starting afresh. Skipper, she said, isn’t going far enough, or moving fast enough.
“We’re talking about a wide-range failure to learn to read,” Bazile said.
Skipper said she’s building a strong foundation of reading instruction and it will take time before teachers in all 119 schools are trained and on board. But she’s confident in her approach, which prioritizes district staff visiting classrooms to ensure they’re using high-quality instructional materials. And Skipper says she is entirely committed to racial equity, and that she will win over her skeptics.
“If a year from now, people continue to feel that way, or even by the end of this year, then it’s something I would have to look at more deeply,” Skipper said. “Equity is foremost for me in the work that we do.”
The months to come will undoubtedly test Skipper’s ability to nimbly navigate these kinds of complaints, as well as to address growing concern about school violence, not to mention the random crises — such as the teachers’ payroll mess — that seem to rise up constantly in BPS.
In the longer term, she will have to make tough, consequential decisions, such as changing bell schedules to get buses running on time, and closing schools — the system has far too many, given the steep declines in enrollment. These decisions are likely to cause political uproar, but they must be reckoned with if the system is to improve.
To survive and thrive in the job, she will need Wu’s support. Though the mayor and Skipper seem tightly aligned so far — Wu said they text, call, and meet often, but she trusts Skipper to run the day-to-day without intervention — some parents worry that Wu, herself a BPS parent, isn’t saying enough about education. In her State of the City address, Wu spent only a few minutes of her half-hourlong speech on schools, deferring a deeper dive: “Thatʼs for next yearʼs State of the City.” A mayoral spokesman said Wu considers schools a top priority and has made significant early investments in reforms; last year was spent building the education team and making plans, he said, but next year will see more action.
Skipper says she feels good about her partnership with the mayor. She says she knows she will face opposition on the road to progress, and she’s ready. She has, she says, a strong “inner compass.” Though she be but little, she is fierce.
“You have to make decisions, and very seldom are they 100 percent popular,” Skipper said recently, sitting in an airy conference room adjoining her office. Outside, amid the bleak midwinter cityscape, the purple and orange hues of the mural “Reflection Eternal” glowed over Nubian Square.
She smiled. “I learned a long time ago that really who I do this work for are the students.”
In the midst of the BPS superintendent search last spring, as she reckoned with her husband’s recent heart attack and weighed whether to have her name publicly announced as a finalist, she prayed before bed one night, asking God for a sign. She woke at 3 a.m. to find that, a couple of hours earlier, an e-mail had landed in her inbox.
It was from a student she’d taught 33 years earlier at Boston Latin Academy. He was constantly restless in class, she recalled, but she saw his brilliance, and gave him a mythology book to read. It fascinated him; he became a leader on the school’s Latin trivia team.
All these years later, the man — now a scientist — was writing to thank her. His daughter was now a teacher in Boston. The care and attention Skipper gave him, he wrote, was a high point of his BPS experience and “one of the reasons that I suggested to my daughter to consider teaching as a career.”
It was a reminder, Skipper said, of the power schools have to change children’s trajectories, like her own. It is a precious thing, that power, and the schoolchildren of Boston have to hope that the pursuit of it will drive her every day.
Naomi Martin can be reached at firstname.lastname@example.org.