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In new podcast series, former and current Boston school superintendents reflect on the role — and what the district needs in its next leader

Outgoing BPS Superintendent Brenda Cassellius chatting with students in a first-grade class in 2019 at Winship Elementary School. Cassellius announced in February she will step down in June.Jessica Rinaldi/Globe Staff

Six former and current Boston Public Schools superintendents have all grappled with similar issues: longstanding structural problems in BPS, needing a reliable transportation system, and communication around hard decisions being made in the district.

Those are a few of the themes that emerged during interviews with the education leaders in a new limited podcast series that follows BPS’s search for a new superintendent.

The series, “Last Night at School Committee: The Search for A New Boston Superintendent,” was launched this month by the Shah Family Foundation and consists of in-depth conversations with community members, as well as former superintendents Michael Contompasis, Carol Johnson, John McDonough, Tommy Chang, Laura Perille, and outgoing Superintendent Brenda Cassellius.


Jill Shah, the Shah Family Foundation president, and Ross Wilson, the foundation’s executive director, have been following the city’s School Committee meetings for the last two years in their podcast as a way to inform and help summarize committee happenings for those unable to attend.

When Cassellius announced in February she will step down in June, the pair turned their efforts to the search and priorities for the superintendent.

They tapped the five former superintendents and Cassellius to weigh in on the significance of the role since “we often don’t talk to former superintendents once they leave the district, we don’t hear from them, they don’t have a chance to chime in,” Wilson said.

Shah said one of the things she and Wilson took from their conversations with the former district leaders is creating lasting change in the district takes time.

“It may be a problem that we’ve gone through six superintendents in 16 years; it doesn’t give anyone really much time to get anything done,” Shah said, adding there are things put in place that have been successful in bettering things in Boston schools, but there is also a lot that has yet to be done that former superintendents weren’t able to get to.


Each superintendent highlighted some achievements, while also discussing what they wish they had done differently. But each also raised concerns in the areas of inequities in school facilities, transportation problems, and communication.

“So therein lies the work for the next superintendent,” Shah said, “As well as it begs some questions about what the skill set is. What is really going to be most successful here in Boston?”

Wilson praised Johnson, superintendent from 2007-2013, in her episode for lowering the dropout out rates by about 40 percent, setting achievement standards by grade levels, and bringing in the Boston Debate League during her tenure.

But one area Johnson identified she failed in, that she hopes the next superintendent focuses on, is giving more attention to Madison Park Technical Vocational High School.

“I’m not sure where it is now because I certainly haven’t kept pace, but the economy, the jobs of the future, the current COVID realities, mean that our students are going to have to have different sets of both engineering and career and technical skills that Madison Park certainly could deliver,” Johnson said.

Cassellius, whose episode aired last Monday, said the next superintendent should prioritize funding capital projects, moving forward with a more regional approach for the district, and addressing declining enrollment.

She also said she’s concerned about Boston schools not having enough teachers, school leaders, central office team members, and food nutrition workers, and thinks the new district leader will need to hit the ground running on hiring.


When asked in the episode how the state’s review to take over BPS could impact the superintendent search and if it would’ve had an impact on her thinking about applying for the job, Cassellius said, “of course it does.”

During her episode, Cassellius also shared that the superintendent must have have a good relationship with the mayor, who often influences the district’s policies.

While her experience as the former Minnesota commissioner of education helped her manage political challenges, it can be difficult for a superintendent to navigate through “all the different voices” and come to an agreement to close gaps for Black and Latino children when it comes to systemic issues within the district.

“If you are able to bring around a common consensus, I do think that you can have change really quickly,” Cassellius said. “Unfortunately, we had the pandemic that was interfering with so much of what we were trying to do. But I think we were really going toward a common consensus on some of the deeper systemic issues within the district around equity.”

She said she hopes the next person to take the job stays as long as they can, but that people will judge her legacy based on changes she made in the district rather than how long she was superintendent. The next superintendent, she said, is going to have to take on tough issues. “They’re going to need the cover from their mayor and their School Committee.”


She added she’s grateful to have a School Committee and two mayors who supported her through the pandemic, and that the next person should continue to work with Mayor Michelle Wu to move the district forward.

“I think that the next superintendent is just going to have to really be ready for the different political winds that might come in the mayor’s office, as elections shift and change, as school committees shift and change,” Cassellius said. “You just have to be nimble enough to be able to withstand that if you possibly can, and do the best work that you can possibly do for the children and just stay centered on what is best for children and continue to speak your truth about what has to be done within the district.”

Adria Watson can be reached at adria.watson@globe.com. Follow her on Twitter @adriarwatson.