Boston Public Schools needs to find a new permanent superintendent after Tommy Chang’s abrupt departure last month. Observers predict there will be plenty of people interested in the job, since it is a high-profile gig.

“Jobs like the superintendency in Boston are typically very sought-after positions,” said Michael Casserly, the executive director of the Council of the Great City Schools, which represents large urban districts. “They are considered pinnacle jobs in elementary and secondary education. People of talent and passion and commitment are attracted to these positions.”

But, Casserly added, there aren’t many “really highly-skilled people around” who can successfully run a district like Boston.

Observers in and out of Boston said they worry the city won’t be able to recruit high-quality candidates who can pull the district forward. Longstanding challenges and new problems stemming from Chang’s departure will likely scare away strong applicants, according to some people watching the district.

“This is going to be tough,” predicted Stuart Berger, an education consultant and retired superintendent. “I could be wrong, and Princess Charming could be out there. But this is going to be tough. Very tough.”

Experience Matters
Chang came to the district three years ago having never run a district.

“That was his fatal flaw,” said Richard Stutman, a former president of the Boston Teachers Union.

Chang was making progress towards improving the quality of teaching and opportunities for black and Latino students, who make up the majority of the enrollment. But he struggled with managing operations and communicating with parents. He scrapped a plan last year to change school start times after some parents revolted and Mayor Marty Walsh distanced himself from the idea.

“This is partially a systems failure,” said Paul Reville, a Harvard education professor and former Massachusetts secretary of education. The school committee, mayor and superintendent were not “on the same clear page,” he added, and Chang’s inexperience didn’t help.

Boston needs better candidates for the job, a “deeper pool with more successful experienced frontline leaders,” Reville said.

Temporary Or Permanent?
Several problems may discourage experienced candidates from applying for the job.

It’s not clear why Chang was forced to resign, and that may give some candidates pause, said people who have participated in such searches before.

A second and bigger challenge could be the interim superintendent appointed by Walsh, and unanimously approved by the Boston School Committee. Earlier this month, Laura Perille, the former CEO of EdVestors, a 15-person nonprofit investing in Boston schools, accepted the job of running the district temporarily.

During that same meeting, school committee member Miren Uriarte openly worried that Perille would stay on permanently. Perille has said she’s “solely focused” on the interim job, but outsiders urge the district and city to make it clear that she’s barred from applying.

“Otherwise other people will say, 'Why should I apply?'” education advocate John Mudd said.

The third problem is the way the job is structured. Boston’s superintendent technically reports to the school committee, but the mayor appoints the school committee and in practice, calls the shots. Boston’s schools depend on city hall for their funding. As Berger said, when a mayor is in charge, and you don’t have the power to give teachers a raise, “you’re basically the assistant superintendent.”

The mayor, however, can give a superintendent room to maneuver. “The mayor has got to understand that he can’t run the school system from city hall. That he needs to get a strong leader in the school district and support him or her,” Mudd said.

Too Much Sunlight?
The last problem comes from the state. Its sunshine laws require that school districts publish the list of finalists for the job.

"You’re pretty much not going to get a superintendent who’s not in trouble if you’re releasing the names,” said Berger, who ran several districts around the country for more than 20 years and now coaches aspiring district leaders. He suggested that transparency might be Boston’s biggest obstacle.

Reville agreed: “Sitting superintendents who are highly successful and have the support of their school boards and communities are reluctant to advertise that they’re looking for another position, because it will undermine their support in their home communities.”

Reville recommended that the state create waivers to the open meeting laws so mayors or school districts can directly appoint a superintendent. Parents, school advocates, and journalists wouldn’t like it, Reville and Berger noted, but it may be one of the only ways Boston can land a talented, experienced leader.

Correction: This story has been updated to reflect that Boston's school superintendent officially reports to the school committee.

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