The Board of Education narrowly voted to hold off on hiring a new chief of staff for the city’s public school district — dealing a temporary setback to the superintendent in her effort to fill a long-vacant role that she has previously described as vital.
Board of Education Secretary Edward Joyner led the way on Monday in encouraging his colleagues to table New Haven Public Schools (NHPS) Supt. Madeline Negrón’s recommendation that Tamesha Webb become district’s new chief of staff.
According to Monday’s personnel report, Webb is a Harvard University graduate with eight years of experience. According to her LinkedIn profile she serves as the Chair of the Governance Commission for the New York State Alliance of Black School Educators and is an adjunct instructor for New Leaders, a New York-based professional-development nonprofit.
The board wound up voting 4-3 on Monday to table the item until the district provides more information about the hiring process to ensure that it has been fair and inclusive of both external and internal candidates.
Joyner and fellow board members Matt Wilcox, Andrea Downer, and OrLando Yarborough III voted in the majority in support of tabling the request. Board members Abie Benitez, Daniel Juarez, and Mayor Justin Elicker voted against tabling the matter.
NHPS has been without a chief of staff for over two years, ever since Michael Finley resigned in July 2024. Finley had been in that role since 2021.
If Webb’s appointment as chief of staff had been approved, she would have stepped into the role on Tuesday at a starting salary of $177,000.
Joyner began Monday’s discussion on the recommendation by raising concerns around resume accuracy, a non-competitive candidate pool, and potentially unfair hiring procedures particularly for internal candidates for the role.
As part of his successful motion to table the item, Joyner asked Negrón to provide the board with the number of candidates that were interviewed for the position and details about the procedures followed to vet candidates, and in particular the “standard verification process” used to ensure a candidate’s resume is accurate.
“In this round of interviews, how many candidates were interviewed?” Joyner asked on Monday during the board’s meeting at King/Robinson School.
Negrón responded that throughout the rolling interview process these past two years, only one candidate was interviewed.
“The idea of interviewing one person for a job is not good practice,” Joyner said. “If you’re not trying to develop the people at multiple layers of the organization then you’re abdicating your responsibilities as a leader.”
Joyner raised concerns that staff members already working for the district might not have been considered for the role. He said that New Haven should continue its past practice of developing talent it has in district. “The state ask superintendents to develop talent for succession and continuity,” he said, while explaining that developing internal talent is necessary for an organizations “succession and continuity.”
He clarified that he is not against hiring external candidates. He cited another hire recommendation on Monday’s personnel report, which the board approved unanimously, for a new supervisor of secondary math.
“That doesn’t mean you don’t bring people from the outside from time to time. In fact, the math candidate is a phenomenal person,” he said Monday. He added the caveat that, before hiring externally, “you should be assured that the person you’re bringing in is better than the people you have.”
Negrón reminded the board on Monday that the chief of staff position has been posted for last two years.
Over the last two years, Negrón said, interview and hiring panels considered roughly four different applicants, including Webb. She said she didn’t bring forward the other candidates for potential hiring because “I do not believe that they meet what I am seeking as described in the job description for the chief of staff.”
She also said applicants are always vetted to be sure they meet job requirements. The standard verification process done by Human Resources includes confirming applicants’ assignments listed on resumes and applications. It also includes the district contacting applicants’ recommenders.
“That has been the rolling process of this position that has been very hard to fill in the last two years,” she said.
The process also includes district cabinet members and the teacher and administrator union presidents being brought into the interviewing step.
“The idea of one person being interviewed where there’s clear evidence that there was no real verification of what the person presented as their experiences is problematic,” Joyner replied.
“How do you start out in a job competition as a finalist?” he asked. “Typically there are multiple applicants. You don’t even start the process until you get multiple applicants.”
Board of Education member Andrea Downer argued for the hiring process to be competitive for the chief of staff role because that position has significant influence over district matters and staff. She said she wants the best candidate selected “from a qualified pool rather than by default.”
Before the board is asked to vote on a chief of staff hire, Downer said she too wants confirmation that internal candidates had opportunities to join the process.
Joyner requested a written report be provided to the board that includes each candidate’s “claimed credentials,” verification of those credentials, and any discrepancies identified with candidate’s explanations for them.
“This is a real problem, a morale problem, and maybe a legal problem if we vote on this tonight,” Joyner concluded. “I know, based on a whole bunch of experience, that this is not going to work out for us if we move forward.”
Board of Education Vice President Matt Wilcox added on Monday that the chief of staff position is “a position that needs to be here.” He said that the number of school administrators in New Haven is below the state’s average. He said that it’s the board’s responsibility to support the district’s superintendent in hiring necessary staff.
“We hire outside people all the time. We hire inside people all the time,” Wilcox said. He also said that, “if it is the will of the board” to request more information to be comfortable to vote, then he will support the request.
Reached for comment Tuesday, Negrón told the Independent in an email that NHPS’ thousands of students, 40-plus buildings, and complex multi-million dollar budget require “relentless operational discipline.”
“When central office departments operate in isolation, projects stall, communication breaks down, and resources get wasted,” she said. “The Chief of Staff is not an extra layer of management. It is our central point of operational accountability.”
The chief of staff role serves as the “connective tissue across all our divisions—finance, operations, academics, and human resources” by chairing the district’s executive leadership team, managing day-to-day administrative coordination, and tracking NHPS’ strategic targets to ensure efficient work.
“Equally important, this position protects my primary focus as Superintendent: staying in our schools, driving academic strategy, supporting our teachers, and focusing on student achievement. By introducing stronger operational oversight at the top, we prevent costly bottlenecks, avoid mismanaged initiatives, and ensure that our central office functions as a lean, responsive support system for our school principals and teachers.”
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