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Two weeks after his motion to keep Christopher Senior as town manager died for lack of a second, Vice Chair William McGonigle made the same motion again Aug. 24 — and this time Michelle Prior seconded it.
The Winchester Select Board then voted 4-0 by roll call to exercise the one-year renewal option in Senior’s employment agreement, keeping him through Dec. 31, 2027. Chair Anthea Brady, McGonigle, Prior and Michael Bettencourt all voted yes.
Nothing in the contract changed between the two meetings. What changed was that the board had worked through the argument over goals and process that stopped it Aug. 10.
What the contract required
Senior signed the agreement Jan. 9. It runs Jan. 14 through Dec. 31 and carries an option for 2027.
The option depends on an evaluation completed no later than Sept. 30 that produces at least a satisfactory overall rating and majority support on the board. If the board fails to complete a good-faith review by that date, Senior can exercise the option himself with written notice by Oct. 15.
Brady said the contract standard was an average of 3 in each section plus a majority of members voting to continue.
Senior’s ranking results, filed with the Aug. 24 packet, show seven overall ratings: 3.4 for board support/coordination; 3.8 for leadership/staff effectiveness; 3.3 for planning and organizing; 3.6 for communication/community relations; 3.4 for problem solving and decision making; 3.8 for budget/financial management; and 4.1 for personal, professional and organizational integrity.
The completed forms recorded five responses in favor of exercising the renewal option.
McGonigle moved to renew on those numbers Aug. 10. No one seconded, and the official record says the matter was held to the next meeting, not rejected.
Prior said she wanted Senior’s goals, his self-assessment and a proposed set of new goals in one packet before voting; Bettencourt supported the two-week wait.
McGonigle said the two were not following through on a signed contractual agreement, the record says. Prior said her position on the renewal itself had not changed.
Senior broke in to ask the board to “take the temperature down a few degrees.”
Renewal raises his pay 2.5%, or $5,750 on the $230,000 he earns in 2026, to $235,750 next year.
Strong marks, and a list of fixes
The comments were not a clean sweep. Board members credited Senior with learning Town Hall operations quickly, recruiting well, keeping staff feeling supported and building an alternative budget after the override failed.
They also asked for more comprehensive written analysis, clearer recommendations with pros and cons, better organized board materials, stronger follow-through and more accountability for staff performance.
The lowest individual score, 2.8, was for presenting ideas and plans in a clear, concise and persuasive manner. Follow-through on implementing decisions, multiyear budget planning and labor negotiations each drew a 3.
Prior pressed one item in person: the management dashboard she said she asked for in February and March. The unbilled Eversource charges that surfaced earlier in the meeting, she said, were the kind of surprise she would rather see coming.
Bettencourt said residents tell him requests vanish.
“There’s just kind of a black hole where requests go in,” he said, and no response comes back — from the Select Board or from management.
McGonigle put it personally.
“I don’t really like how we got you, Chris, but I am very happy that we did,” he said.
He told Senior that Winchester is benefiting from Cohasset’s loss. Senior spent 12 years as town manager there.
Goals vote pushed to Sept. 14
Senior is Winchester’s first permanent town manager since Beth Rudolph left Sept. 3, 2025. He took the oath Jan. 14 after a search in which two of three finalists withdrew.
The Select Board voted Dec. 22 for a contract whose second year turned on a performance review rather than an unconditional multiyear term.
Brady said the board will take up Senior’s goals — adopted March 2 and updated July 10 — at its Sept. 14 meeting, and proposed quarterly check-ins in October, January and April around the July review.
She said Comptroller Stacie Ward, the board’s other direct hire, also needs a formal evaluation process before the end of the calendar year.
Bettencourt said one-year deals are not the best arrangement for a town’s chief executive, and both he and McGonigle said they would discuss a longer term in executive session.
Senior said the vote lets him move on internal changes.
“One of the things that I can now formalize a little bit more is a little bit of reorganization,” he said.
His July update to the board says he has more than 20 direct reports and wants a structure closer to eight, and that he will ask fall Town Meeting to fund a unified electronic permitting system.
Will Dowd is a Massachusetts journalist who covers municipal government and community life for Winchester News. He is also the founder and editor of The Marblehead Independent, a reader-funded digital newsroom.
