Winchester town manager Chris Senior discusses failed override, staffing and outreach plans

Chris Senior, Winchester’s town manager, said the town will need to keep discussing a possible future override while pursuing other revenue and staffing adjustments after the recent ballot question failed.

“There's going to be a need to have another conversation about an override,” Senior said in a May 21 interview on the Winchester Beat podcast. He described the recent town meeting as “an open conversation” that produced a unanimously adopted operating budget with “no amendments” on the floor, crediting the finance committee and town staff for their work.

Senior, who took office Jan. 14 and previously served 12 years as town manager in Cohasset, framed his first months in Winchester around listening, learning and engaging with residents and local boards. He said his role is to manage day-to-day municipal operations — public works, police, fire, water and sewer, permitting and other services — and to execute the priorities set by Winchester’s Select Board and town meeting.

“I’m not the mayor. I’m not elected. I don’t take political positions,” Senior said, describing the town manager role as operational rather than political.

Why the override failed and what comes next

Senior said the override placed on the ballot by the Select Board was the result of careful deliberation, but voters rejected it. He said the campaign and the winter spike in costs made timing difficult for some voters.

“People want high services. They want high quality, and I think there was a lot of uncertainty” between February and March, he said, noting higher energy and commodity costs affected municipal finances.

He emphasized the town continues to have a sound fiscal foundation despite the failed question and the hard choices made, including freezes and cuts. Senior said some positions were frozen or restructured to generate savings and that the town is evaluating which hires are essential as it moves forward.

Staffing and hiring approach

Asked about a retired assistant town manager role, Senior confirmed the position has not been refilled. He said interim and part-time contractors are covering work such as the compensation and classification study and capital planning, and that he is considering a restructured leadership position that might combine responsibilities rather than restoring the previous job description exactly.

“The money’s budgeted,” he said of some positions, but added the town is proceeding on a case-by‑case basis and expects some savings from temporarily holding roles open.

Senior also identified the departments with the largest staffing levels: public works (just under 100 employees), fire and police (including part‑time crossing guards), while noting many other town functions have small staffs (for example, three positions in the assessor’s office). He said there is no significant “bloat” and that employees are actively working across functions.

Revenue constraints and state aid

Senior outlined Winchester’s limited local revenue levers: property tax remains the dominant revenue source, and the town collects modest amounts from a local meals tax, motor vehicle excise taxes and a recently adopted lodging tax tied to short-term rentals. He said these sources are small relative to the town’s needs.

He called for greater state flexibility to give municipalities more tools, noting state deliberations over school and municipal aid (chapter 70 and unrestricted local aid) and a governor proposal that would modestly raise the local meals tax rate. “Even a quarter percent” change in local-option tax rates, he said, could yield material dollars for the town.

Communications and community outreach

Improving how the town communicates with residents is a priority, Senior said. He described plans to reorganize staff time to support more regular social-media updates, a refreshed town website and short how‑to videos explaining permits and services. Senior also said the town manager’s office merged its mailing list with the clerk’s database to expand newsletter reach and promoted the town’s alert feature for committee agendas and meeting notices.

“We need to make sure the website’s updated regularly,” Senior said, adding that he wants to meet residents in public places and use multiple channels — social media, flyers and short videos — to reach different audiences.

A personal note and tone for town politics

In a closing, lighter segment, Senior described walking his golden retriever, Kayla, around Winchester and stressed civility in local debates.

“Be respectful,” he said. “People are in this town because they love it. You don't have to agree on everything… But treat each other respectfully.”

What’s next

Senior said the town will continue operational planning over the summer, fill some vacancies only when necessary, and prepare for further conversations about the town’s fiscal path. He signaled a pragmatic, iterative approach: adapting roles, tightening operations where needed and improving outreach while preserving core services.

The remarks appeared in a Winchester Beat podcast episode recorded May 21. For more details on items Senior discussed — including staffing counts, the compensation study and the town’s capital planning — Senior said residents can sign up for town alerts and newsletters on Winchester’s website.