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Town Administrator Candidate Interview Follow Up Questions (Link: 00:00:00 – 01:02:00)
The Select Board conducted follow-up interviews with the two remaining candidates for Town Administrator. Chair Katie Phelan opened the meeting, noting they were being recorded, and began with Nick Connors as the first candidate.
Leonard asked Connors about his career moves, specifically why he was looking to leave Milton after recently acquiring the position. Connors explained he saw this as a tremendous opportunity and natural career progression, which he had discussed with Milton Town Administrator Nick Milano from his first day. He emphasized this was not about firing out resumes everywhere, but rather a specific opportunity with generational challenges in Swampscott. When Leonard probed about his conversation with Milano, Connors said Milano was excited for him and supportive, texting good luck before the interview.
Leonard followed up asking what made Swampscott the right long-term fit and why the board should feel confident in his commitment. Connors cited his 30-year affinity for Swampscott dating back to high school, comparing it favorably to his hometown of Stoneham. He highlighted generational opportunities like the Hawthorne property and economic redevelopment decisions, emphasizing his public engagement and communications experience from DCR and DOER would align well with the town’s needs for community input on major decisions.
Grishman asked for specific examples of similar experiences at DOER or DCR. Connors detailed his public engagement work with communities hosting DCR properties, including infrastructure projects and facility development that required community input. He described innovative approaches like using Instagram for playground design input in South Boston and mentioned new tools like Google’s AI that can convert dense PDFs into accessible podcast-style discussions. He used Swampscott’s 107-page financial policies as an example, saying he tested the tool and it created a 30-minute podcast explaining the content in natural language.
Thompson asked about management style, both for prioritization and creating a great workplace. Connors said prioritization comes from the Select Board’s direction, with the Town Administrator executing their goals and priorities. For creating a great workplace, he emphasized the importance of human resources issues as top priority, having conversations with all staff including department heads and informal leaders, understanding what motivates individuals, and trying to align their interests with board objectives. He stressed the importance of building relationships and understanding what’s happening in employees’ lives.
Fletcher asked how he would handle a department with poor morale. Connors said he would start by talking to both the department head and individual staff members to understand the concerns driving low morale, emphasizing that listening and learning from staff is essential rather than simply dictating improvements.
Phelan asked about the differences between municipal leadership roles like Town Administrator, Town Manager, and elected Mayor. Connors explained that mayors make both policy and operational decisions, while Town Administrators and Town Managers vary in strength depending on the town, with differences in appointment authorities. He characterized Swampscott’s TA role as weaker, where he would prepare information for the Select Board to make informed policy decisions rather than making policy himself. He emphasized providing data plus impact analysis and execution plans so decisions aren’t made in a vacuum.
Fletcher asked about balancing next year’s budget without tapping unused levy capacity. Connors said he couldn’t answer definitively without knowing health care costs and special education/out-of-district transportation costs, which are the biggest budget drivers and difficult to forecast. He mentioned these costs exceeded initial projections in his current role and emphasized the importance of understanding the Select Board’s priorities before making budget recommendations. He suggested tools like working with Cook & Co. to analyze insurance options.
Grishman asked about Connors’ feelings on an underride. Connors said if the community wanted to pursue it, town staff would need to operate under those constraints, but noted that unused levy capacity provides flexibility for changing financial conditions. He emphasized his role would be providing information for informed decisions rather than giving personal opinions on tax policy. He described building a website in Milton showing actual tax bill impacts for residents and communicating budget issues early and transparently throughout the year.
Thompson asked about Connors’ level of financial responsibility in previous positions. Connors clarified he was part of the strategic team in Milton working with finance staff on forecasts and decisions, while at DOER and DCR he managed the financial process with existing finance staff. He mentioned working with mentor Andrew Flanagan from Andover to refine budget processes and would work closely with department heads on budget preparation in Swampscott.
Connors concluded by providing additional context about collective bargaining, clarifying that while he hadn’t run the process directly, he had a philosophy of building trust and relationships in advance, ensuring financial constraints are clear to bargaining partners, and focusing negotiations on retaining and fairly compensating existing employees. He mentioned his experience as second-in-command in Milton doing comparisons, strategy, and participating in negotiations.
The board then interviewed Jason Silva as the second candidate. Leonard asked about his decision to leave Marblehead. Silva said he was “cooked” and needed a break from municipal government for his physical and mental health and family, despite having just signed a new five-year contract. He always knew he’d return to municipal government eventually.
Leonard asked what made Silva think Swampscott would be different from Marblehead and why they should feel confident in his commitment given his recent contract renewal in Dunstable. Silva acknowledged he didn’t know if it would be different but said he was in a much better place now, having rediscovered his joy and passion for the work. He said he wouldn’t have applied unless he thought it was a good fit where he could make meaningful impact. Regarding commitment, he expressed wanting a more stable, long-term position, noting he was grayer now and had varied experience but wanted to settle down.
Thompson asked about Silva’s management style regarding prioritization and creating a great workplace. Silva described himself as a “big list guy” who constantly prioritizes based on goals and objectives developed with the Select Board. For workplace culture, he emphasized valuing and supporting people, earning trust, tying everyone’s work back to organizational goals, recognizing good work, providing constant feedback, maintaining an open door policy, transparent communication, and celebrating wins. He mentioned implementing a peer-to-peer recognition program and starting staff meetings with TED Talks, often using Boston Celtics examples to discuss leadership and teamwork.
Fletcher asked how Silva would manage a department with poor morale. Silva said he would work with the department head to understand the issues, share feedback, coach them up, and involve HR if necessary. He would respect the department head’s role while being willing to get involved if needed, emphasizing his passion for workplace morale due to its impact on organizational productivity.
Leonard asked what would happen if the department head was the problem. Silva said that would become apparent quickly when working with and coaching the department head. He emphasized being authentic and not force-feeding solutions, but if the department head wasn’t being effective, he would step in to help with the situation and provide coaching.
Phelan asked about differences between municipal leadership roles and Silva’s approach to the TA position in Swampscott. Silva said he learned the differences on the fly, noting city government is more nimble while town government involves longer processes with more buy-in, often resulting in better outcomes. He sees the TA role as providing recommendations when warranted but understanding the Select Board makes the decisions, executing their goals within set parameters, and ensuring board members stay informed about significant issues. He emphasized viewing the role as a collaboration and partnership.
Fletcher asked how Silva would balance next year’s budget without tapping unused levy capacity. Silva said it would require tough decisions that some people may like and others may not. He described learning to put budgets together in Dunstable, characterizing it as “money in, money out” that must balance. He emphasized creating a process people buy into, communicating parameters clearly, and weighing options after receiving budget requests.
Grishman asked about Silva’s feelings on an underride. Silva said these are community decisions, referencing his experience with three override requests where he made recommendations but emphasized the community ultimately decides. He said if the community wanted an underride and prioritized that over municipal services, his job would be to implement that decision.
Fletcher asked about the challenge of working with override votes when the school budget involves another community. Silva described the complex process in Dunstable with the Groton-Dunstable Regional School District, where Dunstable pays 23% of costs. He created a budget working group including finance committees, select boards, school officials from both towns, and himself. After failed override attempts, they implemented extensive community outreach including kitchen conversations, coffee meetings, social media campaigns, forums, and workshops. When overrides failed, cuts were made to municipal services the first year and school positions the second year, with the community understanding the consequences due to transparent communication throughout the process.
Phelan asked who handled the communications work. Silva said he did most of the budget communications work with help from an assistant to the town administrator who is skilled at social media. He noted they built the town’s social media presence from nothing, which had significant impact and community appreciation.
Silva concluded by thanking the board for the opportunity and noting he knew they were conducting due diligence since he’d heard from many friends. He wished the board and community luck regardless of their decision.
Town Administrator Candidate Selection Discussion and Vote (Link: 01:02:00 – 01:47:00)
Thompson suggested the board vote on the candidates, but Chair Katie Phelan noted they would not have public comments and would proceed to discussion of the finalists. Fletcher asked for transparency regarding any communication board members had with either candidate. Thompson, Phelan, and Grishman reported no communication. Thompson mentioned receiving outreach from one candidate but did not respond. Fletcher reported the same situation as Thompson.
Thompson stated both candidates were terrific and the decision became harder rather than easier. He requested a five-minute break to process the information before making comments. Phelan agreed to a ten-minute recess, noting board members would not discuss amongst themselves during the break.
After the break, Fletcher began the discussion, noting both candidates performed well again. She explained that Silva’s service in Marblehead during COVID and serious deficit situations made him more vulnerable to public criticism. Fletcher conducted extensive due diligence, speaking with residents in Marblehead, Senator Lovely’s office, three Select Board members, and department heads, receiving mostly positive reviews with one mediocre review from a safety department head. She was leaning toward Silva based on his experience, stating that if both candidates were equal, experience would be the deciding factor, but she believed Silva had more comprehensive experience.
Leonard acknowledged the difficult decision and emphasized relying more on candidate responses than reference checks, which she considered subjective. She was leaning toward Connors, citing concerns about Silva’s Marblehead experience and preferring a candidate without potential negative connotations. Leonard was impressed by Connors’ due diligence about Swampscott, his understanding of town priorities and pressing issues. She noted Connors’ eagerness to be a Town Administrator with a fresh perspective, his law degree, and state-level experience at the Department of Environmental Protection and DCR, which function similarly to small municipalities. Leonard emphasized the importance of communication skills and relationship repair with residents and staff.
Grishman described the difficult decision between two incredibly talented candidates who could both be successful. He praised Connors’ preparation and thoroughness in both interview rounds, noting his hunger and anticipatory responses to questions. Grishman acknowledged Silva’s proven ability to run municipalities, his variety of experience, and state-level connections. He emphasized the importance of having someone who has demonstrated they can manage a municipality, appreciating Silva’s diverse roles including finance director and chief of staff. Given Silva’s experience, Grishman was leaning toward him.
Thompson expressed satisfaction with either candidate but highlighted Silva’s workplace culture answer, particularly the commitment demonstrated by using Boston Celtics videos in staff meetings. He noted Silva’s deep learning from past experiences and specific examples of community engagement including kitchen conversations and cafe talks. Thompson appreciated Silva’s financial expertise and experience, while acknowledging Connors’ excellent communication skills and innovative ideas about AI and community engagement. He concluded he would probably choose Silva but would be happy either way.
Phelan described Connors as “fresh” and noted his preparation, vulnerability, and genuine desire for the position. She identified the main community feedback areas as transparency, communication, and finances, noting that ideally one candidate would excel in all areas. Phelan saw Connors as stronger in communications and transparency due to his fresh outlook and community engagement experience, while Silva was stronger in finances and budget experience. She argued that financial skills could be more easily learned than communication skills, and believed Connors’ state-level work provided adequate financial background. Phelan appreciated Silva’s vulnerable explanation of his Marblehead departure but was leaning toward Connors.
Leonard raised concerns about Silva’s pattern of moving between municipalities for short periods, noting his recent contract renewal in Dunstable but applications for other Town Administrator positions. She questioned whether Swampscott would be his long-term stop, citing his three-year stint in Marblehead and two-year tenure in Dunstable. Leonard worried about investing time, effort, and money in someone who might not stay long-term, especially given Silva’s admission that he was “cooked” after his Marblehead experience. She expressed concern about how Silva would handle Swampscott’s high-pressure environment given his previous experience in a similar neighboring town.
Thompson acknowledged the preference to avoid a 3-2 vote and offered a different interpretation of the candidates’ backgrounds. He noted that unique challenging situations like Marblehead’s pandemic and financial crisis were low probability events, and that Silva’s willingness to continue as Town Administrator after six years of experience demonstrated commitment to the role. Thompson contrasted this with Connors’ year and a half as assistant Town Administrator, viewing both candidates’ motivations as potentially positive rather than concerning.
Fletcher defended Silva’s decision to prioritize his health and family during Marblehead’s challenging financial situation, noting that Connors also had a pattern of job changes with tenures of one and a half years, one year, and three years in previous positions. She emphasized that career moves are common and that Silva’s response to recruitment calls was understandable.
Thompson clarified the process, confirming they needed to make a public vote for their first choice candidate to begin negotiations. Phelan explained that while she preferred consensus, she wouldn’t force a 3-2 vote if the board’s will favored one candidate. She noted they were fortunate to have a strong second candidate and that salary negotiations would occur in executive session.
Fletcher made a motion to select Jason Silva as the first candidate and Nicholas Connors as the second candidate. Grishman seconded the motion. In a roll call vote, Fletcher, Thompson, and Grishman voted in favor, while Leonard voted against. Phelan voted in favor “with great regret,” making the final vote 4-1 in favor of Silva as the first candidate.
The board then moved to adjourn the public meeting to enter executive session for contractual discussions, with plans to contact the candidates following those negotiations.
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