The Select Board has decided to hold a second round of interviews with town administrator finalists Nicholas Connors and Jason Silva.

Connors, Silva, and David Williams were interviewed for the Swampscott town administrator position after completing initial screenings with the Town Administrator Search Committee. The search began after former Town Administrator Sean Fitzgerald resigned in late 2024. Although Fitzgerald’s contract was set to expire in June, he agreed to take a paid leave of absence in the final months of his tenure. Department of Public Works Director Gino Cresta has been filling in as interim town administrator since but he did not apply for the full-time position.

“I thought we had three incredible candidates,” Select Board Member David Grishman said. “I still think we could be successful with all three of these candidates.”

Select Board Chair Katie Phelan said she found Connors and Silva “more aligned with personality traits I was looking for and more aligned with what I think the community would be interested in.”

Select Board Vice Chair Doug Thompson agreed, adding that Williams had a “wealth of knowledge” but that it was “a little bit difficult to kind of pull the information out of him.”

“The energy level of engaging and offering things up, just the fact that we didn’t get to questions 10 or 11 with him because the answers were a little bit harder I felt to pull out,” Thompson said. 

Select Board Member Danielle Leonard said the group has a “whole wealth of things we have to look at.”

“Obviously we have to look at experience. We have to look at education, but for me a big part of this comes down to a personality that matches what Swampscott needs at this given moment,” Leonard said. “I feel like a big part of what we need is someone that can facilitate, be a leader but also listen to residents and begin the healing process in trying to get this town in unison on the right path forward.”

Select Board Member Mary Ellen Fletcher was the one board member who put Williams in her top choices, saying she “really enjoyed Mr. Williams’ financial perspective of everything.”

“I thought that he’s really clear on what his role is. His role is to get the job done, follow what the Select Board’s goals and priorities are,” Fletcher said. “I decided that I had to get it down to two and that was a very, very hard decision for me because I really did like Mr. Connors. His personality was engaging and fun, however the fact that he is not negotiating contracts, I just feel like he is early in his career. I think we need someone at the next step, someone who’s always been in this position, knows the ins and outs, knows what happens in the state.”

Fletcher noted that the board only had one hour to interview candidates for a position of significant responsibility. Agreeing with Fletcher, Leonard, who works in human resources, suggested that the group may want to extend the interviews for another week.

“I’m used to seeing multiple rounds of interviews for something like this,” Leonard said. “I have reservations about making a decision of this magnitude with just an hour each, and while I do feel great about both of them and I’m ecstatic about the candidates, I want to make sure that we have left no stone unturned…I do want to be thoughtful about how we approach this next step, and I’m not sure that we can make a snap decision.”

Leonard also encouraged residents to share their feedback with Select Board members after watching the interviews.

“Certainly the five of us, it’s our decision, but we’re making a decision for 15,000,” Leonard said, adding that it’s the board’s “obligation” to hear other opinions.

Phelan added that extending the process would help ensure fairness to Connors and Silva, who were interviewed a week apart during the first round with the Select Board.

Consultant Rick White said it is not unusual for Select Boards to go through a second round of interviews before choosing a town administrator. 

Connors and Silva will be asked to return on Monday for additional interviews, and the Select Board will make a decision then. The board did also raise other dates if needed, but they prefer that both Connors and Silva are interviewed consecutively and that it is done by the end of next week.

The Select Board will discuss who they are in favor of publicly. An executive session, however, will be used to discuss negotiations related to salaries and other items that might be a detriment if it was publicly discussed, according to Phelan.