Amy Checkoway is wrapping up six years on the Belmont School Committee, concluding a lifetime involvement in education and town policy that began in high school when she presented a proposal for a student-led curriculum to her local school board.
“I just remember being both really nervous about being in this formal room with all these adults—and there were bright lights, and there were old school TV cameras—but also really recognizing the importance of being part of an important change,” said Checkoway.
Fast-forward to 2019. Her sons were in the third and sixth grades, and Checkoway decided to become directly involved in oversight of the Belmont schools by running for School Committee.
Professionally, Checkoway works in public policy, primarily conducting research and consulting for federal, state, and local government agencies on education systems—with expertise in early childhood education.
“It felt like something that I wanted to try to do, to be helpful,” she said of her decision to run.
Checkoway topped the ticket in a three-way race in April 2019.
Facing Challenges
A year after her election, Belmont was hit by the COVID-19 pandemic, which dominated her first term.
“I think I’ve learned a lot about leadership … what my own leadership style looks like and what [it] looks like during times that are easier, and what it looks like during times that have been incredibly challenging,” Checkoway said.
In April 2021, Checkoway became the School Committee chair. That year, voters rejected an operating override, forcing the committee to make difficult budget choices.
The schools were also continuing to recover from the impact of the pandemic.
“Community members were really struggling, and in some cases really hurting because of the sustained disruptions to our normal way of doing and delivering education,” Checkoway said.
She recalled working with her colleagues to try to repair trust between the School Committee and the Belmont community.
“Although it was really difficult, I was proud of my leadership during that time, which really involved making a lot of space for public comment and questions during our meetings,” she said.
Checkoway added that her efforts also involved communicating with community members outside of meetings, focusing on connecting and building trust with other committee members and town leaders, and trying her best to lead consistently, calmly, and thoughtfully through an unprecedented situation.
“There were so many people who played an important role and led during that time, and I was only one of the many people,” Checkoway said. “But I think it was an important moment, and we were able to turn the corner a bit, going from a very unprecedented, challenging time to trying to come together and figure out our way forward.”
An Evolving Committee
According to Checkoway, her two terms were highlighted by the hiring of Superintendent Jill Geiser, transparency around budgetary challenges, creating a more structured and transparent superintendent evaluation process, and supporting the district’s equity work.
“Honestly, more than anything, trying to be responsive to as many members of the community as possible, which looks like a lot of things, and sometimes looks like just showing up as one can,” she added.
Although she will miss being on the committee, Checkoway said it is well-equipped for the future.
“We have some really strong folks running for the seats that are open to continue to lead the way, and we have district leadership, who I think [are] well-positioned to continue to grow and lead from where they sit in partnership with the School Committee,” she said. “It feels peaceful to move on, from that perspective.”
Moving Forward
Checkoway decided to leave to attend to her work and family. However, she hopes to continue being involved with the town as a Town Meeting member and to be a resource for the School Committee in the future.
“I’ll be cheering things on and helping to support them in a different way—I’m not going anywhere,” she said.
Checkoway said she also hopes the committee will continue to work to stay together through open conversations, prioritize the most pressing issues facing the schools, and remember to appreciate the positive things happening in the schools every day.
“I think [staying together] requires patience,” she added. “It requires open communications—really listening to and trying to trust each other, knowing when to talk, when to listen, being open to community input, trusting our professionals and our leaders and our educators and the expertise that they can add to conversations, [and] collaborating with others.”
