Across Milton, underclassmen struggle with learning the curriculum itself and how to work and balance that work throughout the school year. The strain only intensifies with a varsity sport, pressuring younger students to hold their own and maintain a massive commitment throughout the season, exam weeks, large assignments, and their daily homework load. In response, the Academic Skills Center has recently broadened its horizons, implementing a new mentorship program into the Athletics Department. Lainey Sloman and Kelsey Mumford from the Academic Skills Center quickly recognized the strain’s effects on underclassmen through patterns reflected in grades and feedback. “One pattern we observe for class four students over the past couple of years is that Class IV students who play a varsity sport tend to experience more academic struggles,” Sloman reports, explaining how the Skills Center “thought that it could be helpful to support those students in navigating that experience, and the best support would be people who would have gone through it.”
Mumford and Sloman hand-picked mentors through the Academic Skills Center connections to properly represent the program, keeping in mind their commitment to the role. They ensure that a few upperclassmen on each varsity team take on the mentor role, with each mentor implementing the dynamic into their specific team. Selections were overall successful, in the analysis of soccer Mentor Jacob Matalon ’26, who says, “Max and I really cared about helping [mentees] adapt to high school, socially, athletically and academically.”
“The cool thing,” says Sloman, “is that we’ve taken things that mentors have created and brought them to mentors in the following seasons as advice and sort of best practices.” Those activities include a wide range of possibilities including the cross-countries buddy runs, warmup activities across all sports, and drives to team dinners. As the program progresses even more, many reveal their prior awareness of the difficulties, and how the role of mentor allowed them to personally address those; Swim Mentor Kat Ifill ’26 for example, recognizes, “swimming is so physically and mentally challenging, that was something I felt was very important to implement as my role as a mentor.”
Due to the different circumstances of each sport, each mentor fills their role as they see fit, whether that be constant activities and outreach or just a known source to talk to. Mentor Jocelyn Riordan ’27 compared her experience across two different seasons: “for squash, our team's a little bit bigger, whereas for tennis, obviously, our students is a little bit smaller, and it's been easier to have a bit more of a bond, so it's been, I would say, a little more effective to be able to communicate with a freshman and build closer and tighter bonds.”
Mentors found success in strengthening natural areas of bonding and fitting the team with solutions to the best of their ability. Soccer Mentor Matalon revealed the behind-the-scenes as a mentor, noticing the struggles underclassmen were experiencing early in the school year. He and his fellow mentor “came up with weekly check-ins with our freshman teammates about the progress they have been making or perhaps a challenging situation they are still in,” and after evaluation, they worked to “help them understand the many resources on campus, such as Extra Help Blocks and the Academic Skills Center.”
Underclassmen across different teams found the most effective bonding came naturally. Golfer Riley Donovan ’29 valued the mentorship that would happen on bus rides: “you know, we have long commutes to all the [games], so you kind of get to know the upperclassmen,” while wrestler Ben Koslowsky ’29 found mentorship from the unlikely source of his opponents: “I'm wrestling a lot of the older kids, so it's probably helpful.”
Sloman and Mumford have already heard from mentors that “it’s in some ways really shifted team culture positively.” Squash and tennis mentor Riordan said that upperclassmen “are able to be more present in the team if they feel like they're being supported more.”