Seeing Mentoring Through Brooke Cheeseman's Eyes
Every mentoring story begins at one of our school-based Mentor Centers — warm, welcoming rooms where new connections take shape. But for Mentor Facilitator Brooke Cheeseman, who has spent 11 years at Flowery Elementary, these spaces are so much more. They’re where she watches mentoring unfold in real time, often in ways that feel nothing short of magical.
What fascinates Brooke most is the moment a new match begins. It’s two people, often shy and unsure, stepping into something neither has ever experienced before. “It’s a very foreign relationship at first,” she says. “Both the mentor and the mentee are figuring out what this is.” There’s uncertainty on both sides, but also openness — a willingness to try, to be present, and to see what grows.
And then slowly, something remarkable happens. With the right match, hesitation fades. Conversations soften. Comfort settles in. Brooke sees pairs who once sat quietly across from each other begin to laugh, share stories, and slip into a rhythm that feels effortless. “They turn into almost an old married couple,” she says with a smile. “They just get each other.”
What makes this transformation possible, she says, is vulnerability. Mentors step outside their comfort zone and let go of expectations about how the hour should look. Kids step into a space where they can’t hide behind parents or peers and they show up as themselves, sometimes for the very first time. She sees mentors kneeling on the floor making slime even though they’ve never done it before. She sees children bravely sharing the “rose and thorn” of their week because it feels safe to do so. Little by little, they build their own language and their own way of being together.
“We try so hard to create a safe environment,” Brooke says. “There aren’t a lot of safe spaces in the world, so we try to make our Mentor Centers one of them.” And when that safety takes hold, the impact can be profound.
There is one moment Brooke will never forget. Years ago, she brought a fifth grader to meet his mentor for the first time. Later, he told her something that stayed with her: “I just couldn’t believe this person kept showing up for me.” Week after week, that simple consistency became life-changing. Brooke sees this pattern over and over — mentors often don’t realize the depth of the imprint they leave.
From her vantage point, Brooke also sees the ways kids shine in the Mentor Center even on days that are tough elsewhere. She sees adults try again, redirect gently, stay flexible, and return the next week ready to meet their mentee exactly where they are. “Every match is different,” she says. “There’s no perfect handbook. But when both people show up and try — that’s where the magic is.”
About Brooke
Brooke Cheeseman has served as the Mentor Facilitator at Flowery Elementary for 11 years. Before stepping into this role, she was a mentor herself — an experience she describes as “a real bright spot of my week.” That firsthand understanding of what it feels like to build a mentoring relationship from the very beginning now deeply informs how she supports mentors, mentees, and families each day in the Mentor Center.
Brooke lives in Sonoma with her family and has raised her children here. Her former mentee, Jessica, is now an adult, and Brooke has had the rare and meaningful opportunity to watch their relationship evolve over time. “It’s a transition to go from being a mentor to being a friend,” she reflects, “much like what happens as your own child grows into adulthood.” It’s a perspective that gives Brooke a unique appreciation for the lasting impact mentoring can have, long after the weekly meetings end.