Alumni in Education

Darian Reid: The Tools for Leading Change

Steppingstone 1999 / Roxbury Latin School 2005 / Bowdoin College 2009 / St. John’s College Graduate Institute 2017


“Culture is everything we do from the moment the school day begins,” reflects veteran educator Darian Reid. As he discusses his new leadership role as Director of Community and Culture at the Roxbury Latin School, he quickly adds, “I take the culture piece seriously.”

Seriously. It’s a word that he doesn’t use lightly. He’ll hear others say that they never take themselves too seriously. “I take this life and this work very seriously,” he explains.

Since joining Roxbury Latin’s faculty a decade ago, Darian “has distinguished himself as an exemplary teacher, class master, coach, and advisor,” the school noted in announcing the news in July. At a time when schools nationwide are heeding calls for elevating the work of diversity, equity, and inclusion, the creation of the new position reflects the seriousness of the school’s commitment to that essential goal.

Darian will take the lead in a number of ongoing efforts, including enhancing professional development and “evolving the curriculum so that all students recognize themselves within it.” As he notes, he’s already been doing pieces of the work unofficially while serving as assistant dean of students and teaching as the John P. Brennan Chair in Classics at his alma mater.

His new role takes advantage of everything in “my toolkit,” he adds. He brings empathy. He’s a communicator and a listener. He’s passionate about his own learning, most recently through his studies in the Klingenstein Center’s Private School Leadership program at Teachers College, from which he expects to graduate next spring. Realizing “I don’t have all the answers,” he believes in leveraging the talent around him. Having worked within many realms of school life adds both credibility and a lens through which to see needs and opportunities.

What challenges does Darian see ahead for schools, “In a word, change.”

Importantly, he also brings a sense of what it means to approach work in an authentic way.

As he ponders that point, he recalls an experience as a summer intern at Steppingstone. How do you “walk the walk?” That was the theme-based question of the day, and he joined Scholars in personally reflecting on it. “My answer was by being myself,” he says.

To Darian, “school is about relationships first.” As the years go on, “I’m far more intentional about building relationships with students,” he adds. “When students sense you care, they’ll want to learn and do their best.” He still remembers his elementary teacher who suggested Steppingstone to him, caring enough to see and recognize his nature and his talents.

In a sense, his new leadership role “brings me back to what got me in the game in the first place,” he says. As a high school senior, he first caught a glimpse of the difference that he could make as a teacher. Volunteering in a Roxbury preschool, he was assigned to teach kids to write their names. He also asked them to stretch and see how much more they were capable of learning. “You’re teaching and they’re getting it!”

It’s one of his life’s epiphanies.

In the game of teaching, pressure comes with the territory. You’ll have moments to learn from. Now as then, “you have moments when you can see it in their eyes.”

What challenges does he see ahead for schools? “In a word, change,” he says. “Change is not easy for anyone.” With the pandemic, “we’ve seen how a change in the rhythm of school has unsettled people. Even if a change is necessary, it doesn’t mean it can happen easily.”

Whatever the challenges, the possibilities excite him. At Roxbury Latin, “I have our mission as my anchor, and I believe in our values,” he says. And the work aligns with his own values.

At his core, he’s “never satisfied.” It’s no time to be.