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He’s Prep’s new Dean of Students, but he could tack onto his title another area of expertise: Kindness.

Brian Tregembo is starting his 24th year at Prep determined to strengthen and expand the school’s culture of kindness, which he was instrumental in establishing.

“T,” as he’s known, made sure Prep was among the nation’s first schools to join Harvard University’s “Making Caring Common” campaign and worked over the years to establish various student groups to promote inclusivity and positivity.

Unfortunately, COVID undermined some of those efforts and has had “some real lingering effects” on Prep students’ confidence and mental health, he says. Remote learning, isolation, and navigating the normal issues of adolescence have been all students could handle in recent years.

“After COVID, our kids are struggling with being kind to themselves,” Tregembo explains.

For instance, last year, he worked with students in his advisory on asking for help. “We talked about what happens when you ask for help, why don’t you ask for help. Some of the things they said were mind blowing: ‘I’m never going to ask for help because I don’t want anyone to know I’m struggling.’ There’s low esteem among our kids where you wouldn’t expect it,” he says.

That makes Tregembo even more determined to rebuild a culture where being kind to one another is simply the norm that radiates out to the community at large. “The idea of helping people is super important to our kids,” he explains. “Building everything on relationships includes building relationships with the community.”

Educating students about diversity, justice, inclusion, and other issues through affinity groups, curriculum, language, self-work, and other approaches makes it easier for them to understand and accept one another, Tregembo says. The idea is to establish a community where shaming, bullying, or excluding anyone for any reason is unacceptable.

“That’s not how we do things here” is a phrase he wants students and faculty to adapt. “That idea of kindness is how we’re going to come together,” he says. “This is just as important as all the other things we do.”

There’s “a minefield of things” students and faculty must navigate to reach common ground, and not everyone will be happy no matter what approach is used. “No matter what you do, someone’s going to be mad about it,” Tregembo says. “But,” he adds, “it’s hard to be mad about being kinder to each other.”

Tregembo brings a wealth of experience to his new role. He started at Prep in 2000 as a basketball coach, then worked SummerPrep, became a substitute teacher, and finally got hired full time as an English teacher. He’s taught every grade from 6-12, was the seventh- and eighth-grade coordinator for seven years and the ninth-grade sponsor for four years. “I think I’ve been on more committees than anyone,” he says with a laugh.

Tregembo will continue to teach his Intensive Writing Workshop course at Prep.

He and his wife Venessa have two sons: Jaxon ’22 and Ryder ’26.

As he embarks on this new adventure, Tregembo can look around campus and see physical evidence of the groundwork he helped lay: Stickers he distributed that say, “Dude, be nice.” It’s a mantra he hopes Prep will embrace.