Salutations, Bill.
“That’s all for now."

In the main office of the 100 Building, a tight-knit group of Prep’s administrators recently came together to share their thoughts on Bill Sinfield’s tenure as Head of School. In their testaments below, Cheryl McMillan, Dacia Card, Julie Cook, Laurie Magee, and Laura Fitzpatrick describe the celebrated outgoing chief administrator in their own words and experiences.

Former Assistant Head of School for Upper School Cheryl McMillan, who retired at the end of the school year, notes that “Everyone who meets Bill feels like they’ve known him forever.” With his frank disposition and his lively stories, he’s “like the Mark Twain of headmasters.” Along with his tradition of individually greeting students first thing in the morning as they arrive at school, Cheryl describes Bill as having a “big personality that generates [a sense of] community.”

Dacia Card, Prep’s Business Manager, reflected that Bill is decisive and listens well but prefers to communicate via conversation, not email. (Which is surprising, considering how lucid and emotive his daily and weekly emails come across.) As to his day-to-day demeanor, Dacia has always appreciated that Bill “is not a micro-manager; he trusts his people to do what they are charged to do.” Over the years, Dacia has appreciated Bill’s caring and calming nature. “He puts everyone at ease and makes people feel connected,” traits which were especially important during the last two years. What’s more, during the pandemic and other recent, historical concerns, Dacia remarked that Bill displayed “a unique ability to stay grounded during a crisis.”

The entire group made lists of Bill’s funnier moments and iconic traits during his tenure here. They noted how endearing it was when, in his first few years at Prep, he would study the yearbook religiously to help him remember students’ names. His appreciation of Prep’s student body is renowned, not only in his early morning salutations but in helping students celebrate their birthdays via a classroom visit on their special day.

While it would be considered easy—or even de rigueur—for administrators like Bill to keep an emotional distance, Bill’s communication with families and the community was well-regarded for its sensitivity and openness. He sent daily internal emails to the faculty and staff and, of course, kept the entire extended Prep community abreast of the school’s latest happenings, concerns, and celebrations via his weekly letter. Both email series kick off with well-curated quotes from historical figures and artists.

Bill is also refreshingly unselfconscious. The group had a good laugh, for example, at Bill’s audacious Halloween costumes; they shared a tradition of dressing together as a team every late October. Over the years, he’s dressed as a Care Bear, a mother, a rock star, a COVID Buster (à la Ghostbusters), and as Dru from Despicable Me. He’s good for a laugh at his own expense, in other words. As Bill takes his leave of Prep, the group wanted to remind everyone of his love of fishing, of being a grandfather, and of the reprieve he’d sometimes take in his home garage, sipping on a rum and coke, winding down into a weekend. At school, Bill made his interests known amongst both colleagues and students. Just this past year, he started a speech and debate club with students and involved several parents and staff members in the process. He loves cricket and hockey (as any self-respecting Canadian should), is fond of animals, and outwardly enjoyed substituting in classes and sharing in Quad supervising duties when he could. He’d readily volunteer himself when a faculty member was short-handed.

Per the many scenarios and descriptions everyone shared about Bill, the picture painted is one of the rare administrators who, at Prep, has effectively balanced the line between personal investment and business savvy. It’s as easy to imagine him out on the Quad talking with middle school students as updating the Board of Trustees on the school’s financial trajectory. Julie Cook, Prep’s Director of Development, spoke of Bill’s “intuitive leadership style,” which helped “guide us through the best and worst of times.” And Laura Fitzpatrick, the Assistant Head of School for Enrollment & Advancement, similarly noted that Bill “models caring for oneself” in the hopes of “finding a work-life balance.” He is and has always encouraged faculty, staff, parents, and students to prioritize family, Laura observed. It’s what he embodied day-in and day-out over the last seven years.

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