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Meet the Headmasters

How private school principals see their challenges



Parents often get to know their child’s teachers, but what about the headmaster, the person who sets the tone for a private school? Here’s how a cross-section of private school leaders see their challenges.

Beyond academics

While college readiness might seem to be the chief goal of a private school, headmasters view other priorities as equally important. “My number one responsibility is the safety of our students,” says Michael Gomez, principal of Cristo Rey Philadelphia High School. 

“The ultimate goal that many of the students see is college,” adds Sally Powell, head of school at The Baldwin School in Bryn Mawr, PA. “But their preK-12 piece is one chapter on their long journey, and I want them to enjoy it in the moment, not just constantly be thinking about what’s coming next.”

Shawn Kelly, headmaster of St. Peter’s School in Philadelphia, urges his students to see the larger, global picture. “I want our kids to recognize that there’s no action that we do that doesn’t have a global ramification,” he says.

Day-to-day duties

Beyond educational planning, fund-raising and faculty meetings, headmasters often roam the halls to see students and teachers in action. Rabbi Jeremy Winaker, head of school at Albert Einstein Academy in Wilmington, greets students daily, then joins them for the morning prayer. 

Some headmasters, including Powell and Larry Van Meter, head of school at Moorestown Friends, also teach classes. Powell says teaching differential equations to the seniors offers her added perspective. Van Meter teaches an elective for upper school students “interested in learning how to leverage the values they have absorbed at Moorestown Friends to make them even more effective leaders.” 

Meeting challenges

Baldwin, an all-girls school, must find ways to include boys in their students’ lives. “Especially for middle school girls, we need good ways to engage them, not just around social things, but things that are community service-related or have an intellectual base,” Powell says.

For Cristo Rey, a longer school day and year can tire students and teachers. Keeping them fresh can be a challenge, says Gomez. “They also come with an awful lot of stuff in their invisible backpack — things going on at home, anxiety, stresses and tragic events in their lives. It’s trying to get them to believe they can get through those struggles and excel academically.”

What they wish from parents

Headmasters agree that parents play a large role in their children’s education. For Gomez, it’s about getting their children to do their homework and study at home. “They play a crucial role in the academic success of their students,” he insists. 

Winaker urges parents to better communicate with their children’s teachers. “The more we know from the people who know their child best, the better we can help their child succeed,” he says. “And we often see things in school that the parent might not see because we’re spending a significant part of the day with that child.” 

What they wish from students 

All of the headmasters have something important they wish their students better understood. Students should “be more critical of what they’re looking at” on their electronic devices, urges Kelly. “They need to better evaluate what’s a credible source versus a source that may have other motivations.”

“I wish students better understood that they have a voice,” says Winaker. “If there is something they don’t understand, they should ask a question. If there is something about the school or their educational experience that they think could be improved, or doesn’t seem right, their voice matters.”

Gomez wishes students understood “that every minute at Cristo Rey counts. From the first minute of freshman year, their college readiness is impacted.”

Interacting with the community

As the face of their school, the headmasters’ jobs extend outside the school building and hours. “The other group that’s very important to us is the alumnae,” says Powell, who makes it a point to stay in touch with graduates.

“We are working to help the community understand that we are a non-denominational school with no church affiliation,” says Kelly. “We are much more diverse of a community.”

Adds Van Meter, “An additional challenge for us as a Friends School is to be sure we’re true to Quaker values, while at the same time serving a population that’s 97 percent non-Quaker.” 

Terri Akman is a contributing writer to MetroKids.

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