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According to Bessie Speers, if someone spent a half-hour sitting in the entrance hall of any school in America, he or she would be able to discern the school’s personality. Are the students loud and carefree? Do they tiptoe about, hardly making a sound? How are they dressed? What do they talk about? It won’t take long to find out.
As Tower Hill School nears its centennial in 2019, Speers is not interested in changing the school’s character. Much of what it is—and has been—drew her to the head of school post: integrity, warmth, humility, ambition and camaraderie. “We matched up nicely,” she says.
As Tower Hill’s first-ever female leader, Speers is quite aware of her place in the school’s history. But she’s far more concerned with her role in shaping the future, rather than dwelling on something that might have been a long-term point of conversation decades ago but is now a sensible move in an extremely modern educational marketplace. “At this point, it’s really a non-issue,” says Speers.
So is her replacing Christopher Wheeler, who in October 2013 was arrested on charges of possessing child pornography and was sentenced to 50 years in prison in 2015. Though the Delaware State Supreme Court overturned the conviction in March, citing improperly broad search warrants, the incident wounded Tower Hill. It’s up to Speers to help the school move on, and she has embraced that responsibility with considerable vigor.
“There has never been a more fascinating time to be in education, particularly at an independent school,” Speers says. “We cannot continue to do things the way we have.”
Among the challenges Tower Hill faces is a justification to the community at large of a price tag of $21,000-plus for kindergarten. (High schoolers pay about 28,000.) As a result, maintaining enrollment is difficult, and raising funds to provide sufficient financial aid becomes a paramount concern.
Creating a product that’s worth the money is vital for any private school’s 21st-century survival. A veteran of several different independent posts, Speers embraces the institution and the tasks confronting it. She knows that keeping Tower Hill behind a wall will not serve it or its surrounding environs. It is vital that she help make the school part of the Delaware community while also expanding its reach to the world.
“Independent schools can’t see the market as, ‘This is ours, and we want public schools to struggle,’” Speers says. “That’s when trouble starts. We need to be more agile and creative about what our role is. Our founders wanted to be a private school, very definitely—but in a town and city where public schools are strong. We want to up our game.”
There are many ways to do that. Expanding the curriculum is one. Increasing the endowment is another. It’s important to boost faculty salaries and to offer greater options for staff to continue their education and development. Exposing the student body to diversity and global concerns is also crucial. Speers brings a competitive enthusiasm to her role, spending her first year creating initiatives to spark growth and improvement. There’s a lot to do, and it seems like Speers wants to get it all done—quickly.
“The sense of energy and commitment and pride that she has re-instilled into the institution has been phenomenal,” says 
Tower Hill trustee Michelle Shepherd, who chaired the head of school search committee and is a parent of two current students. “She’s a workhorse who wants to do a lot, and she does. The pace of change is dramatic.”
It wasn’t that long ago that Speers decided she wanted to learn how to play the flute. She’d always liked the instrument, and she advanced enough that she was able to play at a recital in front of her husband, Tom, and two children, Nellie and Guthrie. She chose “Twinkle, Twinkle Little Star.” According to Speers, she was applauded for her enthusiasm and dedication.
It wasn’t her sole self-improvement project. A former collegiate tennis player, Speers had always been a baseline specialist, à la Chris Evert. A few years back, she decided to learn how to put topspin on her shots. Over two spring breaks, she enlisted the services of a coach and spent four hours a day hitting forehands. Eventually, she made enough progress to satisfy herself and is now capable of attacking opponents in a variety of ways. “At first, they all went into the net,” Speers says, not masking her frustration.
She’s also attacking her tenure at Tower Hill in multiple ways. The head of an independent institution must be able to handle many different areas of school life. When Speers ticks off her goals for her time there, it takes a while. She wants Tower Hill to develop “exciting partnerships” within Wilmington and to confront some issues vital to the region and beyond, such as poverty and environmental sustainability. Speers expects Tower Hill’s curriculum to reflect her global perspective. The school will offer a Global Scholars Certificate, and Speers hired a director of global initiatives to spearhead programs designed to more fully expose students to the world.
“We’ll be known and sought after nationally for our curricular initiatives,” promises Speers. “And our kids will be engaged in service, learning beyond just the basics. We want it to be part of our curriculum.”
And … “We will raise a little money,” she says.
Speers’ background has prepared her extremely well for this point in her career. She came to Tower Hill after serving as head of the Ethel Walker School in Simsbury, Conn. She’s also been assistant head at Episcopal Academy in suburban Philadelphia and has had stints at Calvert School and the Bryn Mawr School (her alma mater), both in Baltimore, and the Loomis Chaffee School in Connecticut. A Middlebury graduate with a master’s degree from Johns Hopkins University, Speers is steeped in the independent-school culture.
That experience was essential to her candidacy. “We didn’t want someone who hadn’t seen greatness before,” says Shepherd.
More importantly, Tower Hill was looking for someone capable of embracing the school at a tough time in its history. Wheeler’s arrest and conviction had knocked the school back considerably, and Tower Hill was hoping to find someone capable of bringing the community’s eyes back to campus for positive reasons. Speers has worked quickly to integrate herself into the student community by serving as an advisor and refusing to back away from difficult issues. She understands the need to refresh and invigorate the faculty and met with virtually every teacher before the school year started.
But Speers isn’t looking for plaudits. Instead, she’s looking for solutions and pathways to the future. Her vision is one that wraps 100 years of Tower Hill history into a 21st-century approach that is capable of vaulting the school into the forefront of education in Delaware and the nation.
“I very much expect that, if we’re aligning the stars the way we should and can, Tower Hill will be seen as a school of Wilmington and the world in real, exciting ways,” she says.
