Vocation: Education

The Gowan Group Finds the Right Schools for Students

As a parent with many options, getting your child into the best possible school money can buy is your top priority, right?


“You want a community that accepts and values your child,” says Chris Pryor, president and founder of The Gowan Group, a Westport-based independent school consulting firm celebrating its 10th anniversary in Westport. “Everyone wants strong academics, of course, but it’s about finding a place where your child is comfortable and can stretch themselves. 

“It’s really about connections.”

And that’s where Chris and his team come in. With a decade in the business of helping schools navigate the highly competitive world of strategic planning, marketing and branding, his team is uniquely adept at finding the perfect fit for children and teens.

To say Chris knows a thing or two about independent schools is a true understatement. Chris Pryor lives and breathes independent schools.

He has held leadership positions at New York’s Harbor Country Day, Hackley, Rye Country Day and Tuxedo Park schools and The Independence School in Delaware, and was actively involved in the New York State Association of Independent Schools.

With a bachelor’s degree in elementary education from Roanoke College and a dual master’s in educational administration and curriculum and teaching from Teachers College, Columbia University, he started his career journey as a student himself at Kent School.

There, Chris met Don Gowan, a fellow Kent alum who was his boys’ lacrosse coach and dean. It was Gowan who would show Chris just how life-changing a good mentor can be.

“Don Gowan stood for integrity, honor, fair play, respect and innovation. Gowan Group emulates him in these ways,” Chris states of the firm’s namesake.

With more than 30 years experience in the independent school system, Chris has consulted with, learned from and befriended a diverse group of trustees, alumni, admissions and development personnel and more. He’s also assembled The Gowan Group’s savvy team, capitalizing on their insider’s view on independent schools in Connecticut and beyond.

“We all went to private school and we all worked in them for years,” Chris remarks. “One of us had a father who was the headmaster at Deerfield. He grew up there. We have a tremendous amount of experience and know the schools well.”

Leading the placement team is Director Paul Baly, whose 25-year career includes working in a variety of boarding, K-8 and K-12 schools.

“I saw over and again the transformational nature of an independent school education. That transformation relies on deep and meaningful relationships between students, teachers and parents,” Paul says. “When kids feel seen and known, they have self-assurance to become the very best versions of themselves. Achievement and success become the outcome.”

While the state of independent day and boarding schools in New England is strong, what they’re looking for in a student has changed dramatically since Chris was at Kent.

“Gone are the days of only the elite going to independent schools,” the Westport father of three says. “Schools have become far more inclusive. They value a diverse student body. And the boarding schools have an international student component.”

As a result, many offer millions in financial aid and actively solicit applications from school systems across the state. With so much opportunity and so many schools touting what they consider their distinctive qualities, the search for the best school for each child can be daunting.

“They’re all very different and each has its own character,” Chris says. “Hotchkiss is very different than a Pomfret or a Canterbury. And some schools are real pressure cookers. Some kids thrive in that atmosphere – and some do not.”

The Gowan Group takes time to get to know each family it serves, learning as much as it can about a child’s strengths and challenges and unique way of learning and going about the day.

Pro tip for finding the perfect fit? Start this fall for September 2024 admission. With application deadlines in the late fall and early winter, families should give themselves plenty of time to research and visit the schools on their wish lists, Chris says.

The Gowan Group can assist along the way, helping first-timers navigate the complex world of K-12 placements and coaching prospective high schoolers on interview technique and gathering their ideas and anecdotes to shine in personal essays. Even students who don’t need that much individualized attention might benefit from a strong sounding board or sage advice for looking for schools that cater to specific learning needs.

“We know the terrain and the best way is a thoughtful, personal approach,” Chris says. “The Gowan Group has never done anything cookie cutter.”


“I saw over and again the transformational nature of an independent school education. That transformation relies on deep and meaningful relationships between students, teachers and parents,” Paul says.

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