Beth Sugerman, Norwalk head of school, Winston Preparatory School

Local heads of school in Westchester, Fairfield and Dutchess counties talk about lessons learned from the pandemic, inspiration, superpowers, what makes them smile and – in one case – the benefits of dogs on campus.

Winston Preparatory School is an innovative private day school for students through 12th grade with a variety of learning differences, including dyslexia and executive functioning difficulties such as attention deficit hyperactivity disorder. Winston has seven campuses, including the newly designed one in Norwalk.

After completing an undergraduate degree in speech and language pathology, Sugerman earned a Master of Science degree at Teachers College, Columbia University and was sent to Winston Preparatory School in Manhattan for her placement experience. Twenty-four years later, Sugerman is the head of the school’s Norwalk campus, a position she has held for 14 years. 

What is something surprising about your school that others may not know about?

“How happy kids are to be here. How welcoming a community Winston is. I think that one of the highest compliments we’ve received is how quickly students who perhaps felt unsuccessful and did not like school before, get up and come to school. We also hear that from new faculty members as well — how welcoming the teachers are and supportive and helpful. And there’s a true sense of community versus ‘this is a school for kids with learning challenges.’ This is a school where kids learn in a manner in which they can become successful. When kids feel safe and understood, anything’s possible.”

Which aspects of running a school are most appealing to you? 

“I love the collaboration. I love working with smart professionals and people who understand what we do. It’s a bit outside the box — grouping students with similar learning profiles, teaching to that profile, providing the one-to-one program, targeting students’ greatest areas of needs academically and, sometimes, socially-emotionally. I think that we see our kids as puzzles and we like to work together and figure out that puzzle so we can provide the best and the most optimal experience. Ultimately, we want the kids to feel successful and feel good about themselves and feel that they are capable. And a lot of our kids come to us without those abilities or feelings.”

What is your superpower? 

“I think my superpower is supporting students, families and faculty — kind of maintaining positivity, problem solving and thinking ahead.”

Did you have another career before going into education?

“Actually, I did. I had a few careers. My initial career was family driven. I come from a background of folks in the fashion industry in Manhattan and I went to college for a few years and felt that wasn’t the direction I wanted or was succeeding within, so I worked in the fashion industry and loved it. After (subsequently) working as an executive assistant for an extremely philanthropic chairman of a very successful company, I decided, with my husband’s encouragement, that I wanted to finish my degree in speech-pathology.” 

What inspired you to choose a career in education?

“When I was researching the career, I liked the science piece. I think that what I love about Winston is that we look at the science of learning and the art of teaching. And I think it’s a combination that’s provided the successful mission here. We don’t consider ourselves just educators.”

What reaffirms your career choice?

“I think graduation day is the most rewarding day for us all. Our seniors are provided the option to give a personal speech. And this past year we had 17 out of 24 seniors speak to their experience — who they were when they arrived at Winston and who they are leaving. That’s when I tell them, “This was a day we live for,” and it kind of keeps me going for a while.”

What do you do to recharge in your free time?

“I have three dogs and they like to take nice long walks, and they get me out every day, no matter the weather.” 

Do your dogs come to school with you? 

“They do. I like to say there are more pictures of them in the yearbook than me. They are all rescues. They’re kind of like honorary therapy dogs and kids love to come in and visit with them or, if they’re struggling, they like to hang out with the pets and, of course, feel better soon after.’

Winston Preparatory School at a glance

  • Head of school: Beth Sugerman
  • Number of faculty and staff: 54
  • Student enrollment: 125
  • Annual tuition: $73,300 

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