Leslie Zuckerwise Looks Ahead to Next Chapter After Rising from Assistant Teacher to First Manhattan Division Head

Mrs. Zuckerwise is pictured on the 2018 First Day of School.

Throughout her life, Leslie Zuckerwise has been fearless in taking leaps of faith into unknown waters and her 20 years at Windward have been no different. Following successful careers as a paralegal, computer operations manager, and resource room teacher, Mrs. Zuckerwise considered what her next move might be after her twin daughters, Lisa and Gail, went off to college. She realized that in all her previous positions she had assumed a coaching, mentoring, or teaching role, and she loved the impact she had working with children.  

“I was talking about this with my long-time friend Shelley Donato. Two days later, she called me and said she set up an interview for me at The Windward School, where she worked, and Shelley said, ‘Don’t embarrass me!’” recalled Mrs. Zuckerwise. 

In 2001, Mrs. Zuckerwise began her first day at Windward as a Westchester Middle School assistant teacher. Compared to others in her cohort, she had considerably more life and work experience, yet Mrs. Zuckerwise was an enthusiastic student and was never afraid to ask questions. She signed up for every single course offered through the Windward Teacher Training Program (WTTP) to familiarize herself with Windward’s methodologies.  

“I gained a lot of clarity and knowledge from Windward about the best way to teach, and I could see the results in the classroom,” said Mrs. Zuckerwise. “I was in the classroom for many years, teaching fifth, sixth, and eighth grades in language arts, math, and social studies, and it was amazing to see the small victories daily.”  

Over the years, Mrs. Zuckerwise perfected her craft as a lead teacher, and she was awarded the Isabel Greenbaum Stone Master Teacher Award in 2010. She also forged ahead as a pioneer, being the first to introduce a SMART board in her classroom, the first to provide instructional technology support, and the first to start a new teacher staff development program with Marsha Finkelstein.  

Her talents as a superb educator, caring mentor, and forward-thinking leader made it clear that Mrs. Zuckerwise could have an even greater impact as an administrator. In 2011, she moved to Westchester Lower School to serve as assistant division head before being named division head in 2012.  

Around this time, Windward began planning to expand the School’s capacity to serve more students, and a key feature of this bold vision was to build a new campus in Manhattan. Windward sought a trailblazer who would both be able to lead two divisions and establish a community that would continue the excellence of Windward’s program. The best person to become the first Manhattan Lower & Middle Schools Division Head? Mrs. Zuckerwise.  

Undaunted when construction of the Manhattan campus was not completed for the start of the 2015-16 school year, Mrs. Zuckerwise, the rest of the Manhattan team, and head of school Dr. Russell exercised their flexibility and grit to prepare a temporary Upper West Side location to welcome Windward's first Manhattan students.  

“When those children showed up on that first day, it was pure joy,” said Mrs. Zuckerwise. “Half the battle was getting the external components ready, but now we had to go deliver and teach those kids “the Windward Way.” I took great comfort in knowing I had brought with me a very well-trained and talented group of teachers from Westchester. We were not going to fail—that wasn’t an option for anybody—and we were taking this plunge together. We knew this wouldn’t be without challenges, but we built a home with each other through a warm community effort.” 

"We were not going to fail—that wasn’t an option for anybody—and we were taking this plunge together. We knew this wouldn’t be without challenges, but we built a home with each other through a warm community effort.”

The following year, Mrs. Zuckerwise settled the Manhattan community into their permanent home on the Upper East Side, and the last five years have been a happy whirlwind. On any given day, Mrs. Zuckerwise embraced the enormity of her responsibilities and shifted seamlessly between attending to the needs of “the littles” and “the young adults.” She treasured every part of being the leader of the Manhattan campus, from showing her school spirit on Field Day and at sporting events, to conducting read alouds with the second graders, to greeting new families on their first official visits to campus, to feeling immense pride in the students who were moving up and graduating.  

When asked how she navigated through the ever-increasing demands of her career, Mrs. Zuckerwise was quick to respond. 

“There is no way I would have been able to do this without my husband, Peter, and two girls. I was very happy in the classroom, but we always talked through each move. They would say, ‘Do it!’ My family has been ridiculously supportive.” 

Mrs. Zuckerwise also was complimentary of many of her Windward colleagues. 

“I have been very lucky with my mentors between Jay Russell, Sandy Schwarz, Sheila Okin, and Betsy Duffy. They have been big influences in my career. I tell all my faculty that it is a sign of strength when you know that you don’t know something, and I am fortunate I could always turn to those mentors for their perspective. Chris Eberhard, Alexis Pochna, and I have worked together for years now, and we really take the time to hear one another so we can deliver on the mission of the School. I know I have Jon Rosenshine’s ear for anything I need. I am fortunate to have Jeremy Bletterman and Lori Squillante as assistant division heads to lean on.” Mrs. Zuckerwise is eager to keep in touch with her Windward colleagues and hear about the School’s future successes.  

On the announcement of her retirement, Head of School Jamie Williamson congratulated Mrs. Zuckerwise, stating, “On behalf of the entire Windward community, I would like to extend our heartfelt thanks to Mrs. Zuckerwise for her dedicated leadership and extraordinary accomplishments that Windward students, faculty, and staff members have achieved under her direction.” 

Former Head of School Dr. John J. Russell shared, “As division head, Leslie faced many challenges with dignity and grace. Guided by an impeccable moral compass, she provided the strong leadership that is essential in challenging times.” 

Director of the Windward Teacher Training Program Sandy Schwarz said of Mrs. Zuckerwise, “Her incredible dedication to being ‘the best of us’ has been apparent in the continuous challenges she has welcomed and met with determination to always put our students first, no matter the time and energy that was required of her.” 

Westchester Lower School Division Head Alexis Pochna noted, “Leslie is a true risk taker, and to say that she thrives on new challenges is an understatement. She has been an important mentor and role model for so many, and pondering what she would do in a situation will forever be a guiding star for me." 

In her next chapter, Mrs. Zuckerwise will be recouping a lost year of family time and moving to Nashville, TN, to be closer to her daughter, son-in-law, and grandchildren. She plans to take some personal time but is certain that, professionally, she will find a way back to working with students again.  

“This has been one of the best experiences I ever had,” said Mrs. Zuckerwise. “I am so fortunate to have been able to wake up and say every day that I am really excited to go to work today. I am a better person for being a part of The Windward School.”