Rethinking School Leadership During Challenging Times

Leading a day school has never been more complex. From heightened security concerns and mental health challenges to navigating culture wars, today’s Heads of School are expected to wear many hats — often outside their training as educators. In this interview, Evolve Consultant Benjy Cohen draws on nearly two decades of leadership at Bialik Hebrew Day School to share practical advice, reflect on the biggest challenges facing day school leaders, and guide school leaders on building the systems and support needed to thrive.

Q: What is the biggest challenge facing day school leaders today?

A: The demands of a Head of School are so wide-ranging. Especially since October 7, security is an enormous issue in schools. Unfortunately, culture wars are tearing our wider society apart, and we see echoes of that in our interactions with parents and families. Mental health is also a huge issue for both students and parents. Most of us, including myself, rose through the ranks as teachers and educators; we didn’t become Head of School because we were security or public health or mental health experts, and yet we now need to fulfill those roles as well. 

Q: Tell us about your experience as Principal and Head of School at Bialik Hebrew Day School. What accomplishments are you most proud of? 

A: The school doubled in size during my tenure, including the construction of a second campus. I created a professional development program with small group learning communities and revamped our advancement department. You can’t run a big organization like that by yourself, and I’m most proud of the leadership team I assembled — really great and talented people. 

Q: What advice would you give to day school leaders? 

A: It’s easier to run a big school than a little one, because you’re never alone and never lacking people to bounce ideas off. If you’re working in a small school, I encourage you to find thought partners to collaborate with. Additionally, every Head of School has strengths and weaknesses–whether it be in fundraising, communications, educational vision, or strategic planning. Identify the areas in which you have less expertise and bring in experts to fill in the gaps — whether that’s through more staff, consultants, or training. So much of a school’s success depends on the lay leadership, so I also recommend investing in your board and making sure you have the right people at the table. 

Q: If I’m a day school leader looking to work with you, what kinds of problems could we tackle together? 

A: I really like problem-solving and analyzing things from different directions. As a consultant, I try to listen and ask a lot of questions so I understand something fully before I dive in. I’m eager to help Heads of Schools and board chairs set up strong, supportive systems around them. School leaders need to understand what a high-functioning fundraising team looks like. What should we be expecting from our marketing or admissions department? And how do I work with my board leaders most effectively? Those are often the most difficult set of relationships and the most impactful for a head of school. I’m also excited to help Heads of School navigate strategic planning and build their emotional IQ, which is so important when you have to manage lots of relationships. 

Q: What are you passionate about outside of work? 

A: I enjoy swimming and watching sports, playing chess and bridge, and spending time with my family; my wife and I are proud parents of three and grandparents of two.
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If you are interested in connecting with Benjy, set up a complimentary introductory call here.