Experts shared knowledge on AI, navigating political tensions, affordability
Amid a continued surge in enrollment for Jewish day schools across the U.S. and Canada, four Houston Jewish day school heads of schools joined 100 heads of other schools for Prizmah’s biennial retreat in Houston on Feb. 1-3.
Leaders in the field, along with keynote presenters, led sessions covering topics such as navigating leadership challenges and opportunities with nuance and intention, developing ethical and future-ready artificial intelligence strategies for schools, addressing affordability and more.
Representing Houston, Jennifer LeVine (Jack Segal Academy), Rabbi Jordan Silvestri (Robert M. Beren Academy), Dr. Michelle Barton (The Shlenker School) and Rabbi Enan Francis (Torah Day School of Houston) took part in the learning session.
“One of the highlights of the year is always being able to connect with other Jewish day school heads from around the country and truly learn with one another,” LeVine said.
“There is something incredibly powerful about being in a room with colleagues who understand the unique joys and challenges of this work. Hearing firsthand experiences and intentional practices each day made the learning feel both practical and deeply meaningful. I left the retreat feeling energized, supported and more grounded in the impact of our shared leadership.”
Rabbi Silvestri agreed: “Sharing a space where we were able to be vulnerable, courageous and open with dear friends and colleagues that deeply understand the field allowed us to fully embrace the learning over the three days as we explored our head of school story, our strengths and ways we can continue to improve ourselves and our schools.
“It was, as always, one of the highlights of my year and a privilege for me to be part of such an inspiring field.”
Sheila Dubin, a Fortune 1000 leadership coach from Cultivating Leadership, served as facilitator in residence, leading sessions on frameworks for effective decision-making in complex times and navigating real-life tensions to sustain healthy school communities.
Christina Lewellen, president and CEO of the Association of Technology Leaders in Independent Schools, spoke about AI in schools and other technological tools and strategies heads of schools can use to maximize human contributions.
“Jewish day schools are essential to the strength of our community into the future,” said Paul Bernstein, CEO of Prizmah. “Heads of school are at the forefront of ensuring we have excellent, growing and increasingly affordable schools. In a complex world with many challenges, they carry the burden of ensuring the success of each school, creating the best environments for their students, faculty and the entire school community.
“The Prizmah Head of School Retreat offers the tools, knowledge and connections to lead with confidence and care, learning with and supporting their fellow heads.”
Reflections on the Prizmah Retreat
By DR. MICHELLE BARTON
One of the hardest truths of school leadership is that many of the challenges we face are not solvable in the traditional sense. They can’t be fixed with a checklist, delegated away or resolved by finding the “right” answer.
Sitting with that reality was one of the most meaningful gifts of spending time recently with fellow heads of school here in Houston.
That shared recognition created space for a deeper and more honest conversation about the nature of our work. What felt newly clarified was the distinction between problems that can be solved and tensions or polarities that must be managed over time.
In our work, it is tempting to treat every challenge as technical, something to diagnose, decide and move on from. But many of the questions that matter most – around affordability, belonging, innovation, governance, growth and trust – require leaders to hold multiple truths at once. They demand nuance more than certainty and stamina more than speed.
Naming that distinction changed how I understood my own leadership questions. That framing shifted something important for me. Instead of asking, “How do we fix this?” I found myself asking, “How do we live inside this tension with integrity?”
Against that backdrop, one of the most impactful aspects of our time together was the intentions and stories shared by colleagues about turning points in their leadership.
What struck me was how rarely those shifts came from public success. More often, they emerged from moments of uncertainty, missteps or sustained tension, the slow work of learning when to push, when to pause and when to let go. Hearing those stories reframed a challenge I’ve been carrying myself, how to honor deep roots while still making room for new growth.
As those reflections accumulated, the work began to turn inward. As the retreat ended, the focus shifted in a way that felt both grounding and necessary. I was reminded that who we are as leaders – our identities, instincts, default responses and our origin stories – shape every decision we make, especially in complex environments.
Self-awareness is not a soft skill or a private exercise; it is a strategic resource. When leaders understand how they show up under pressure, they are better able to lead with clarity, flexibility and discernment.
This inward reflection was reinforced by the collective nature of the experience itself. Perhaps most importantly, I was reminded that leadership is not meant to be practiced alone.
Time and again, moments of insight came not from instruction, but from conversation, from sitting with peers who understood the weight of the role and were willing to wrestle with hard questions out loud. Challenges I had been carrying quietly felt lighter when examined collectively. Possibilities I hadn’t yet seen came into focus through shared reflection.
I did not leave with a playbook or a set of best practices. I left with something far more sustaining: a renewed confidence that leadership is a collective endeavor. Our schools are stronger when we think together, challenge one another and give one another permission to name the complexity of our work as heads of school.
Dr. Michelle Barton has served as head of school at The Shlenker School since 2018.