This blog post is a preview of the Summer 2026 issue of Independent School magazine; it is an excerpt from from the article “20 Years, 20 Lessons.”
In July 2006, 64 new and nearly new heads of school gathered in Washington, DC, stepping into the NAIS Institute for New Heads (INH) with excitement and a quiet sense of awe. We came eager to learn what this work would demand of us and how, exactly, one leads a school well. The formal sessions mattered. But what stayed with us, and ultimately shaped our careers, happened in the smaller rooms, in conversations that were candid, vulnerable, and human.
The four of us were assigned to a homeroom led by Reveta Bowers, the longtime head of The Center for Early Education (CA). With empathy, humor, and unmistakable clarity, Bowers drew us together and taught us to lean on one another in those early, fragile days of headship. She modeled something just as important as strategy or best practice: the power of connection and the reassurance that, in the end, things would be ok.
Twenty years later, our paths have diverged, but the wisdom endures. Drawing on our collective experience, we share the lessons that continue to shape effective headship—hoping to inspire the next generation of heads as we once were.
The head sets the tone.
In moments of uncertainty, the school community looks to the head not just for answers but for perspective. Whether a school is navigating a death in the community, a major change initiative, or an unplanned transition, emotions can move quickly through an institution. A leader’s calm presence can prevent difficult moments from becoming crises. Maintaining composure—especially when situations feel urgent or personal—allows for thoughtful decision-making and reassures the community that challenges can be met with care.
Link arms with your board chair and walk together.
No relationship has a greater influence on a head’s success. Trust between head and board chair must be intentionally cultivated through transparency, communication, and mutual respect. When alignment exists, governance becomes constructive and forward-looking. When it does not, a head’s tenure is often short. I missed early warning signs—delayed meetings, executive sessions, and an awkward silence where collegiality once lived. When one of my headships ended abruptly, it was painful and professionally humbling. Heads should remember: We are all interims. No headship lasts forever. With integrity intact, onward.
––Amy Vorenberg, most recently head of school at Nantucket New School (MA)
Be purposefully present.
Early in my first headship, I tried to be everywhere at once—moving quickly from classrooms to hallways to athletic fields in the name of visibility. One day, an eighth grader—wise beyond his years—offered advice I never forgot: While presence matters, brief appearances can feel more political than genuine. I learned to be visible but purposefully present. Choose moments where you can stay long enough to engage meaningfully—watch a rehearsal, observe a class, or sit with students at lunch. When people experience your presence as sincere, they understand that you truly care about the community and its learning.
No one is perfect.
We strive to create schools where students act with integrity, pursue excellence, and persevere through challenges. Those goals endure. But today’s students face pressures previous generations did not—widespread anxiety, constant comparison amplified by social media, and lingering disruption. Students will make mistakes. When they do, our response must balance accountability with empathy. Understanding does not mean lowering expectations; it means recognizing that growth often requires patience, guidance, and sometimes a second chance. Leaders who model this balance create a culture in which students and faculty alike feel supported as they do their best work.
––Mark Devey, head of school, Perkiomen School (PA)
It’s not about you.
During a sleepless night after a hurricane devastated our city and ravaged my school, terrible thoughts filled my mind: What if my photo is the last photo on the headmasters’ wall? What if I can’t make the finances work? What will people think of me if I fail? Then, unexpectedly, a quieter thought arrived, almost as a gift: It’s not about you. It’s about the work. Do the work. I laughed and went back to sleep and got up knowing there was plenty to do. I didn’t know how to solve everything, but I knew how to begin. Setting my ego aside released new energy.
Make friends.
Almost every head of school has much to learn about this dazzlingly complex, demanding, ever-changing job. Fortunately, there are many opportunities to do so through involvement with NAIS, regional accrediting associations, The Heads’ Network, and the Klingenstein Center at Columbia University. Through these experiences, I met—and became friends with—school leaders from across the country. It has been, and continues to be, a privilege to learn from and through these cherished friendships.
––Carolyn Chandler, partner, Strategic School Leadership
Embrace support in your own time of need.
In late 2021, I was diagnosed with lymphoma while serving as an interim head, three time zones away from my family and very much on my own. I had hoped to keep my medical condition private, but as chemotherapy progressed and I lost my hair, that became impossible. So, I shared the news with my still-new school community, uncertain how it would be received. Though we had been working together for only half a school year, the generosity they extended helped carry me through a deeply uncertain time.
Be present, be proximate.
One of my former schools was discarding its heavy wooden student desks, and I rescued one as a souvenir. I now put it to use by placing it in the hallways and working there each day I can, in the presence of students and teachers. Partially inspired by Frank Boyden, former headmaster of Deerfield Academy (MA)—who kept his desk in the school’s main entrance, amid the heaviest traffic—I enjoy being close to the action without interrupting the flow of learning. Nothing brings me greater joy than spending a day in the hallways, greeting students, and listening to the sounds of school.
––John Huber, head of school, Sycamore School (IN)