In the later years, the work turns inward and outward at once. The focus shifts from momentum to meaning, from building to tending. Leaders are thinking less about what comes next and more about what endures.
This article appeared as "20 Years, 20 Lessons” in the Summer 2026 issue of Independent School.
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.
By the Numbers
Across our INH 2006 cohort of heads:
Just over a third of us are still practicing heads of school. Of this group, more than 80% are in K–12, 6–12, or 9–12 schools. Only five remain in K–6 or K–8 headships, one of whom will be retiring this summer.
About a third of us have retired. Notably, only two did so during the height of the COVID-19 pandemic—just two retirements between 2021 and 2022.
“Retirement” is hard to define; many moved from headship into consulting, recruitment, trusteeship, or other leadership roles.
There have been seven school closures or mergers.
The median headship tenure has been 7.5 years.
Only six remain at the schools where they started.
A few individuals have each completed up to seven headships and interim headships during this 20-year period.
Sadly, we lost two of our group, Lee Ann DeLima and Bruce Pollock.
Amy Vorenberg
LESSON 1: Save your energy. A real emergency may happen tomorrow. Leadership preparation teaches us to manage budgets, enrollment pressures, and long-range planning. But the defining moments of headship often arrive without warning: supporting an anxious faculty member, guiding families through disappointment, or helping students persevere when effort falls short. Schools are human communities, and leading them well requires patience, empathy, and comfort with ambiguity.
LESSON 2: 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.
LESSON 3: 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.
LESSON 4: Healthy boundaries are essential. Many heads are drawn to independent schools because they value connection and community. Over time, however, sustainable leadership depends on clear boundaries. I did not always draw them well, which led to self-inflicted challenges—especially when I had to let go of someone I had worked with closely and considered a friend. I learned the hard way that respect, clarity of role, and appropriate distance enable heads to make difficult decisions fairly and preserve trust across the institution. Boundaries are not barriers to community; they are conditions that allow it to thrive.
LESSON 5: It’s a family affair. The demands of leadership extend beyond the individual in the role. Spouses and partners often shoulder unseen sacrifices—relocation, visibility, and repeated integration into new communities. Their support makes the work possible and reminds us that leadership is never undertaken alone. My 36-year marriage felt its greatest strain as we relocated for my job, I spent countless late nights at school, and my partner was often overlooked by those in positions of power. Tend to your most important person or people: Family comes first.
Mark A. Devey
LESSON 6: Delegate. Over the course of our careers, we learn to wear many hats, and, at times, it might feel easier to handle a situation on our own rather than to trust an administrator. But their job is no longer your job. Your responsibility is to develop the people around you: to coach them, support them, and give them the confidence to lead. When administrators feel trusted, they grow in both skill and judgment, and the institution is stronger for it. Strong leadership is not about doing everything yourself; it is about building a team capable of carrying the work forward.
LESSON 7: Do not lead for popularity. Everyone wants to be liked, and in a close-knit school community, that instinct can be especially strong. But leadership cannot be driven by the desire for approval from administrators, faculty, students, or parents. Instead, vision and values must guide decisions—even when that means making difficult or unpopular choices. Approach those moments with empathy and respect, but do not avoid them. A leader’s responsibility is to serve the school’s long-term interests. In the short term, some will disagree; over time, however, leaders who act with integrity and consistency earn respect.
LESSON 8: 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.
LESSON 9: 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.
LESSON 10: Emphasize mental health. Mental health should be an open and honest part of every school community. I tell students, faculty, and parents that everyone needs a sounding board at times. During particularly challenging periods in my career, I have spoken with a therapist. Leadership carries significant responsibility, and it can help to talk with someone outside one’s immediate circle. By acknowledging this openly, we give others permission to seek support when they need it. Seeking help is not a weakness; it is often essential to living a balanced, healthy life.
Carolyn Chandler
LESSON 11: 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.
LESSON 12: Say “yes.” An unanticipated benefit of being a new head, and in my case, the first female head of school, was discovering how many ideas came my way. A teacher: “Could we start an after-school program? I’ll organize it, and the school will make money.” Yes. A parent: “Could we dismiss early before Thanksgiving to help with travel?” Yes. Students: “Can we get out a day early for Jazz Fest?” No. Over time, I learned to trust that better ideas than mine could—and would—emerge from many sources, especially within my administrative team. It was a pleasure to (mostly) say “yes.”
LESSON 13: 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.
LESSON 14: Connect with students. Those of us who came into leadership through the academic route often miss the closeness we once had with students—and we know our work as heads must be informed and enriched by their perspectives. Attending student events wasn’t enough for me, so we began scheduling lunches with small groups of seniors, inviting them to reflect on their years at our school. Pizza helped ease conversations that were sometimes strained but often quite wonderful—at least for me.
LESSON 15: Celebrate. Even in difficult times, schools offer many reasons—and many ways—to celebrate. When we were finally able to restore our traditional linen service in the dining room, replacing those awful, noisy paper tablecloths, we declared “White Linen Day” and invited everyone to wear white. Almost all the lower school students did. Almost half of the middle school joined in. Almost none of the upper school students did. We laughed and celebrated anyway.
John Huber
LESSON 16: Get to know each trustee. Heads often focus time on a few key relationships, such as the board chair or members of the executive committee. This is understandable, as these individuals help move the board’s work forward. But it can also feel exclusionary—or worse, clubby—to other trustees. Heads should schedule annual, agenda-free, one-on-one conversations with each trustee to build trust, understanding, and shared purpose.
LESSON 17: Hold on to great board chairs. There is no greater marker of institutional stability than a long, successful partnership between a head and a board chair. Few things are more challenging than learning to work with a new chair—especially when turnover is frequent. I’ve experienced both ends of that spectrum: the steadiness of long-serving chairs and the strain of rotating through five board chairs in six years. When continuity serves the school well, bylaws can—and should—be revisited to allow effective board chairs to continue their work.
LESSON 18: Don’t sweat the snow days. No decision invites more critique than whether to close or delay school for snow.
Early in my career, I realized that my classics degree did not double as a meteorology degree. So, I instituted a policy of basing our decision on the status of the local public school district, whose teams have the resources to assess road safety. While I could hop in my 2018 VW GTI to test conditions myself, I’m far more comfortable relying on the expertise of district facilities and transportation teams to guide the call.
LESSON 19: 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.
LESSON 20: 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.
Learn Together
Programs like NAIS’s Institute for New Heads and the Fellowship for Aspiring Heads offer school leaders the space to learn, reflect, and connect with others on the headship journey. Similarly, NAIS’s Leadership Through Partnership program, for heads and their board chairs, creates dedicated time and space to continue the conversation and strengthen their relationship. Register for this year’s event, which will be held October 22–23 in Washington, DC, and learn more about NAIS Leadership Academy.