Looking at Lengthy Head of School Tenure

Summer 2022

By Danny O’Brien

NAIS-3-FINAL_1.pngThis article appeared as "The Long View” in the Summer 2022 issue of Independent School.
Reveta Bowers joined The Center for Early Education (CA) as head of school in 1976. Full of energy and talent, Bowers envisioned the Center as the thriving national model of innovative programs for students in nursery and elementary school. Unfortunately, the daily demands of enrollment, hiring and evaluation, and student issues more than occupied her time. Frustrated and burned out, she resigned after four years at the institution. The Center remained a small niche neighborhood school.
In 1990, a coast away, Drew Casertano left Loomis Chaffee School (CT) to become head of Millbrook School, a struggling boarding school in upstate New York. He saw what Millbrook could be, imagined significantly larger enrollment and a rebuilt campus. But the trustees failed to support him, and faculty and families who had the ears of different board members eventually wore him down. Perceiving all problems and no joy, he left the school just two years after launching an ambitious strategic plan, forcing Millbrook to start the visioning process all over again with a new head.
Obviously—thankfully­—these stories aren’t true. Bowers is retiring in July 2022 from The Center for Early Education after a storied 42-year tenure as head of school. Casertano left Millbrook in 2021 after 31 transformative years at the helm. Both heads achieved their ambitious visions, and both schools are thriving.
But imagine if these scenarios were true. For many heads and schools, these stories and outcomes are all too real. More head tenures nowadays end in truncated and disappointing ways. According to consultant John Littleford, the average head hired in 2021 will last less than six years on the job—a trend that serves neither heads nor the institutions they lead. A school with regular leadership turnover might survive, but it won’t thrive. In addition to limiting institutional potential, short head tenures negatively impact heads of school themselves. The threat of regular turnover reduces the appeal of the role. Frequent work-related moves—which often accompany professional transitions—are disruptive not only for heads but for their families. Rebuilding networks with each new relocation makes it harder for these communities to be the support a head needs.
Some turnover makes sense. The head of school position is a hard and lonely one. The work requires constant humility. Heads regularly subvert their own personal desires for what their schools need from them. It’s exhausting. “I fear we are going to have more disrupted and unnecessary departures,” Bowers says. “There is too much pressure and not enough joy. Folks would rather do anything than run a school.”
Yet Bowers, Casertano, and a score of other school leaders have demonstrated the value of long headships. And the benefits—to schools and heads—are too great to simply accept that extended tenures will need to be rare. Multidecade headships do not happen by accident, however; they require intention, foresight, and nourishment to achieve. The good news is that many leaders and school communities have successfully made them happen, and there are widely applicable lessons that can keep them going.

Generational Work

After receiving yet another email about a disrupted head tenure last spring, I went on a quest for insights about why some school leaders far outlast many others. It led me to have conversations with heads who led their schools for 20 years or more. Perhaps the most immediate insight is that these schools reached their prosperity over a period of decades, not years. At all schools, creating, articulating, and implementing a vision; establishing a cohesive and effective faculty; and rallying a community to support that vision is generational work.
Before Casertano could fully implement the vision he developed for Millbrook, 20 years went by. “It took my first two years to get a strategic plan done,” he says. “Then we had to raise $40 million dollars to fund the goals of the plan, which was 10 times more than Millbrook had ever raised previously. We were enrolling 170 students; I saw a thriving Millbrook with about 300. But in this first plan, I could get the board to agree to a target of 250. It took a whole new plan to get to 325. Two decades passed before the original vision was fulfilled.”
Keith Shahan says some of his most important work in his 24 years as head of John Burroughs School (MO) was hiring and retaining faculty members and administrators who thrived within the school’s mission—and moving out folks who did not. “This took a long time,” Shahan says. “It was my priority, and I do not know if we would have gotten there had a new head replaced me early in my tenure and come in with a different set of goals.”
Playing the long game is critical. “Over time, I developed institutional memory,” says Rick Melvoin, who was head of Belmont Hill School (MA) for 25 years. “Getting to know the players takes a period of years. Serving as long as I did allowed me to think less about year to year and more about decade to decade—about what Belmont Hill needed to endure.”
Long-term service also creates valuable capital and the sense of trust between the head and various school constituencies that’s required to get things done. Arlyce Seibert, who led the Cranbrook Schools (MI) as head for 23 years, says, “Deep understanding of the school culture and great relationships equal trust. This is especially important in a time of crisis, when you need to spend capital. If you need to pivot, you know who to go to without thinking.” The level to which communities accept evolution in schools rarely correlates with the validity of the change but the trust people have in the person leading it. Several long-term heads have had more success in recent years helping their schools make progress through contentious societal and political issues than have new leaders. “It’s simple,” an organizational consultant once told me. “If you have a relationship with a person, you are more likely to trust their decisions than when you don’t.”

Managing Incredible Demands

The head of school role is immersive and all-consuming, demanding incredibly long hours and even greater emotional energy. This will always be a dilemma to manage, not a problem to solve. It will be hard; boards and heads that do not say this out loud to each other are missing an opportunity. At the same time, the seeming impossibility shouldn’t paralyze school leaders.
Or keep them from recognizing that it’s also possible to derive energy from the job. “If you love your job, if you believe in the mission, if you are doing good work, it only becomes more and more gratifying,” says Suellen Newman who founded The Hudson School (NJ) in 1978 and led it for 38 years. “You become more emotionally invested as you see generations of alumni come through the school.”
None of these long-serving heads avoided the consuming nature of the job. Yet, like Newman, their love for their institutions and belief in the core mission and values motivated them to manage competing personal and professional demands year after year and helped them avoid another common trap: thinking a head can change a school. Leaders seeking to establish themselves for the long run in one place must distinguish between changing a school and making it the best version of itself. Incoming heads need to understand, for example, that their arts school may never offer the most AP classes; the same person taking the helm of a progressive, student-centered school has to accept inherent messiness and experiments that go awry. Bowers did this. She grew The Center for Early Education from 165 to 540 students during her tenure. But she remembers that the Center’s board always wanted a place where kids would feel comfortable, which meant stability and community, goals she kept paramount. Bowers improved the Center while maintaining what it had always stood for.

Getting Out of the Weeds

Every long-serving head I talked with says they led their schools differently in their 20th year than they did in their early ones. This pivoting did not happen organically, though. It took intention and space to reflect. “I think I was successful because I thought of my tenure as several seven- or eight-year headships,” says Steve Piltch, who was head of the Shipley School (PA) for 27 years and is now director of the School Leadership program at the University of Pennsylvania. “After seven or eight years, I needed to reflect again on what Shipley needed from me, how I needed to change my leadership style, or augment my knowledge base to meet a new moment in Shipley’s history,” he recalls. Continuity in leadership helps schools evolve, instead of just getting by, he says. “And you always want to evolve.”
Finding time for this means focusing on the work only school leaders can do. No one else in a school has the same responsibility to achieve results, build teams, remain on the front lines of educational thought, communicate a vision for the school, and maintain good governance. At the same time, few roles need to prioritize in the same way time for self-reflection and seeking feedback. These tasks need to take precedence, and this means that school leaders in the work for the long term need to delegate operational problems and the work others at school are capable of—and perhaps even better at—doing. Other school leaders and administrators can—and should—support them in managing employees, sustaining enrollment, maintaining facilities, supporting students, and communicating with families. While heads will dip their toes more deeply into different aspects of school life over time, this kind of macromanagement allows them to pour their energy into facets of school leadership that will make the biggest difference for their schools and the sustainability of the role.
For example, Melvoin says, “Every few years, new faculty members and administrators want to ‘solve the schedule;’ they think they can eliminate the downsides without creating new ones. And it is important to let them try. Part of your job is to develop new leaders.” But, he adds, “I didn’t need to be involved every time. The first time we did a schedule revamp, I was in the weeds. The next time, I cared about the product, but others led the effort and they kept me updated at important inflection points.”
Macromanagement can also keep the work from feeling too repetitive. Delegating responsibilities—especially repetitive ones, which will always feel new to someone—also offers heads room to continue to learn, reflect, and adapt. “Being too deeply immersed in operations is a recipe for burnout,” says Mo Copeland, who has been a head for 25 years, currently at Oregon Episcopal School (OR), and before that at St. George’s School (WA). This is especially true in small schools, where heads might feel financial pressures that make it impossible for them to delegate operational responsibilities to others. But “even when a budget is tight,” Copeland says, “a school needs to prioritize freeing the head of school to work strategically. It will lead to a good return in the long run.”

Secrets to Success

If evolution and adaptation are critical to a long and successful tenure, what does it look like? How did these leaders evolve and adapt while staying fresh and continuing to provide new energy to their institutions?
They sought feedback. Schools careening from crisis to crisis—with the head of school involved in every one—do not have time to seek feedback, debrief, and ask crucial questions. When heads do not create time for or seek feedback about what the school needs of them and their performance, they’ll be the last to know when something is going wrong—and it will likely be too late to correct.
School leaders often avoid these discussions for fear of being criticized. “People are afraid to have these conversations,” Casertano says, “but you need to have them if you want to be on top of your game—and to know if others think you are.” Shahan brought in outside consultants to conduct 360 assessments at John Burroughs, and Seibert sent annual surveys to Cranbrook constituents to solicit this kind of feedback. “Avoiding defensiveness was the hardest part,” Casertano remembers. “I tried to listen and, when my neck stiffened, I reminded myself to just hear the other person—they were probably right,” he recalled. Successful heads know they have created space for feedback when people are willing to give it.
They built strong administrative teams. These teams were able to address issues independently and understood why providing feedback was essential to support the head—teams that ask hard questions during decision-making processes and present a unified front once those choices are made. Having an admin team with these qualities can make heads feel less lonely and provides protections as a community processes unpopular decisions. “I needed the admin team to push back on me,” Melvoin says. “At the same time, especially during divisive moments, I sometimes needed them to support a decision even if they would have gone in a different direction personally. They would not have done this if we were not a team.”
Building this kind of team takes time. The leaders with whom I spoke cultivated interpersonal relationships with senior administrators, got to know them personally, learned about their career goals, heard their perspectives, and encouraged them to share those ideas with others. People allow others to have human reactions when they see their humanity. This is why building personal, as well as professional, relationships with admin team members was so essential to the long-term success of many heads with whom I spoke.
They cultivated a strong board relationship. Boards, of course, play an outsize role in a head’s success. A high-functioning, collaborative board requires work, experience, and institutional memory. And while establishing a strong relationship demands a high percentage of a head’s time, it is as time-consuming as it is important. As boards go, so do heads of school. “Successful heads understand how important the board will be in their lives,” Casertano says. And the most important relationships to build are with the board chair and chair of the governance committee. These roles—which help manage all trustees—might be the two most important on a board in terms of helping a school thrive and a head prosper for a long time.
Strong board relationships can help with continuity, but when the makeup of the board changes every few years, it can still be quite challenging. Term limits help schools part ways with influential but occasionally ineffectual board members. But, Casertano believes, “Some people use term limits to avoid having hard conversations.” And like him, some observers are beginning to question whether the trend toward board term limits and shorter chair terms are contributing to declining headship tenures. “The problem term limits solves has created unintended—and perhaps greater—problems,” Melvoin says. “What you lose,” Piltch says, “is committed trustees who love the school, understand their roles, have the trust of the community, and work in partnership with the head.” He wonders whether head tenures will increase if board chairs serve longer terms in the role. 
They benefited from external responsibilities. Delegating well allows heads to expand their world and the scope of their work—by serving on the boards of other schools and associations and participating in conferences, for example—which ultimately benefits heads and their schools. It might sound counterintuitive to add more to the plate of an already full job, but says Seibert, “I started joining boards, getting involved with associations and so forth, and that is how I got new ideas and developed new relationships. That’s how I kept making a difference.”
They had a life outside of work. Finding time for hobbies and support networks beyond the school is critical. “I still play soccer in an over-62 league,” Melvoin says. “Those two to three hours each Sunday are invaluable, not only because I love the game, but because I am having fun with a group of people who have nothing to do with my life as a head of school.”
And even though heads need people outside their school and family, it is key to have family support. Newman says her children and husband always knew how important the school was to her. “I was a better partner and a better mother because I was doing something that meant so much to me,” she says. “It was time-consuming, and I have no doubt it was hard for my family at moments. But I like to think that I demonstrated intangibles to my children, such as having a dream and carrying it out.”

Visible Substance and Invisible Essence

The days when Frank Boyden could lead Deerfield Academy for 66 years are long past. Schools are more complex organisms than they were a century ago, and the job of head of school is much more complex. Busy sitting heads of school may read this and shake their heads. Given the demands of a school today, it may seem impossible to prioritize continuing education and generative thinking, feedback and reflection, building strong administrative and board teams, and developing personal relationships outside of school. But the fact is that is the work only a head of school can do.
Short tenures are less transformational for schools, and heads of school leave their mark over generations. In his 1967 profile of Frank Boyden for The New Yorker, author John McPhee described the headmaster as responsible for “both the visible substance and the invisible essence” of Deerfield. In their own ways, each of the heads with whom I spoke made similarly profound impacts on their schools.
And it can be done with joy. “It has been a wonderful life,” Casertano told the Millbrook community on one of his last days. “Our hearts will be full of love for this place, with pride in what we have accomplished, with the sense that we have left it better than we found it.”
Danny O’Brien

Danny O’Brien was most recently head of school at High Mountain Institute in Leadville, Colorado. In July, he will begin his tenure as head of The Putney School in Putney, Vermont.