Surviving, Thriving, and Sometimes Just Enduring; as a Head of School

Winter 2005

By Michael Thompson and Rick Melvoin

EDITOR'S NOTE: Rick Melvoin, head of school, and Michael Thompson, consulting psychologist, have worked together for ten years at Belmont Hill School (Massachusetts), beginning in the second year of Melvoin’s tenure. For a decade, they have met weekly to discuss the regular psychological issues affecting boys at the school. They have also talked extensively about issues of school leadership. In the following article, they attempt to blend their combined experience into reflections about how heads survive the early years, how they endure the tough times as leaders, and how they can come to thrive in this complex, rewarding role.
PART I:   On Surviving 
WHATEVER EXPECTATIONS a new head of school has, whatever he or she hopes to accomplish, much of the work in the early years has to do simply with surviving. No matter what job a head has held before in a school — or in a different setting — becoming a school head presents challenges you just don’t get elsewhere.
New heads learn this truth very quickly, because the challenges — and adjustments one must make to the challenges — start immediately. In the first week on the job, it becomes clear that the director of admissions and director of athletics are not speaking to each other. Haven’t for a long time. Two weeks before school is to begin, a young teacher walks into the head’s office to explain that he has wanderlust and is not going to fulfill his contract; in fact, his flight to Tibet leaves this afternoon. On the first crisp day of the fall, the main boiler breaks down. That same day, a teacher comes in, agitated, to explain that her mother is terminally ill. Ten minutes later, another teacher comes in, agitated, because the quality of the salad bar at lunch has declined precipitously.

This is hardly hyperbole. The unexpected is the routine.
It’s not just a matter of surviving psychologically, but also physically — actually keeping one’s job. The research indicates that a high percentage of first-time heads come to a parting of the ways with their first schools within the first five years. So part of every new head’s task centers on surviving, on getting through, on getting from one day to the next, from one crisis to the next, from one year to the next. For those who do it, it’s amazing, wonderful, immensely fulfilling work. But how does one cope? What can heads of school do to assure survival in the early years?

Managing Fear

Some fears are legitimate. This is a hard job, and any new head who is not at least a little apprehensive may be heading for a rude awakening. That said, it may be reassuring to realize that many — if not all — new heads have their moments. A story. A new head was having lunch with a veteran school leader, talking through some of the adventures of the first year. The older head confessed that he had spent much of his first two years wondering if he was going to be fired. “Fired? What for?” “Oh, nothing specific,” he said, “but I had no handle on how I was doing, and I couldn’t tell if my work was even close to adequate.” The younger head breathed a sigh of relief. “I have had that same fear going through my head all year.”
Everyone has fears, sometimes deep fears, and all heads can take some comfort in that. Yet, there is reason to keep fear in check. As overwhelming as the job sometimes feels, it is important to look at the other side of the equation: the fact is that schools have a strongly vested interest in seeing a new head succeed. If the new head succeeds, the school succeeds and thrives. By contrast, if this “marriage” does not last, a great part of the burden falls to the school. Certainly the board knows that appointing and supporting a new head is one of its prime tasks. So the board — and administrators and parents and alumni — need to remember how important it is for them that the new head thrives. And if the head needs to remind the board… well, that might be an effort worth making.
Still another way that we all manage fear is to marshal our courage. There are times when courage becomes vital. One long-term head reminds colleagues that some of the defining moments of a successful headship come in that first year or two when one needs to stand up and be counted. A tough stand on a discipline case, a painful move to terminate a long-time faculty member — these may be hard at the moment, but they can set the school, and one’s headship, in a vital new direction. And not taking those steps can cripple a young headship.

Finding Peers and Mentors

The moment a new head arrives at her school she looks around and makes a difficult discovery: she has no peers and no real friends. Having the power to fire and hire is inevitably isolating; it cannot help but shape, to a greater or lesser extent, the nature of the head’s relationships with every person in the building. Every would-be head anticipates this power, yet many are also stunned by the completeness of it. You cannot rely totally on any single administrator in the school in all cases. Indeed, you cannot share the totality of your burden with anyone in the school for the simple reason that you don’t want to unnerve them with respect to your leadership. You may, on occasion, want to share your total bewilderment with your administrators, but you can’t do it too often without losing credibility in front of people whose performance you have to evaluate. 
Heads are not just evaluating the job performance of everyone to whom they speak; they also receive confessions and confidences that cannot be shared. One assistant head, having moved into his first headship, recalled, “I thought my head of school had complete confidence in me and told me everything. We had worked together for years. It was only when I became a head of school myself that I suddenly realized my head had only shared about 70 percent of what he knew.” Faced with holding that 30 percent in confidence, the head looks around for someone outside the building with whom she can speak freely and in confidence. Often, that search leads outside the school to a more experienced head who serves as an informal mentor.
One new head explicitly cultivated a relationship with the long-standing head of a competitor school during the first three years of his leadership. He called his mentor frequently and the older head was both helpful with specifics and reassuring in general. Gradually, the new head split the mentoring work and began calling other colleagues. The younger man felt immense relief at being able to share some of his burdens in these phone calls, and in public he referred frequently to these relationships because they suggested a breadth of experience and expertise. As the years went by, he referenced his mentors and called them less often, evidence of the natural evolution of all mentor/mentee relationships. The mentoring had been vital, and the head emerged with transformed, mutually respectful peer relationships.
A number of new heads haven’t taken the chance of relying on the generosity of other heads or they have not been able to find more experienced colleagues in the area. Mary Worch, the head of The Woods Academy (Maryland), hired an experienced former head, Betty Brown, as part-time assistant head and in-house consultant. Worch says of the relationship with a woman vastly more experienced than she was at the time, “Of course, she was better than me in many ways. You just have to give up being territorial. Betty is so astute in her people skills. She has such a wealth of knowledge and she is so gracious. I used her as a listening board. She didn’t come in to change things and implement her ideas.” After two years, Brown helped Worch hire a new assistant head and stepped into a part-time role in the development office. Worch reports, “I still use her for a listening ear, for strategy.”

The Blessings of Innocence

Part of surviving those first few years comes out of the blessings of innocence, of naiveté, of simply not knowing any better. It is remarkable, and sometimes amusing, how a head gets praised for things for which he or she does not deserve credit — and blamed for things for which he or she is not responsible. One head spoke of gaining great credit, not only from students and parents but also from faculty, for attending several athletic contests during the first fall. The head did not know better; it was something she simply liked to do. What she could not know is that her predecessor never did it — and the difference showed. Then again, that same head was roundly criticized later that fall when she moved the school’s holiday concert out of its traditional place in the local church to an auditorium. Parents and alums saw it as a move toward political correctness and away from the school’s religious traditions; the head had done it simply because the administrative staff reported dangerous overcrowding in the church and had suggested that this would be a good time to change for comfort and safety reasons.
So, one inevitably gets through some issues, with both ups and downs, for reasons that cannot be fathomed ahead of time. Yet, a new head also gets through those early years by remembering the idealism and values that made the board choose him or her in the first place. Sometimes it is good not to know the political landscape, or the sacred cows, not to be too politically savvy.


After saying that she had gotten over her fear of being fired, a young head declared confidently, “If you believe in the mission of the school, you are probably going to be all right. You just have to keep that in the forefront of your mind. That’s the reason for your being. And not all school missions are the same. People think they are, but they are not.”
It is essential for a new head to understand the mission of the school (or discover it, since it is not always well or accurately described by the search committee). Once the mission is clear, the head must define his or her place in it and must — to borrow a phrase from the political arena — stay on message. One head, who entered a school torn apart by serious factional fighting among faculty members, told a visitor, “Oh, I don’t really have a grand plan. I just think everyone in the school should be kind to one another.” Having disavowed that he had a lofty message, the head proceeded to reiterate the theme of mutual respect and “kindness” in every single conversation he had during a ten-hour day using a huge variety of words and stories to illustrate the importance of it. Over and over, he repeated what he thought the school’s mission was and why he thought that consideration for others would advance the mission of the school. The cumulative impact was almost irresistible.

Board Support and the Board Chair

The head’s job is endlessly complicated on a daily basis, and it is all too easy for a head — new or veteran — to get buried in day-to-day efforts. Yet the head has to look at board issues and needs, at long-term issues, if he or she is going to lead the school successfully. Thus, another critical part of surviving the first years of a headship comes from having a supportive board — and especially a supportive board chair. Whether a board is composed of ten people or 40, the fact is that the head needs to be able to call one person — the board chair. And it is okay to ask for support, institutional or personal. One weary head made yet another call to his board chair in May of that fateful first year. “John, I am afraid I have another personnel issue for you.” The board chair laughed and said, “Well, they are all personnel issues. Let’s get to it.” Another trait of a good board chair is accessibility. What a blessing it is to a new head to have a board chair who reminds the new head that he or she is always available and who backs that up: who takes the tough calls, who makes time available, who asks how the new head is faring.

A Life Outside

One of the virtues of working in an independent school — and one of its great risks — lies in letting energetic, multi-talented people dive into a wonderful range of activities. This is true of the head as well. It is all too easy for a conscientious new head to work 60- or 70- or 80-hour weeks, and it may be hard to tell him or her to stop. One way for a new head to survive is to have friends and activities that have nothing to do with school. That may be tougher for a head who has just moved to a new city or town, but it remains no less important. The head who joins a tennis club or a local chorus, coaches a child’s soccer team on Saturday morning, and gets involved with church or temple or mosque: any of these can open up some lines of contact, and healthy activity, with people who know blessedly little about a head’s school. It may be heartening to remember that the school does not even exist in the minds of many people who may live even in the same neighborhood. One head religiously plays basketball every Sunday morning. He has broken his collarbone, rolled his ankle; he limps into school most Monday mornings. But he does it with a smile, for he has cleaned out the pipes, playing as hard as he can with a bunch of guys who are bankers and electricians, dropouts, and Ph.D.s, all of whom could care less about what he does the other six days a week. Such a complete break from the world of school is refreshing — and invaluable.
Part II: And Sometimes Enduring
WITHIN SEVERAL HOURS of the death of a ninth-grade boy in a car accident, the head’s office is filled with crying students and faculty members. Filled with her own grief for a boy she had known since kindergarten, the head nevertheless has to comfort her students, rally her faculty, organize her administrators to implement a crisis plan and drive over to see the distraught family of the boy. Within days, she also has to schedule conversations with her lawyer to help her deal with the police and the local district attorney, who is considering prosecuting the two seniors who were driving the car while under the influence of alcohol at the time.
Why do we use the word “enduring?” Because a head doesn’t just move from surviving to thriving; it’s not that simple. Stuff happens. We’re not just talking about hard work and long hours; those are given, for a head of school. There are times when, even if the head finds he is good at the job and "loves" it, the burden of the position must be borne, and borne almost alone. When an hour before the graduation ceremony the head receives a call that a boy’s father has just died and he is asked to notify the boy; when a disturbed family files a baseless lawsuit that the head knows is going to preoccupy her, possibly for months; when the head hears that all the senior class is rife with rumors about a young faculty member having sex with a graduating senior after a drunken graduation party; when something shameful and unfavorable about the school appears in the local paper, the head’s heart sinks and she knows she is entering a period of endurance. How long it will last, no one can say. At those moments, the job is not just hard: it is psychologically painful. What gets a head through these periods? 

A Trusted Administrative Team

City kids sometimes say about a friend, “He has my back.” It is during the times of endurance that a head discovers whether his administrative team “has his back” — that is, exactly how deep the trust and support of his or her administrative team runs. The school obviously requires good administrators every day, year-round, and it is the head’s job to hire them and help them work well together. A head may be able to tolerate a decent or even mediocre administrator for a period of time, someone who needs, perhaps, to be counseled out in the next year. At times of crisis, however, the head needs a group of administrators he or she can trust completely. That does not mean that the head needs to be surrounded by “yes” men and women. His or her administrative team should disagree with the head, if the team members are so moved, and they should come up with creative ideas that the head cannot at that moment. It is, however, essential for there to be trust and camaraderie in a crisis.
If there is one vital reason to pull the plug on a weak administrator, or to work hard to pull a fractious administrative team together, it is because the head will need the entire team to help pull through a tough time. If a head does not have such a team around him or her, it is the head who may end up leaving the job.

The Board Chair

We noted the importance of having a supportive and available board chair to help a new head through those early years. The need endures, even as a head strives to endure. And endurance, over time, takes effort.
It is worth remembering that, from a structural view of governance, schools are strange beasts. Many independent schools have parent-dominated boards with relatively brief terms, of two or three years, and strict term limits. Thus, it is possible for a “still new” (or feeling "still new") head of five or six years' tenure to look up and realize that virtually all of the trustees who appointed him or her are no longer on the board.
Who can help the head endure? A strong and supportive board chair can make a huge difference, offering steady support over time and through change. However, in a long headship, it is the head who has to take the lead in recreating a close, even intimate relationship with a new chair. The late Earle Harrison once reported that, in his 30 years as head of Sidwell Friends School (Washington, D.C.), he had 16 board chairs. That’s a lot of relationship energy for the head to generate! Inevitably, a veteran head will stumble into a board chair who is awed by the head’s skills or length of tenure. “You’re an experienced head,” one new board chair told his head at their first lunch together, “I’ll just try not to screw things up. I’m happy to run the board as long as you are the head.” The head who received that remark felt both flattered and depressed by it. His internal reaction was, “Oh great! Who is going to take care of me?”
But because board chairs inevitably change, the head needs to do more. Even if the board does not want to spend time on this, a head hoping to endure needs to push the board to examine goals — for everyone’s sake. So too does a head need sometimes to push a board for helpful, timely, appropriate evaluation. The more evaluation that takes place, the less burdensome and threatening the process becomes for both sides. The more evaluation that takes place, the more constructive it can be, again for both sides. In these ways, a head makes sure that he or she is never too far off from the board’s goals, never too far ahead of the board.

Family and Friends

While structured, professional trustee support is vital, so is personal support. The head’s job is simply too difficult without the help of friends and especially family. To endure, the head needs to remember that family must always come first — for, if it doesn’t, it may not be there when he or she needs it most. So, the head needs to support the family. One head had to miss a year-end school assembly because his daughter had her own year-end program, and he was not going to miss it. That was not only a right priority; that was good role-modeling. By the time a head is a few years into the mission, he or she has got to be able, within reason, to control the daily calendar, the number of night meetings, and the number of essential weekends. A board might not love all absences, but a board would rather endure a few absences than have to find a new head. No matter how much the parents advisory group or the development office pushes, a head must retain the right to say no. Claiming a night each week can offer the promise of some regular sanity. One head we know used to play banjo every Tuesday night in a Dixieland jazz group. The school knew where he was — and that he was not available for that night. And, of course, the school adjusted. Whether the head and spouse reserve it for a “date night” or whether the head uses it for a weekly yoga session or book club, such bouts of sanity can help a head endure.
Some of this is about love and support; some of it is simply protection. No two heads are exactly alike. Some need more personal space than others; some have their needs change over time. One head recently confided that she needed to recreate her headship; she simply did not have the energy she had when she began 15 years ago. Then again, she added, she is a lot smarter and stronger than she used to be, so the act of reinventing her headship was actually quite healthy, even exciting. Another head spoke glowingly about how much his administrative team grew when he was on sabbatical, and how that enabled him to have a different, and better, headship post-sabbatical. 
Part III: Thriving
AT ONE OF HIS GOOD-BYE PARTIES last spring, which included all of the young heads of school in the greater Boston area, Tony Jarvis, retiring head of The Roxbury Latin School (Massachusetts) stood up and began his talk with the sentence, “This is the greatest job in the world.” Well, we might demur, it is a great job, but it is not for everyone. For some heads, the job clearly overwhelms their gifts, others get beaten up on the job, or they discover that they simply do not enjoy it. One discovery that some heads make in the early years is that this is just not the job for them. On the other hand, some long-serving heads of school are among the happiest people we know, taking into account all professions. What are the secrets of thriving as a head of school?

Adapting and Adopting

No school finds the perfect head and visa versa. One head described the headship process in the following way: “The search committee and I romanced each other. They didn’t tell me everything about the school and they didn’t learn all they might have wanted to know about me. That has made the marriage a bit rocky, but we’re staying together for the sake of the children.”
This head has humorously described the keys to enjoying the job: adapt to what you find and adopt the community as your own. School communities don’t embrace heads of school who aren’t enjoying the job of leading the school community. Simply working very hard at the job is not enough to make you thrive in the work. You have to adopt the school as your own; you have to make it your baby. If you cannot do that, you should leave sooner rather than later, because the community can sense it. If you find yourself dreaming about another type of school, that should be evidence that you are not going to be able to adopt your new community.
If you do, however, manage to adopt the school in your heart, you will suddenly feel lucky to be there. Everyone in the community immediately divines that you have made the internal commitment.

Balance/Pace/Rate of Change

We once heard a veteran head remark that any head brings change to a school. Whether consciously or not, change occurs: sometimes because problems or issues force change, sometimes because a head initiates them, sometimes simply because of the head’s persona and style and values. A key to thriving as a head, then, comes from understanding change and directing it. What is a school’s culture all about? What are the key values, the essential traditions? How really invested is the board in change? At what pace should change come? Sometimes schools need to take big steps, firmly and quickly. Other times a school needs to move slowly, to take only incremental steps. Judging both the changes themselves and the rate of change requires a certain deftness from the head, a certain orchestration, even some artistry.
There is no magic to this; like good art, it requires discipline and hard work as well as creativity. One head recently confided that one of his goals for the year — and this in a thriving headship and school — was to not initiate anything new in the year ahead. “We have had so much change of late, and people have been asked to do so much, that we need a year where the goal is ‘steadiness.’” Another head, remarking on the traumatic loss of a beloved teacher at the end of the previous year, felt that the school was still too tired emotionally to engage in some new initiatives in the year ahead. Each year is different, and a thriving head remembers that when trying to balance stability and change.
Even as a head strives to understand and measure change, so too does he or she need to remember that there are some things one can control — and many things one cannot. A pivotal moment in one head’s tenure came when she was talking to a 20-year veteran colleague, explaining how she felt pressure to make sure that each year was “the best year ever” for the school. The veteran head stared back. “But you can’t do that. You do not have the power to control all that happens in your school. There can be problems, even disasters, that are not your fault. All you can do is to do your best to help the school through those tough times. The school year may not be a great or happy one, but you cannot will that. You can only control what you can control.” As Clint Eastwood’s Dirty Harry once famously said, “A man has got to know his limitations.”

A Great Administrative Assistant

When we told Connie MacGillivray, Rick Melvoin’s administrative assistant, that we were writing a paper about “surviving, thriving, and enduring” as a head, she looked up and said, “And you have talked about the role of the administrative assistant, haven’t you?”

Constantly Articulating Your Personal Mission

A gifted psychoanalyst once taught us that you must keep asking a patient, “Why are you still coming?” in order to constantly refocus the treatment. If you follow an experienced head around for a day, you will discover that he or she is always answering the silent question, “Why am I still here?” A successful head is always refining his personal mission and how it relates to the school’s mission. When Todd Horn, head of Kent Denver School (Colorado), walks a visitor around his school, he discusses in a matter-of-fact way what he did in the first five years and what he is intending to do in the future. If you talk to Tom Northrup at The Hill School (Virginia), he’ll describe the three different phases of his 20-plus-year headship. It happens naturally, casually, yet it provides crucial evidence that the head is still growing. It is this constant redefinition of self and mission that we hear from school heads who are thriving.

Creating Fun for Yourself in the Job

It is axiomatic among heads that when you need a morale boost, you go down to the kindergarten to read them a book. It is a total win-win-win situation: for head, teacher, and kids. The head gets to bathe in the glow of kindergarten admiration and forget his troubles for 25 minutes. So many heads have discovered this tonic that it is recommended to new heads over and over. But why stop there?
We asked a long-serving headmaster once how he was able to stay in such good physical shape (and why his tennis game seemed so tuned up.) “I’m the head,” he said, “I have my administrative assistant schedule me to practice every afternoon with the girls’ varsity tennis team.”
A California headmaster turned the most dreaded part of the day at many schools — car pool — into his own personal circus. He used an outside microphone, called out the name of every parent who drove up, matched them with their children, and directed cars with firmness and good spirit. It sounded like an auction or someone calling the Kentucky Derby. There was no doubting that the head was having a blast doing it.
Don’t try to get Mark Segar to leave the Waynflete School (Maine) on Wednesday mornings. That’s the day for the Pachanga, when the entire elementary school meets in the gym to sing, and where the headmaster plays the guitar.
Is the head’s job “fun”? Parts of it, one hopes, at least part of the time. One of the great things about heading an independent school is that the scale is relatively small and, thus, the contact with all elements of the organization is extensive; even most large independent schools are not very large compared to their public school counterparts. Does that make the job more demanding? Of course. Is having an enthusiastic group of volunteer trustees overseeing a school’s governance a mixed blessing? Yes. So, too, the tradeoffs of having parents who are smart, concerned, involved, opinionated — and who are paying for the privilege of being engaged in the school. So, too, the reality of different constituencies constantly requiring attention: students, faculty, staff, parents, alumni, trustees, local authorities, and the broader community. So, too, the realization that every day is different — or might become different in the blink of an eye. 
That which makes the head’s job complex is also what makes it fascinating and can make it wonderful. A head needs to remember the fascinating/wonderful/ growth side and embrace it through the tough times. But if a head is willing, that passage from surviving to thriving can indeed come — even with the inevitable bouts of enduring — and can make this as rewarding as any job can be. Remembering that leadership of a school means the shepherding of a new generation of young people into the world. There is no more important job in the world. And that gift, that opportunity, makes it all worthwhile.
Michael Thompson

Michael Thompson, Ph.D., is the consulting psychologist to the Belmont Hill School in Belmont, MA. He is the author of nine books and many articles, including Raising Cain: Protecting the Emotional Life of Boys, and Best Friends, Worst Enemies: Understanding the Social Lives of Children.

Rick Melvoin

Rick Melvoin is the head of Belmont Hill School (Massachusetts).