Why the Increase in Head Of School Turnover? | James Wickenden | 8 Min Read

In 1942, my father was appointed Headmaster of Tabor Academy, a school in Marion, MA, with an enrollment of 42 boys. (The job title “Head of School” was not used at that time.)  For 36 years my father and his colleagues gradually increased the enrollment to 550.   Also of note was the fact that during the last seven years of his Headship, he refused to accept a raise, preferring instead to have whatever monies were available to go to the faculty.  Why do I begin this article by mentioning my father?  After 36 years of leading Tabor Academy, the Board of Trustees informed him that he would be replaced.  Although age, not a pandemic, was responsible for that change, the issue of turnover amongst Heads of School is not a recent phenomenon.

It is now over 45 years since my father was informed that he should retire. Because my memory of his being relieved of his responsibilities still lingers, that combined with multiple stories during the 2020-21 academic year about the turnover amongst the Heads of several independent schools, prompted me to write an article that would not only describe how challenging the job of a Head of School was and is, but also how a confluence of issues resulted in multiple resignations, retirements, and non-retentions. 

At the risk of stating the obvious, the job of a Head of School is incredibly challenging.  For example, it was not uncommon for Dad to:

  • Go to the office at 5:00 a.m. to dictate letters.
  • Go to bed at 10:00 p.m. after hearing from the dorm masters that everything (presumably) was under control.
  • Attend breakfast, lunch, and dinner in the dining hall with all of the students and the faculty.
  • Visit students in the infirmary who were sick.
  • Be visible in the academic center when students changed classes.
  • Serve as the conductor of the Glee Club.
  • Attend practices and games of the various athletic teams.
  • Preside over meetings with the students following dinner.

Complicating every Head’s life both then and now is the necessity of dealing with the unexpected.  Examples of this include:

  • Disciplining a student who was accused of stealing.
  • Conducting an investigation regarding alleged sexual molestation.
  • Expelling a student who is the offspring of a trustee, major donor, or good friend of the school.
  • Managing a crisis delivered by Mother Nature, be it a hurricane, fire, or flooding.
  • Turn around a disgruntled alum who is a potentially large donor.
  • Returning calls from angry parents, alumni, or even other Heads of School.
  • Managing responses in a faculty meeting from those who were disgruntled.
  • And worst of all, serving as the leader of the school following the death of a student, faculty member, trustee, or parent.

While the aforementioned challenges faced by most Heads of School are considerable, they pale by comparison to the complications many, if not most, Heads of School encountered during the 2020-21 academic year.  The following examples may not apply to every school, but they certainly complicated the lives of many Heads who had to respond to situations for which they were never trained or experienced.   For example, in just the past two years, the Heads had to:

  • Manage a pandemic, which included virtual and hybrid learning, adjusting to social distancing, canceling athletic and other events, while simultaneously responding to the conflicting comments of disgruntled parents and anxious faculty members.
  • Respond in a meaningful and constructive fashion to the deaths of George Floyd and other Blacks.
  • Address the legitimate concerns of people of color in the school community that had been overlooked for years.
  • Deal with worried parents who legitimately believed that the recent changes in college admissions policies adversely impacted their children.
  • Set standards with respect to the students’ use of social media.

In sum, Heads of Schools were expected to deal with some or all of the aforementioned issues with little or no guidance.  Making matters worse, we have heard stories about angry parents who wanted schools to be open rather than having virtual learning, about students struggling with depression, about adolescents and young adults acting as if their definition of social distancing was one foot, not six feet, and about the resistance of some teachers and families to getting vaccinated for Covid-19 and its variants.

Many of the school’s constituents looked to the beleaguered Heads of School for solutions to these complex problems.  It is difficult enough to lead an independent school under normal conditions, but it was nearly impossible for these stalwart leaders to manage anxious and demanding trustees, critical teachers, worried parents, depressed students, and possibly families from other countries.

While being a Head of School can be rewarding, I’m nonetheless convinced that leading a school is incredibly challenging and at times woefully difficult. It’s even more difficult now because of the aforementioned conditions that Heads have experienced. As Andrew Watson, the former 19-year Head of School at Albuquerque Academy, recently stated,

“While in the past, the cause of Head turnover was linked to the skills/performance of the Head and/or the effectiveness of the Board, the most profound new factor is how the community treats the Head.  According to some Heads, the abuse they have taken over the past two years is incredible. Trying to thread the needle on COVID (open/closed) amidst changing guidance on social justice (too much/too little) is almost impossible, and the anger from school communities is shocking.”

Andrew Watson, the former 19-year Head of School at Albuquerque Academy

What might be done to reduce the turnover amongst Heads of School, as well as the tension within schools that has made life difficult for all of the different constituencies?  While there is no easy or simplistic answer to that question, I’ll nonetheless venture into this space.

 I’ll start by recommending a few changes that Boards of Trustee might consider.

  1. With some exceptions, Boards do not communicate well with the different constituencies of the school.  Nonetheless, communication from the leadership of the Board to the different constituencies of the school is essential. Policies can be debated and codified before they are shared with the faculty, staff, and parents.  Behaviors by any member of the school family that cannot be tolerated need to be defined, communicated, and enforced. The ideal culture of the school should be put in writing and used as a baseline when members of the school community need to be confronted. When appropriate, the annual goals of the Board, the Head, and the different departments of the school should be shared with the school community by posting them on the school’s website.
  1. Attention should be given to developing criteria about the skill sets and experience needed by those on the Board.  Having served on nine different Boards of independent schools, I readily admit that I failed to argue successfully about the need to recruit men or women who, for example, are health care professionals, have an expertise in the arts, a knowledge of technology, or experience as a teacher or former Head of school. Granted those are not the only qualities that could be sought, but they were absent from many of the Boards on which I sat.
  1. Attention should also be given to establishing a committee structure on the Board that would best serve the needs of the school.  What is not necessary is a committee structure that duplicates the administrative structure of the school.  Is there a need for a committee on inclusivity?  Is there a need for a committee that addresses initiatives that would improve safety?  Is there a need for a committee that deals with the professional development of those who work for the school?

Next, what might be done with respect to the administrative structure of the school?

  1. Every Head should have a work ethic that is respected.  That being said, the work done by the Head should be focused on the mission, critical needs, and goals of the school. Some of these responsibilities require a fair amount of attention; many, however, could be delegated. Issues that are not of the highest priorities could be delegated to one or more of the direct reports to the Head.
  1. At the end of the academic year, the administrative leadership of the school should be convened and charged with the responsibility of identifying the problems or crises that were experienced, how they were handled, and in some cases define what should be done to produce a more effective response. 
  1. Undeniably, 2020 and 2021 presented the leaders of independent schools with multiple challenges.  We hope that the future will not be defined by a pandemic, a presidential election that divided the country, policing practices that resulted in the deaths of people of color, significant increases in “deaths of despair”, colleges and universities changing their admissions policies and practices, mass shootings, and the deaths of over 500,000 people in the United States who contracted the COVID-19 virus.  Schools cannot prevent any of these problems from reoccurring, but they might act on the adage of “Hope for the best while planning for the worst.”  One planning option might use the human resources of the school to create a Safety Committee composed of knowledgeable people (e. g. the CFO, the Director of Buildings and Grounds, the Director of Technology, the school Nurse, a lawyer, and a parent or trustee in the construction business.)  While no school will be able to defeat Mother Nature if she decides to vent her wrath, those on a Safety Committee might be able to minimize damage.

In sum, many of us, but particularly those leading schools, have been caught in the past 18 months in a social typhoon that resulted in many Heads admitting to being exhausted from dealing with behaviors that were characterized more by anger than respect, being confronted by problems to which there were no ready solutions, and being led by trustees who sent mixed messages but withheld support.  As a result, many Heads of Schools for whom I have enormous respect have either resigned, retired, or have been informed that they would not be reappointed.  

Those Heads who have left or will leave a job and school that they loved, improved, nurtured, and changed, will be missed and, I hope, be recognized for the efforts they made to exercise control over a set of conditions that none had ever before confronted.

Jim Wickenden

Jim is a Principal at DRG and Founder of Wickenden Associates, an affiliate of DRG. Having been the CEO of one of the premier education executive search firms in the United States, Jim brings unparalleled experience and networks to best serve clients.With over 30 years of experience identifying and guiding Heads of Schools and other senior administrators of schools across the country, Jim approaches each search with flexibility and openness that responds to the individual needs and concerns of schools and their leaders.Before founding Wickenden Associates, Jim served as the Dean of Admissions at Princeton University and Director of Student and Alumni Affairs at the Harvard Graduate School of Education. A graduate of Tabor Academy and Princeton University, Jim holds a master’s degree in Counselor Education from Rutgers University, a master’s degree in the General Purposes of Education from Harvard University, and a doctorate in Counseling Psychology from Boston University.As a former member of eight boards of independent schools with a wide range of missions and resource levels, Jim also knows firsthand the responsibilities shouldered by today’s trustees; and knows how to guide boards through tough transition processes and on good governance practices.Jim lives in Princeton, NJ, and when he is not at the office he enjoys reading enlightening books.

2 thoughts on “Why the Increase in Head Of School Turnover? | James Wickenden | 8 Min Read

  1. I would contend that the turnover has a lot to do with many current heads not having the “chops” needed to meet a rapidly changing market. Schools keep turning to the same old, same old profile for a head of school when the schools have different needs than 20 years ago. My job is hard but deeply satisfying, and thank goodness I don’t have to conduct a glee club!

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