The New Career Path for Headmasters

Then and Now

A Major Board Decision. Photo © Nick Cowie
The New Career Path for Headmasters

The route to the headmaster's office has changed. Once upon a time the head of a school was almost certainly somebody with teaching and administrative experience. Better yet he or she was an alumnus or an alumna - an old boy or an old girl. Well, that's changing. To be sure, it's a gradual change. But it's a change nonetheless, and it's occurring because the challenges facing a head of school these days require experiences and skill sets not usually found in a person who is first and foremost an educator.

The Way It Used to Be

For years the way to the top of the private school organization chart was through the hallowed halls of academe. You graduated from college with a degree in your subject. You were engaged as a third form master or whatever, coached your team sport, kept your nose clean, married acceptably, raised some children of your own, became dean of students, then deputy head of school, and after 15 or 20 years you were in the running for head of school at St. Swithin's.

Most of the time that worked just fine. You knew the drill, understood the clientele, accepted the curriculum, made a few changes, tweaked the faculty appointments ever so slightly, steered clear of controversy, and magically, there you were: receiving a nice check and being put out to pasture after 20 years or so as head of school.

The Way It Is Now

Life got complicated in '90's. Used to be that the head could run his school simply by looking out his office window and observing what was going on.

A periodic look in at the faculty lounge and an occasional meeting with alumni and parents to raise some money - it all was pretty straightforward. Even a bit dull. Not any more.

The head of a private school in the new millennium has to have the executive ability of Fortune 1000 executive, the diplomatic skills of Ban Ki-moon and the vision of Bill Gates.

S/he has to deal with substance abuse. S/he has to be politically correct. His graduates have to get into the right colleges. He has to raise millions for this project and that. He has to sort through legal issues which would numb the mind of a Philadelphia lawyer. He needs the diplomatic skills of an ambassador to deal with parents. His technology infrastructure costs a fortune and doesn't seem to have improved teaching at all. On top of all this, his admissions department now has to compete for students with several other schools which years ago could hardly be considered the competition if they existed at all.

CEO vs Educator

In the summer of 2002 Mayor Michael R. Bloomberg of New York City surprised many people by appointing a lawyer/executive with no formal educational administrative training as Chancellor of the New York City schools. As CEO of the Bertelsmann, Inc. media conglomerate, Joel I. Klein brings vast business experience to that most complicated of assignments. His appointment serves as a wake up call to the educational establishment as a whole that new and imaginative approaches to school administration are needed.

The Opposing View

The flip side to appointing a 'CEO' as head of school is that s/he may see students as 'customers' and not as young people with malleable minds which need solid training, nurturing and direction for success in later life.

S/he may alienate parents and alumni and diminish the overall financial support of the school if s/he adopts a management style which works in the corporate arena, but is ill-suited to the academic environment. Often that approach backfires with tremendous embarrassment and damage to the school.

3 Questions to Ask

  • If your school is searching for a new head of school, is it looking 'outside the box' or seeking to perpetuate the existing administrative philosophy and practices?
  • Does the school community believe that change is even necessary in order for the school to survive or does it cling desperately to the status quo?
  • Has your school developed and implemented a strategic plan?
Characteristics to Look for

Choosing the right head is critical part of moving your school successfully through changing circumstances and financial tough times.

Given the large number of constituencies within a school community you will need to find a consensus builder.

A good head listens well. S/he understands the widely differing needs of parents, faculty and students, yet demands the partnership and cooperation of all three groups to accomplish his educational goals.

S/he is a skilled sales person who has a solid grip on the facts and can articulate them convincingly. Whether s/he is raising money, speaking at a seminar in his area of expertise or addressing a faculty meeting, s/he represents and sells the school to everybody s/he encounters.

A good head is a leader and an exemplar. His vision is clear and well thought out. His moral values are above reproach.

A good head manages effectively. S/he delegates to others and holds them accountable.

A good head doesn't have to prove himself. He knows what is required and accomplishes it.

Hire a Search Firm

The reality is that to find this person, you may have to spend some money and hire a search firm to identify suitable candidates. Appoint a search committee which can include trustees as well as representatives from your school community such as a student, a faculty member and an administrator. The search committee will vet the applicants and present a candidate for the board of trustees' approval.

Hiring a new headmaster is a process. It takes time. If you do it right, you have charted a path for success. Get it wrong and the results could be just the opposite.

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Your Citation
Kennedy, Robert. "The New Career Path for Headmasters." ThoughtCo, Mar. 3, 2016, Kennedy, Robert. (2016, March 3). The New Career Path for Headmasters. Retrieved from Kennedy, Robert. "The New Career Path for Headmasters." ThoughtCo. (accessed January 17, 2018).