The New Career Path for Headmasters

Then and Now

A Major Board Decision. Photo © Nick Cowie

The route to the headmaster's office has changed. Once upon a time, the headmaster, often referred to as 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 connected and respected within the community.

However, in an increasingly competitive marketplace with higher expectations placed on schools, the profile of the head of school is 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 teacher, coached your team sport, kept your nose clean, married acceptably, raised some children of your own, became dean of students, and after 15 or 20 years you were in the running for head of school.

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 '90s, however. Years ago, it 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

Many people first acknowledged this shift in the summer of 2002, when Mayor Michael R. Bloomberg of New York City surprised the masses 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 brought vast business experience to that most complicated of assignments.

His appointment served as a wake up call to the educational establishment as a whole that new and imaginative approaches to school administration are needed. This was only the first step in what soon became a rapidly changing environment. 

Private schools shifted from viewing themselves solely as academic institutions to operating under dual roles: schools and businesses. The academic side of operations continues to grow and flourish with the changing times, often faster than the business side of these elite institutions. However, heads have begun to acknowledge the need for augmented admission offices to recruit students, development offices to raise money to support school operations, and business offices to better manage the daily financial needs of schools and their communities. The need for strong marketing and communications has also become apparent, and continues to grow rapidly, with schools employing large offices of skilled professionals working to develop new target audience.


The new head's role isn't to simply ensure that everything plugs along in terms of day to day tasks. But rather, the new head is responsible for leading a powerful group of professionals who are working to ensure that the school thrives in difficult and at times, downright volatile market conditions. While the head isn't expected to know how to "do" everything, he or she is expected to provide clear and concise goals and strategic vision. 

The biggest, and often hardest change for many to swallow is the need to see families as 'customers' and not only as parents of students with malleable minds which need solid training, nurturing and direction for success in later life.  

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 strategic leader and 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. 1, 2018, Kennedy, Robert. (2018, March 1). The New Career Path for Headmasters. Retrieved from Kennedy, Robert. "The New Career Path for Headmasters." ThoughtCo. (accessed March 24, 2018).