top of page
  • Pam Clarke

Why Being a Head of School is so Hard... OOPS, I Mean FUN!

Updated: Feb 20

The Head of School is responsible for everything that happens or pertains to the independent school; search professionals looking for Head replacements joke that the school wants “God on a good day.” Trouble is, it’s not a joke; that is what they want.

The Facts

The Head of School’s employment contract runs 25 or more pages these days and lists the Head’s responsibilities on about half of those pages and reasons to be fired or ‘let go’ on the other half. In the past dozen or so years, the doors for Heads of School seem to be the revolving type.

In a 2019 study done by NAIS with The University of Pennsylvania Graduate School of Education, about one in five new and interim Heads of School that year followed a head who had held the position for three years or fewer and nearly one in three schools in this survey reported having had three or more heads of school in the past 10 years.[1]

Item #1

Boards and Heads are losing contact

The pandemic has increased stress for both Heads and their boards, and the issues of

DEIJ/belonging following the death of George Floyd have fractured school communities. In these challenging waters, Boards and Heads are not sure who is holding the tiller… Boards and Heads seem to be losing contact with each other.

For example, 70% of boards said that they have a transition process in place for new heads of school, but only 55% of these heads were aware of this process. Further, over 80% of boards agreed that, during the search for a new Head, their school focused on long-term sustainability (rather than fixing a specific problem), but only 62% of heads agreed with this, and 31% were unsure. This math is troubling and would seem evidence of the tenuous relationships between Heads and their Boards right from the start – even during the search process.

Item #2

The Board Chair and The Head (May) Have a Poor relationship

One major indicator of the health of an independent school is the strength of the relationship between the Head and the Board Chair – the former is quite well-paid and very well-trained, and the latter is a well-meaning volunteer with expertise in many fields but not often education. My best Board chair called me 2-3 times a week and was the consummate listener; the Head job is lonely – every person the Head sees either works for the Head or is a paying customer; and that phrase by itself is evidence of the single largest change in Independent Schools.

Gone are the days when families worshipped their Heads, when alumni all but genuflected at reunions and when the Head of School was the last word on all things academic and financial – reference Frank Boyden whose 66-year term as Head of Deerfield Academy is unparalleled – he who kept his desk in the hallway of the Main Building so as to keep the pulse of the school. Even Deerfield has had five Heads in the 54 years since Mr. Boyden.

Item #3

The Speed of Communication in 2023

There are multiple constituencies to manage: students, their parents, alumni/ae, teaching faculty, administrators, school staff, the members of the town’s council, neighbors of the school, vendors, contractors, and more. Managing so many relationships and answering to so many disparate interests is challenging, and the challenge is enhanced by the speed at which people expect answers and replies. The speed of email and text is a major culprit—a parent may get information about an incident in the classroom well before the Head has heard a thing. Because information can be processed and sent in seconds, people expect schools to do it. Add the expectation of a speedy response to the number of people in the many constituencies, and the Head is often besieged and overwhelmed – unbeknownst to anyone else! The constant demand for answers, information, and/or opinion wears on one’s enthusiasm and erodes one’s apparently boundless energy.

Item #4

The constant threat of legal action

After the Board chair, the Head’s second-best friend is the school’s lawyer; it is not surprising that the rush to sue that has hit every segment of the business world now includes schools and other not-for-profits. Suits have been threatened to get a higher grade in a class, to be remunerated for a broken wrist on campus, and to be arrested for allowing a delivery to the school before 7:00 AM. (How does one prove that something did not happen?) With due respect for any charge of negligence, the nuisance suits take valuable time and energy - costly by their very existence.

So, why do we do this?

It’s so much FUN to see and hear a five-year-old realize that all those marks on the page represent sounds with meaning; to watch the six-year-old write and draw a Mother’s Day card; to see the second-grade bottle rockets head for the stars; to take the third graders mushroom hunting in the woods; to receive the lower school council’s request for chocolate milk – at least on Fridays.

To chaperone a middle school dance is an exercise in amusing frustration; they twist and gyre and pretend to be having fun; they worked so hard on decorations and permissions; the reality can almost never live up to the hype. By high school, such dances are really fun; watching the basketball star dance with her friends or the debate winner sing at the karaoke stage is a true testament to the variety of adolescent experiences.

It's not all fun and games; the teacher whose husband has gone to rehab; the parent whose child has to have chemotherapy; the ninth grader who has felt the need to cheat – there are personal and often public challenges that the Head must mitigate and manage. The best training one can have for this job might be a degree in counseling and human development.

In addition, the board's understanding of our job and their role in our success is paramount. Well-trained boards make for a successful school and make our lives so much more manageable.

It can help to bring in a professional (such as me) to bring your board to the fullest understanding of the job and their roles.

Just imagine!

1) Improving lines of communication between you and your Board

2) Increasing the Board's understanding of the complexity of the way a school functions

3) Increasing trust between you and your Board

I love the fullness of this job – it’s perfect for an ADD workaholic – something different every few minutes and as disparate a set of demands as one can imagine – a hundred things to do today, and I love getting up tomorrow to do it all again!

And being Head of School is the very finest opportunity to exercise what Neil deGrasse Tyson reminds us are the four constants in this world: Love Kindness Integrity and Honor.

If improving communication and trust with your board sets off a spark, let's have a chat. Email me here:

[1] In summer 2019, 466 heads of school, 108 board chairs, and 247 board members at NAIS

schools anonymously completed the 66-question NAIS-UPenn Survey on Factors Affecting

76 views0 comments
bottom of page