Head of School Aphorisms

In a recent exchange with former student Jason Warnick, Hyde ’98 and currently head of school at Wayland Academy (Beaver Dam, WI), we got to swapping timeless quips and quotes we had heard, read, or have been attributed to school heads over the years. After we said our good-byes, I got to thinking… (Being half-way through a rigorous chemo regimen, I’m doing a lot more of that while puttering around the house alternating between treatments and recovery.) Thought I’d serve up 10 aphorisms that helped me during my own 30+- years (1987-2018) as a head of school.

1. “… The greatness of the private school, Brian, is not that it produces geniuses — but it can sometimes turn a third-rate student into a second-rate one. We can’t boast publicly of such triumphs, but they are still our glory.” – From The Rector of Justin by Louis Auchincloss (Houghton Mifflin, 1964)

This book, fiction informed by the life of Groton founder Endicott Peabody, is one leg of what I call “The Headmaster’s Trilogy,” the other two being John McPhee’s The Headmaster, a 1966 bio of Deerfield’s legendary Frank Boyden, whom I have referred to as the Babe Ruth of heads of schools. (If you attended or taught at any boarding school, you were influenced by him and you might not even know it.)… And Richard Hawley’s The Headmaster’s Papers (2002). Speaking of Boyden…

2. “I never reprimand a boy after dinner because darkness and a troubled mind are a bad combination for a teenager.” – Frank Boyden, headmaster of Deerfield Academy from 1902-1968 (And those dates are not a misprint!)

When I first read that quote decades ago, I remember thinking: Wow! I don’t even know if that’s true, but I do know that this guy thought on a wholly different level than I am. Maybe I need to consciously try to raise my own thinking game to a deeper level.

3. “Anyone who is leading a small college* is actually running something that is a cross between a faltering corporation and a hotel.” – Leon Botstein (President of Bard College – NY – 1990-Present)

*I substitute “typical boarding school” for “small college,” as the same principle applies. Or, to put it another way, You can’t fix the place up until the people (i.e. tuition-paying customers) come, but the people aren’t gonna come until you fix the place up. Therein lies the Catch-22.

4. As I was starting as head of school, I read an interview with Yale president Kingman Brewster (1963-77) where the reporter asked what is was like to lead such an esteemed institution of higher learning. Brewster off-handedly replied (the best quotes tend to come that way!), “There are days when I feel as though I’m conducting a beautiful symphony orchestra, but on most days I feel like the clutch on a truck.”

I recall thinking, That’s an apt description of my job!

5. “Your fast ball works a lot better if you throw in a change-up from time-to-time.” – Bill Clough (head of school at Gould Academy – Maine — 1983-2001)

This one might be filed under Emerson’s “Consistency is the hobgoblin of little minds” quote. Perhaps more than any other head of school, Bill and his wife, Ki, were valued mentors for Laura and me. We sought to emulate them more than they know.

6. “It is perhaps unfortunate that tolerance has evolved into the supreme virtue of our age.” – Reverend F. Washington “Tony” Jarvis, III (head of school, Roxbury Latin – MA – 1974-2004)

I heard this many years ago while attending an educational conference for school heads in Boston where Tony was a keynote. Perhaps the best way to explain it is with an excerpt from my 2023 book Culture by Design:

… His remark captured everyone’s attention to an extent that reminded me of those E. F. Hutton commercials of old where, upon hearing the words “E. F. Hutton,” everyone in a large room of people stops whatever they’re doing and begins listening for more information.

Tony let the message sink in for a bit before continuing (and I’m paraphrasing from a thirty-year-old memory): “Tolerance is essential. It is also the lowest common denominator of virtue. Being the one thing that everyone will agree upon, it can be a great starting point. However, as an ending point it’s inadequate.”

7. “When you’re dealing with the faculty, or… that group that thinks otherwise…” – Anne Reenstierna (head of school at Brimmer & May — MA — 1985-2012)

I heard Anne throw this provocative line out with a wink during a keynote address at another school head’s conference. While her remarks went on to show that she deeply respected and loved her faculty, her point was an important one for me. It reminded me of a dialogue my dad and I had a few times when I was succeeding him as head at Hyde in my early 30s: “You’re doing it again.”… Me: “Doing what?”… Dad: “Thinking like a faculty member.”… Me: “But I am a member of the faculty?”… Dad: “No, you’re the head of school!”

It took a while to sink in, but two messages began to take hold: First, most heads of school do, in fact, start out as faculty members — e.g., all of those quoted in this post logged many years as teachers and coaches prior to being heads of school — before being tossed into a maelstrom where they are responsible for multiple constituencies: e.g., parents, maintenance/dining/secretarial staff, alumni, students, and yes, faculty. So, if the non-faculty constituencies perceive you as either part of or partial to the faculty, you’ve got problems on your hands…. Second, as head of school, you move from being evaluated on how you are doing in your job as a teacher, coach, or administrator to being the only person on the payroll who is evaluated on how it (i.e., the school) is doing. (And unlike everyone else on the payroll, that evaluation is done by the board.) Suffice it to say that the job comes with its lonely moments.

In any case, Anne’s comment hit home because it came at the very time I was internalizing that realization.

8. “Headmasters have powers at their disposal with which Prime Ministers have never yet been invested” – Winston Churchill, 1874-1965

I gather that the young Winston was quite the handful for all of his headmasters.

9. “Well, Malcolm, while I was in my office today I heard a funny sound… and what do you think it was? It was your mother chopping wood. There you see your mother — getting up early; cooking meals all day long; washing and ironing; — and still she has to go out in the back yard and chop wood. I suppose she just got tired of asking you.” — T. Holmes (“Bud”) Moore — New Hampton School (NH) legend with a 70-year tenure, including 33 years as Headmaster and President — by way of Thornton Wilder.

I was maybe 7 or 8, a “fac brat” (my dad started out at New Hampton where he spent 14 years) aimlessly wandering the halls of the admin building when Mr. Moore’s exec assistant stopped me to tell me that he would like a word with me. Being best buddies with his youngest son, I stepped into the headmaster’s office thinking he might give me a lollipop or something. Instead, he proceeded to lay the above sentences on me before taking a phone call in mid-spiel and waving me out the door with a smile. I left his office mystified, but soon forgot about upon exiting the building in search of other amusements. Then, a few nights later I attended the annual faculty play. They were presenting Thornton Wilder’s Our Town for the whole school community. I followed it all as well as any kid my age might, especially zeroing in on the parts played by my parents. And just as I was nodding off, Mr. Moore — as “Dr. Gibbs” — proceeded to recite the very same lines! It was then that I realized that our meeting in his office had simply been a chance for him to practice his lines in front of an audience of one, me. Pretty cool, I thought. Yet another reason why growing up on a boarding school campus was a kid’s paradise.

10. I’ll close with something my dad told me when I began as a head of school:

“Leave your Mansion office. Drive out of the campus gate. Continue on down to Leeman Highway. Turn around. Then drive back through the campus gate and continue driving as though you were visiting for the very first time as a prospective admissions family. Then: Never. Lose. That. View.”

Dad said this to me in 1987 when I first became Hyde’s head of school. I’d pass it along to any new head of any school, or for that matter, a new head of anything. You notice: Why is that dumpster in front of the building instead of behind it?… Wow, that Mansion is beautiful!… That dorm could use a new coat of paint… Look out for the ducks! (That one may be unique to Hyde.)

Onward, Malcolm Gauld