"A Headmaster’s Field Guide" Selections

For twenty-four years, I practiced the Headmaster’s profession. Like navigation, basketball, fly-fishing, playing the piano and identifying wild species, only practice truly educates. To understand what the music demands - and your potential and limitation to achieve it - you must move your own fingers on the keys.

After I’d been on the job for nearly two decades, a sympathetic parent said, “I guess you’ve seen it all now.” “Well,” I replied, “it may not happen every day but, truth be told, not one week goes by when I don’t encounter something - and usually many somethings - I’ve never seen and never imagined.” I often longed for a wider horizon and a better ability to anticipate deeper implications.

After a while some events did fall into recognizable patterns. Though the infinite coastline of school life is frequently foggy, one develops a sense that at least you hold a lead line, the outlines of a chart and can discern the next buoy without running aground. Lord knows a fair amount of what lies ahead will be uncharted, but neither is the future completely obscured. Over time, I developed my own lexicon of aphorisms and reminders to which I held fast. They are nowhere near as unerring as a polestar but they provided, from time to time, a certain steadying familiarity. I encourage all heads to build their own list. Perhaps just repeating them when something unanticipated arrived was my own silent invocation, a distant light in the sea of uncertainty.  


One of the great privileges of the work is the enormous opportunity to be kind because there are so many ways a School Head touches other lives. The Head can express care and understanding in ways that set the tone of the school. It is neither arrogance nor I hope vanity to recognize the importance of the job’s singular ability to offer care.


I once heard a famous concert pianist comment that before he played the first note of a composition, he had to hear the last one because the piece “had to tell a story.” Little about beginnings in schools tells a story nor predicts the ending. First steps are often tentative but to move a school forward, taking them is crucial. One of our trustees wisely commented “you don’t have to know your final destination to take a step in the right direction” and I kept that in mind.

Achieving a vision was something akin to what Edison is purported to have said about genius - “2% inspiration and 98% perspiration.” Visions of the future - programs to be put in place, buildings to be built, goals like reputation and financial stability to be achieved - didn’t take very long to imagine. Putting them in place sometimes took decades.


Formal education remains fundamentally paradoxical: it aims to promote high and necessary standards of scholarship, discipline and skill and, simultaneously, to develop individual kids.

One of the great advantages of an independent school is the ability to recognize the eternal reality of the paradox without shackling itself to a formula for resolving it. Standards are important. Individuals are important. If a teacher helps a young person find out what “doing your best” actually means, and that doing your best is actually possible, real progress can result.


Adult development as much as students’ is at the heart of much we hoped for in school. Adults can - and do - develop but how and why this may occur I found increasingly mystifying. Many faculty got better and better.  And some did not. I just decided to deal with some as fixed rather than malleable beings and found that more helpful to us both.

I also came to hope we could develop a mission for faculty that was as intentional as the mission we hoped we were aiming for with the students and that respected the stages and complexity of adult life in some detail.

Two Sides [or more}

As much as it is a cliché, constantly recognizing that pretty much every story had two - and often many - sides sometimes prevented a desire to shoot from the hip.

My favorite color is not gray but an awful lot of situations in school define the term. One learns that finding a way through gray offers a not particularly rewarding and sometimes a downright unsatisfying choice. Dramatic action is usually left to the stage but frequently not to actual life.


Many texts on leadership assert that delegation is “the” key to effective administration. Unquestionably true. But only up to a point. One delegates action and expects results but one never evades responsibility. There is a line between asserting control and expressing confidence. An effective head, I concluded, is willing to tread along it. Or tromp along it.

All A is B but Not All B is A

“Follow your dreams” “Find your passion” “Never give up” I hoped always to find the right way to elevate its converse to equally inspirational status….so the moment a dream was dashed, a passion thwarted, the end of the trail reached the real import of the advice would assert itself. Dreams and determination are often less about specific achievement and more about the spirit of what one could, in real terms, accomplish or feel. Sometimes kids were better at understanding this than their parents.


The budget stands as the most profound expression of our values and our mission. And, for the Head, school finances asserted a constant and unremitting demand.

Independent school per-student costs range from below $3,000 a year to more than $100,000. Norms but no universal standards exist. A School Head remains at the mercy of any number of assertions about leadership, management, vision and fund-raising prowess.

A good Board with reasoned - and reasonable - expectations and committed leadership is essential. It has been noted in many places that a healthy relationship between the Board Chair and the Head of School is essential. My experience was simple. It is.

Successfully navigating the waters of hope and informed understanding of one’s constituency, history and potential requires the Head and the Board to share common observations and mutual goals. And that agreement - or its absence - may determine a Head’s tenure


Simple physical presence in school has no substitute.  I should have kept this on a card in my pocket.


The Head’s day can be a cacophonous procession of issues and personalities without the slightest connection. Tears, laughter, contemplation, speculation, planning, decisive steps, minute detail. Some days are a struggle to keep one’s center in a sea of gaudy intensity - like trying to meditate in Times Square. It is not particularly “lonely” in the Head’s office but the need to attend equitably to wildly different demands belongs only to the Head of School. Going out alone for a walk - or a run - must be as important in the day as answering emails. That was an easy assertion but sometimes it was hard to do.


I have no idea whether or not a quarter century of head mastering accumulates to anything other than a rueful recognition of one’s limits. I came away from the experience feeling it’s an awfully hard job and a truly fascinating one. Over the years, the people who thought I did it well and the ones who thought less of it both expressed themselves. Perhaps my conclusion was they were both right. As I said earlier, every story has two sides.

About The Author

Jay Stroud

Jay Stroud holds degrees from Carleton College, Dartmouth and Columbia where he was a Klingenstein Fellow 1981 – 1982. He began his teaching career in 1967 at the Marvelwood School when it was in Cornwall, Connecticut. In 1971, he joined the faculty at Holderness where he served variously as English teacher, cross country coach, drama director, dorm parent, Director of Studies, Dean of the Faculty and Assistant Headmaster. In the summers from 1983 – 1986, he was a site Director for the Johns Hopkins CTY Program. In 1988 he went to Tabor Academy where he served as Headmaster for 24 years. During that time, he also served on the NEASC Commission on Independent Schools and was a member of the Board of Trustees for a dozen years, chairing the Board in his last year. He retired from Tabor in 2012 and in the spring of 2016 became the Director of the NEASC Commission on Independent Schools. He lives in Quechee, Vermont, with his wife, Leslie, and their son, Ben.