Frank Boyden: What makes for singular leaders?

This past holiday weekend I read John McPhee’s The Headmaster, a very short biography of Frank Boyden, who was headmaster of Deerfield Academy, which is now one of the top prep schools in the US.

Founded in 1797, the academy had risen in prominence through the 19th century. Many New England governors and Congress members went there. But by 1900, Deerfield had declined. There were only about 10 students, and the trustees were very near to closing the school.

Frank Boyden became headmaster of Deerfield in 1902, having just graduated from college. He was hoping to hold the job for a few years to save money for law school. The school’s board trustees, who were very near to closing up the school altogether, took a long shot on Boyden, an unknown and unremarkable member of the latest graduating class from Amherst College, about 20 miles from Deerfield. They had previously invited multiple of the more notable members of his graduating class to take the job. All had declined.

Here’s the amazing part: Frank Boyden was headmaster of Deerfield for 64 years, from 1902 to 1966. In that time it went from a purely local institution of about 10 students to a highly-ranked and internationally-known school. Today, there are over 600 students, more than 10% of which are foreign nationals, and the school has an endowment of $600 million.

What did Frank Boyden do? How did he achieve this incredible feat? McPhee’s book is not an analysis —he calls it a “sketch” of Boyden— and so does not offer any hypotheses. But I found this story remarkable. What made Boyden great? How did he turn this institution around? Are there common threads with other people who had held long tenures at great institutions? Fauci’s 20 year tenure at National Institute of Allergy and Infectious Diseases comes to mind.

In the absence of a more careful analysis, I’ll list some of the features of Boyden as described in The Headmaster that I found remarkable:

• Energy. Boyden gets up early, works all day, and goes to sleep late. He sleeps much less than 8 hours, and all the remaining time appears to be “work”. (Boyden died in 1972, at age 92, but I talk about him in the present tense.)
• Emotional intelligence. Boyden can remember many people’s names. He appears to know when he can tell a white lie and get away with it. He can predict boys’ behaviors and personalities very well. He took bets on marginal characters, and was sometimes proved wrong, but often was proved right with incredible success. Tom Ashley is a Deerfield legend: Boyden talked an unsuccessful local boy, Ashley, into coming to Deerfield. Ashley shined, going on to Amherst, returning to Deerfield as a faculty member, and instituting key reforms at the school before being killed in World War I at age 24. These kinds of bets bred fierce loyalty.
• He developed a cult of personality. He earned the respect of his early students by some crazy stunts, like playing baseball with them and completely throwing himself into the sport. In later years, he earned respect by knowing everyone, being everywhere, and having good advice for people. Deerfield started to take off not in small part because influential people thought Boyden was special, and they wanted their children to be near him.
• He bet that sports would be an educational tool. Boyden decided that sports would be a way to educate his male student body and keep their energies in line. Sports in education were considered somewhat gauche in 1902, so Boyden took a bet that paid off.
• He kept doing the same kind of thing for a long time. Educational institutions are generally conservative. Sure, charter schools are everywhere where there is a struggling public education system. But the children of the wealthy and powerful mostly attend the most conservative, long-standing, highly respected institutions, rather than the most new-fangled. By keeping up his style of education, his cult of personality, the sense that Deerfield was doing something long-running and special, Boyden attracted a certain kind of family.
• He was good at fundraising. This one doesn’t seem interesting or unique enough to me to merit further discussion.

There are a lot of pieces to this story I don’t understand. First, I didn’t go to a prep school, so I don’t know what it’s like to have a fierce loyalty to a headmaster, although I have seen similar dynamics among athletes, who come to respect and believe in their coaches in a way I’ve rarely felt about anyone.

Second, I’m not sure what we should use as the counterfactual for any analysis. What other institutions on the brink of failure hired essentially unqualified people who became brilliant leaders?

Finally, I’m not sure if anything I could learn about Frank Boyden would be relevant for the current age. The idea of long-standing leadership at an institution and the cult of personality seems to have died out. Or maybe it is only that, once an institution becomes important enough, it is unwilling to put so much power into the hands of a single person? So while Boyden grew in influence as Deerfield did, his successors could never “own” the whole institution in quite the same way.

I still find something incredibly Romantic about Boyden’s story. Here was a man that, it appears, was uniquely suited to be a prep school headmaster, and he was in exactly the right time, place, and circumstances to make it happen. There was no wandering about: he essentially did one, very big thing in his life.