How important is the Head of School?

I am curious to hear from experienced BS parents – how much does the HOS actually influence the school? As DD and I are exploring for her applications for next year, we are seeing a real mixed bag. Any thoughts on how much the culture depends on the HOS? Would you ever send your DK to a school where you simply did not like the HOS?

I think it matters a lot. It set tone/direction/leadership. At my kids’ school, there was a big difference in the environment in my and their opinions under different leadership.

I think it makes a huge difference.

I see how big an influence a great head who’s been there a long time – Millbrook – can have. Drew Castertano’s vision has seeped into every nook and cranny of the school, all the teachers and administrators share that vision, and all the pieces work well together. His successor, I believe, will move the school to new heights. The transition was thoughtful and deliberate, and they have a great guy.

Conversely, a bad head is awful. Hotchkiss had one, who lasted 2 years. On the one hand, these schools are like battleships, hard to change course quickly, but on the other, each Head leaves his/her mark. In the past, Hotchkiss went through a few heads – 3 in ten years? – and each’s vision was different so the school didn’t have all it’s pieces working together in harmony. Luckily, IMHO the current head has set a great course and is pulling the pieces together.

Anyway, all too long winded; the short answer is yes, I do think it is very important.

I agree the HOS matters a lot in setting the culture and tone of the school. Both of my kids attended a PreK - 8th grade school, and we experienced a change of leadership halfway through. By the time my kids were in 8th and 6th grades, we were done supporting the school. My older son graduated 8th grade, and we pulled my younger one out and sent him to public school for 7th and 8th grade. That new head has since been ousted after damaging the schools reputation, and spending insane amounts of money the school didn’t have to spend.

My boys will be attending two different private schools next year, and I feel good about both HOS. While the schools are quite different and one has significantly more financial strength than the other, I do feel confident in the leadership of both heads. I would have serious reservations about sending my child to a school whose HOS did not impress me, or align with my values.

Totally agree with the posters above. My perspective is that of a parent as well as a former BS faculty member. (And @cinnamon1212: FWIW, I don’t know any moms who didn’t have at least a little crush on Drew Casertano. LOL )

Some other particularly impressive Heads of School in recent years: Tad Roach at St. Andrews, Peter Becker at The Gunnery, and Charlie Cahn at Suffield Academy. Ann Pollina, who was HOS when my daughter chose to attend Westover, was a remarkable woman. She retired in the spring of 2015 as she was battling cancer, and the community was devastated when she passed away.

There was one HOS we met during our school visits who we found exceptionally underwhelming. Many things about the school were top-notch, but there’s no way we would consider it after having had even a brief conversation with that person.

The HOS is the largest impact on a school. It is the most important and guiding driver of how everything functions at the school during those years.

Which of the so-called top boarding schools have the best heads of school, and which the worst? Of course, it’s hard to tell with a brand new HOS (like at Andover), and the interim ones are not intended as long-term solutions.

Single. Most. Important. Factor. We chose schools based on the HOS. Right now with Covid, it is even more important. Try to ensure their goals and educational philosophy aligns with your child and family.

MODERATOR’S NOTE: A valid question. But one that should be asked in a new thread and not hijack this one. Hijacking is considered rude to the original poster.

Point taken. My apologies. I’m pretty new here, so please excuse my rudeness. It was unintended. Thank you for pointing it out. Can it be deleted?

HOS played a big part in our school choice and he has handled the COVID crisis exactly as I envisioned he would (actually way beyond what I could envision).

One of the schools that stood out most to us when touring was the one in which the HOS met us after our daughter’s interview. It was really nice making that connection with her and it definitely reinforced the fact that the HOS would be a prominent role in the student’s daily life. Of course, it was a smaller school, so its easier for the HOS to be out and about talking to students and meeting parents, but it definitely left us with a good vibe. Likewise, we met, and loved the HOS of the school where our daughter will be going next year. Of the other 6 schools we toured, we had no idea who the HOS was (though it was/would have been part of the discussion when DD was choosing her school). When I was at BS, we had a phenomenal head for the first 3 years and a sub-par head my senior year. I can’t even remember his name. I agree that a great HOS really sets the stage for a positive learning experience and a cohesive community.

This is a tricky one to me. At a very basic level, no school should hire a head who can’t promote its values and advance its goals. So if a HOS is saying things that just seem off to you, it may be that the school has the wrong values for you. And while I strongly believe that leadership sets the tone, I’d be wary of any school that had became dependent on its head to maintain that tone. You and your kid are going to have little interaction with the head compared to tons of other adults at the school.

Otoh, when a school hires a head, it may have have different priorities than a parent and these may not translate into the same things you are looking at/for. For most parents, you will see the head at public functions (from revisits to sporting events). If you are well-off, you may see them with advancement officers. And if your kid gets into a particularly complicated mess, you may get to know them. But for most of us, we are rating them as public speakers and chit-chatters.

As in all things, I think it depends. I’d think carefully about what you liked or did not and try to sort through that.

I think it is more than public speaking and small talk. As @cinnamon12 mentioned above, it has to do with their vision and values and how that has been embraced by faculty and administrators; how it has “seeped into” all parts of the school and how it is run.

Different HOS have different personalities, too. I remember that when we visited Millbrook, my D was blown away by how the Head knew a lot of details about every single kid (we had met him as we were leaving the Admissions office, and he invited us to walk across campus with him, introducing us to kids along the way). This was in mid-September. He told us that he had a self-imposed deadline for being able to greet each new freshman by name and know a bit about their background and interests by the end of every September. Not all HOS will seek to have such a personal connection to the kids, especially at a very large school, and I suppose for some kids looking at schools, it won’t matter. It did make a difference to us, and while she didn’t enroll at Millbrook, my kid was very impressed ( as was I).

Pieter Mulder, the HOS at Berkshire, also makes a point of actually knowing every student there.

Yes, the spring of my Millbrook son’s sophomore year, Drew Casertano told me he could tell my son really wanted to make the Varsity soccer team because Drew saw him every afternoon, practicing with the school’s best striker. I am certain this would not have been noticed at a bigger school. And Drew was right, soccer was very important to my son. I think it is impressive the head of school knew this about my son. And reflects Drew’s vision that every student be known, and appreciated for who they are.

I agree with @doschicos that the Head’s role is much more than speeches and small talk. Malcolm McKenzie, at Hotchkiss, had a very strong international vision, so that he actively recruited kids from places like Afghanistan, the Palestinian Territories etc as well as creating a senior administrative position for International studies, among other things. He left, and subsequent heads, while of course having a global perspective, have not emphasized the international aspect as much. So that senior administrative position has lapsed, there are no students from more unusual countries etc. So he influenced the direction of the school, but since he was only there for something like ? six years or so, that vision is not something that permeates the school, and the focus has shifted away.

I don’t know about boarding schools specifically, but for private schools generally the values of the HOS may not matter much if he or she prefers to defer to others in the organization. If the HOS lacks energy or a strong personality, or if he/she delegates key personnel and/or curriculum decisions, others in the organization will attempt to put their stamps on the culture and values, even if they are in opposition to those of the HOS.

OP asked:

Question: How important is the head of school ?

Answer: As important as the board of directors allows / wants.

A Head of School can be a figurehead or can be a catalyst for change or something in-between–but this all really depends upon the Board of Director’s wishes.

And I will add that at some schools, the HOS tend to spend more time in their offices, less out and about on campus and at games and student events. Some seem to have much more of a connection to trustees and donors. I wouldn’t want my kid’s school to have a HOS that Just stops by at major events, gladhands the well-known and well- heeled families and kids and then disappears. They are all responsible to some degree for the trustee and donor relationships. But some seem to be more comfortable with the fundraising and showing off artistic renderings of proposed new buildings, than with having any real connections to students.

And if a school needs to be building its endowment or managing faculty issues, and the HOS isn’t doing that (but is very present on campus), that’s a problem too. Not for parents and students, but for the future of the institution.

To be clear, I didn’t mean that the role is only public speaking and public appearances. But that is the part of the role parents will see.

Based on responses here, trustees should weight parent sentiment toward a head highly.