A Headmaster's Daughter

Becca Hamm Conard | January 15th, 2023

I woke up to my phone ringing. It was 4am and the caller ID said ‘Marcus.’ Looking outside I saw clear skies, and listening carefully I heard movement down the hallway. Bracing myself for the conversation, I flipped my phone open and said without introduction, “He’s checking the weather now, but it doesn’t look good, there’s no snow here.” Not for the first time Marcus complained, “It’s because he’s from Vermont, isn’t it? The old headmaster was from the south, we got snow days all the time…what if I come spray water on your driveway?” After requesting that Marcus please not actively sabotage my family by icing our driveway and assuring him that I would text as soon as I knew if he should cram for his test or enjoy his snow day, I hung up. There wasn’t much time left before my alarm, and I could hear my dad consulting with the facilities manager on the phone so I might as well stay up to hear if it would be a snow day.
The phone calls between 2am and 4am were just part of the winter experience for a headmaster’s daughter, especially when my friends had tests. While these early morning calls were pretty benign, they constituted another element of my high school experience that was unique to being the child of the head of school. Snow days were easy to navigate, although I did need the moral fortitude to reject bribes. Other situations, however, were distinctly challenging for me and my family.
As the head of school there will be expectations and responsibilities placed on your children that are beyond those of their peers, and your role as a parent will be changed by those expectations. It’s important that you consider and discuss with your family how everyone feels about the way your job will impact their experiences. The situations you and your family navigate will cover a wide spectrum.
In general, heads of school and senior administrators need to maintain separate spheres for school and home. Conversations during dinner at home cannot come up at school. If your child complains about a teacher (unless it is a serious complaint) you cannot bring it up with your colleagues. Likewise if you have an interesting story about a meeting with a colleague, your child cannot share that anecdote with their peers. If this division between home and school can’t be maintained it will become difficult to have open conversations with your children, unburdened conversations with teachers and staff, and it will challenge the relationships between your children and their teachers. There will obviously be times when you and your children have to keep things from one another, and this will become apparent when you have to make the tough decisions that come with the job. Faculty members sometimes have to be let go and, if possible, you should avoid your child being in the class of a teacher on probation so your child is not caught in the middle if the teacher is dismissed.
Normally the lines of communication between teacher, parent and student are clear. There is a degree of trust between students and their teachers that the primary communication is between them, and the teacher will inform the student before they reach out to their parents. This expectation blurs when your parent is the head of school. The teacher may be uncomfortable reaching out to the parent because they may be reporting bad news to their boss about said boss’s child. The reverse is also a possibility. The teacher may be too comfortable reaching out to the parent without the student knowing, damaging the trust between the student and teacher. I’ve experienced both situations as a student and I have to say the latter was extremely frustrating. Some teachers would actually ask my dad to intervene in academic situations that they would never bring up with another parent. My personal favorite was when I was late turning in my edits on an article for the school newspaper and the advisor thought it was appropriate to ask my dad to just do the edits for me. Other teachers clearly felt the pressure of the presence of the headmaster’s daughter. I remember vividly when my college counselor thought I was applying to eight colleges and I told him I only applied to four and none were “safeties.” I could see the panic written all over his face. He was going to be the college counselor who couldn’t get the headmaster’s daughter into college. I did get into college, and he’s a head of school now so it all worked out, but the terror in his eyes was real.
As the head of school or a senior administrator, you need to be direct and absolutely clear with your child’s teachers about the appropriate lines of communication, whether that means they communicate with your partner or how they contact you. They also need to know that if they choose to communicate with you as the parent, you will keep that relationship separate from your professional relationship with them. This includes disciplinary issues. It is not unusual for teenagers to get into some trouble at school. And there are plenty of stories about heads of school whose children engaged in wildly inappropriate behavior. If your child engages in rule-breaking behavior, in a big or small way, it needs to be clear to you, your child, and your child’s teachers that there will be no preferential treatment. When issues arise with your child, if they won’t be handled as they would with any other student–and I say this as a headmaster’s child and as a teacher–then your child should not be at the same school as you. It will undermine your relationship with your staff, and frankly it is uncomfortable as a student to receive that kind of special treatment. Likewise if teachers are giving your child special treatment, that needs to be nipped in the bud. Hopefully your child will be mature enough to not respond to favoritism of any kind, which is a conversation the two of you should have.
Even without preferential treatment it may be difficult for your child to connect with their peers. They may face issues of inclusion and trust, given that they live with the person who is perceived as being the one in charge of rules and discipline. Students like to complain about teachers and administrators, and your child may hear things they don’t particularly enjoy. They are going to need some maturity, a bit of a tough skin, and an understanding of what they’re getting into. Some schools will host gatherings for the head of school’s children to meet a few of their peers, and during those get-togethers I found it the easiest to connect with the children of trustees, faculty and staff, simply because they had an appreciation for what my experience was like. I will say I didn’t readily get invited to parties until I had demonstrated that I wasn’t a narc. And once I was at said parties, it was obviously important that I maintained a sense of decorum and not be in a setting where compromising photos of any kind could be taken. I could also never ever host any gathering at my house where alcohol would be served. The headmaster’s house is (usually) school property so on top of the optical and messaging issues there are massive liability concerns for the school if there is underage drinking.
More difficult is expulsions. When I was in high school one of my classmates was (justifiably) expelled. It was a horrible, unavoidable experience where this classmates’ friends were spreading misinformation that reflected poorly on my father and verbally maligning him in the classroom. The teacher handled the situation poorly, announcing to the class, “I’m not just defending him because his daughter’s in the room.” And I was unable to defend his character without revealing information that I had learned in confidence. I spent a lot of time in the counselors’ offices as the situation played out because it was distressing to be around my classmates. To this day I am grateful for my close friends who supported me, who talked to the boy that called my dad a liar so that he apologized to me, and who stood up for my dad when I wasn’t in a position to do so. It was incredibly hard for me to prioritize the confidentiality that is the responsibility that came with being the headmaster’s child over my desire to defend him, but that’s the job. Choosing to be a head of school is asking your child to shoulder responsibility for your job in addition to their high school experience. You both (and your partner, if you have one) need to be willing to take that on, trust each other, and communicate well.
Being the child of the head of school isn’t solely about responsibility and navigating complex situations though. In hindsight I wouldn’t trade my high school experience for any other. I had incredible friends who helped me navigate all of it and my nuanced relationships with teachers made me a better teacher when I went into the profession. Having parents in education is also an incredible opportunity to have. Most parents and their children exist in different worlds and have to work to bridge that gap, but we all shared the same world (my mother is also in education but at schools I didn’t attend). I understood my parents’ jobs, their day to day lives, their friends and coworkers in a way that other kids simply didn’t. And it went both ways. I genuinely don’t think I ever uttered the classic teenage mantra, “you just don’t understand!” to my parents because they absolutely did understand. They knew how stressful high school was, they knew what the social dynamics were like, they understood what was important to me and what wasn’t. We talked about pedagogy at the dinner table, stopped for coffee on our way into school together, and were there for all of each other’s successes. My dad came to my home games (and if he couldn’t be at the field he could see the game from his office) and as the head of school he had to maintain propriety so he was an ideal sideline parent. My mom was a coach at her school so she would work with me after games and practices (and was also a perfect sideline parent). It was a little weird to have my dad be at prom, but when I graduated he was the one to hand me my diploma and give me a hug. It was also funny that then my classmates tried to hug him too, a clear sign of how comfortable we’d all become with the situation. And yes, when it came time for superlatives I won “Most Faculty Pull.”

If you are a head of school candidate and have children of your own or you are already heading a school that your own kids attend, you can find some useful guidance at – Your Own Child(ren) in Your School. Will That Work? – to help you and your family navigate the experience.

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