When aspiring heads ask me about the hardest part of headship, I think mostly about deal breakers. I see two of them: if you are not willing or able to be socially assertive, and to work very hard, you cannot be a successful head of school.
You might be an introvert at base, but you must become adept at playing the part of a socially assertive person, someone accustomed to initiating social interactions, being the most visible person in the room, often called on to command it. Most of your interactions will have a very clear agenda, from the daily project of modeling the care and connection that the school professes to stand for, to very specific interactions where your place as the boss, chief steward of donors, or team leader is centered. As the Head of School, you'll maintain multiple categories of relationships: admin team members whose trust you must cultivate, teachers who need you to know their work, trustees and donors to be thanked, prospective trustees to be engaged "in the wild," neighbors who might otherwise think of the school solely as a nuisance, aldermen whose support you'll need in a few years for a building project. All of the events you attend, even greeting people in the morning will come with at least a soft agenda. Your Development Director will produce lists of people for you to visit with and to thank--at grandparents day, the gala, in the city where the conference is being held, at the front gate the morning after the Smiths improve their annual gift. You cannot deputize someone else for these tasks. Nor can you do them on your own schedule, if procrastination has been the way you've titrated your social energy. Your thank you to the Smiths loses a little of its impact every day that drifts by after they've made the gift. Most native introverts who've become viable candidates for headships have already made some of this adjustment, but it will require exponentially more psychic energy in the first years of headship. If it's any consolation, not all extroverts are naturals. Those who are egotists at heart or whose social energy is performative are even more likely to struggle, and to fail in explosive ways.
Secondly, you'll work a lot. There is a bottomless list of stuff to be done, activities to be attended, relationships to be stewarded, and you'll be expected to lead all of it, not personally in every instance, but the buck will stop with you. You'll run a Sunday night triage on the week ahead that will often be laughable by 9:00 Monday morning, and by the next Sunday it will tally up to something like 60+ hours. Which means that someone else in your life is going to have to pick up the slack. It's also true that you'll be the only person (well, maybe your partner) keeping track, and the only person who'll really be looking out for your over all well-being. You might be fortunate enough to get a little engagement in "executive leadership sustainability" from the board, but you've also agreed to a compensation package that some will see as an open ticket for more expectations. Time and again people will thank you for coming to the concert or the away game, even comment on how it must be so hard to attend so many things, but most of those same people would be quick to judge you for not being there. You'll have to become artful at proactively managing these expectations and occasionally taking your lumps. Yep, so sad I missed it, looking forward to the home game next Thursday. And by the very nature of your position, you are in a tractor beam bullseye of the highest hopes and dreams families have for their children, and even though their rational brain tells them it's unreasonable, it kind of feels like you, the Head of School, are personally responsible for delivering on all them. A good friend going into his 20th year of headship told me that this last, more than the events and initiatives and task forces, is what weighs on him the most.
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