Superlative Country Day School is looking for a new Head of School. There at the end of the “God-on-a-good-day” list of wished-for traits for its new leader is “sense of humor.” Really? Indeed, Superlative’s earnest search committee is serious about this list of traits, and they’re deadly serious about their new head having a sense of humor. It seems the last few years at SCDS have been high in drama, and woefully low in laughs.

You’ve sized up the job. SCDS is looking for someone who can lead the complete overhaul of its tepid-on-a-good-day academic program, spearhead a 20 million dollar campaign, engender the respect and affection of its taciturn faculty, build a mighty admissions funnel the likes of which has never been seen in Superlative’s history, and lead a raucously fun college admissions evening for the parents of juniors, right now quivering with anxiety just outside the conference-room door.

So what is a serious, earnest candidate to do? With your accomplishments robustly captured on your resume, your impressive writing skills powering your letter of interest in the SCDS headship, and a thoughtful statement of philosophy giving the team a peek at your personal mission as an educator, how the heck do you get across that you have a sense of humor?

An educator’s humor is quite simply her perspective on the whole venture of child development. It’s the knowledge that somewhere in your school, at this very minute, a child has misunderstood something, misnamed something, written or said something utterly charming or hilarious, and that it’s vital to capture these poignant nuggets. Leaders who are able to articulate a broad perspective on learning, and leaven the dispiriting or demoralizing things that happen at our schools and in the world with humor, can help parents through difficult passages, bring joy and laughter into the lives of children and teenagers, and bring energy and hope to the faculty in the darkest day of winter. While it is clearly important for leaders to bring gravitas and wisdom to school and comfort when called to the pastoral dimension of the headship, it’s equally important to bring the profoundly healing effects of laughter into the halls, classrooms and meeting spaces of your school.

To help the serious SCDS search committee know of your perspective and humor, you might ask one of your references to highlight your Back-to-School night speech, or mention your light touch with faculty meetings, your off-the-wall Halloween get-ups, or your writing in the school newsletter. Your statement of philosophy may be able to impart the joy you feel (and share) at your school work, or you might enclose examples of your writing that highlight serious educational issues within a captivating, humorous and memorable story. Perhaps a faculty member will attest to your ability to leaven a grumpy room of tired teachers during report-writing time.

Don’t be afraid to share your humor in the interview setting. Whether it’s a touch of self-deprecation when you share the event/class/faculty meeting that went awry, or the tale of your first campaign “ask” that threw you off your paces, some effort to show your in-the-moment resilience or quick wit will indirectly show your humor. If you have followed the first rule of improvisation by being a “both/and” thinker, you will likely be able to impart this in your interview.

Let the search team know that you understand the consequences of parents —or teachers or kids—who are worried sick about things that are quite simply a part of a child’s healthy development, whether social setbacks, academic struggles, or bruises (literal or otherwise) in athletic pursuits. Humor is a balm for these nervous parents, teachers, and kids. Show the search team that you are ready to apply the balm….liberally!