The Power of Humor in Leadership

For school leaders, the month of August ushers in a range of feelings, from excitement to full-on anxiety. Opening faculty meetings and the launch of school loom large, and as we try to reclaim the steadier mindset and perspective of summer, humor can help.


In thinking about the role humor plays in effective school leadership, I found myself returning to my high school yearbook and looking up my quote by author Ken Kesey from One Flew Over the Cuckoo’s Nest. “When you lose your laugh, you lose your footing.”


The benefits of humor when leading a community are real: mitigating situational tension; promoting greater unity in the shared joy of the moment; and underscoring the humility inherent in the belief that we can take our work seriously, but not ourselves. 


I recall a stressful moment when I was a finalist in a head of school search and humor seemed the only way to lighten the mood and infuse some perspective. One of the last meetings after a grueling multi-day schedule was an open session with upper school faculty. It was just before the winter holiday, and as exhausted teachers entered the gathering space, the atmosphere became increasingly heavy. Yikes! 


At the request of the search committee chair, I had prepared comments, but looking at those weary faces, I knew they wouldn’t land well. I read aloud the community statement distributed by the search committee listing two pages of characteristics describing the ideal candidate they were seeking as their next head of school. When I finished, I kidded by saying, “I don’t know any human who has all these qualities but if you do, go for it – they’ll be a great next head of school for you!” There were polite smiles and chuckles but mainly there was a shared light moment from which I pivoted to talk about the competing priorities included in search documents when considering actual people, and the need for the community to decide what was most important to them. The tone of the meeting substantially changed. I emerged from that meeting confident I had been my more natural self. Nineteen years of headship at Greenwich Academy followed, including many humorous highlights.


My friend Bob Whelan, Head of School at Greens Farms Academy, has a fantastic sense of humor. He’s that head with the hilarious social media posts that everyone forwards to you (I speak from experience!) I asked Bob how humor informs and strengthens leadership. His response?  “The effective use of humor can lead to a broad range of positive outcomes: reducing organizational stress, offering perspective at key moments, humanizing the leader, and drawing people together.” Agreed!


But what if we’re not someone capable of generating laughs or, at least, we don’t think we are? That’s okay. Self-deprecating humor is one of the best ways leaders can express humility, bringing others into your circle and being more relatable. Consider teaming up with the person that others see as funny, modeling that it’s alright for others to make fun of you. Or find that funny YouTube clip that launches your meeting with a shared laugh and feel the energy shift in the room.


Humor strengthens the relationships that are the fabric of our communities and that increase the reservoir of goodwill, and school leaders can then draw on that reservoir to help navigate the increasingly choppy waters that mirror a more charged political and cultural landscape. I’m not suggesting that school heads crack jokes about the weighty issues at hand, but instead to look for opportunities to generate joy and appropriately deploy humor as any degree of levity can help mitigate elevated levels of emotion in our current environment.


At RG175, we are fortunate to interact with many exceptional school leaders—people of outstanding character—who express bravery, conviction, empathy, compassion, optimism and yes, humor on a daily basis. Their self-awareness and high EQ give them the ability to laugh at themselves and to use humor as a community builder that helps their schools feel more connected, joyful and unified in their work on behalf of young people. 


Here’s to a great school year ahead, full of purpose and punctuated by shared smiles and hearty laughter. Onward!