NBOA President and CEO
The 2025-26 school year has not been a light one. And we all know that dis-May, the 100 days of May, or May-hem — all terms I learned from you — was no walk in the park either. On the global front, there are rising prices, another war and, most recently, another dangerous virus outbreak. And yet at your school, I’m sure you see moments of humor and hope every day. That’s why so many of you work in an independent school — it’s where you can make an impact on future leaders and a brighter future for all of us.
Another way to lift your spirits as leader is laughter, which may be especially welcome as we bring this school year to a close. I was recently inspired by a Forbes article, “ No Laughing Matter? How Leaders Can Use Humor To Unite Not Divide” because it provides some great advice from a variety of leadership experts.
It may seem risky to use humor in a leadership position. I know what sounds funny in my head can very often not be funny to others. Get it wrong, and you look out of touch, or even worse, cause unnecessary offense or discomfort in the workplace. I agree with the article’s premise, however, that humor can be used with care to connect people in meaningful ways, especially when colleagues are under stress or overwhelmed. I take my work seriously but try not to take myself too seriously, and I know many of you feel the same.
Author Sally Percy presents five tips, but I’d like to focus on three that seem the most relevant to independent school business leaders.
1. Prioritize Alignment, Not Entertainment.
The article’s first point is that humor should serve your message, not compete with it. In a budget presentation, for example, a well-placed analogy or light comment can help make complex information more accessible and memorable. But it should reinforce the point, not distract from it.
2. Avoid Jokes That Rely on Stereotypes.
If someone in these categories hears a joke based on a related stereotype, they may be more likely to hide that aspect of identity and feel uncomfortable at work, which runs counter to the work at your school.
Humor should create inclusion, not division. Avoiding stereotypes whether using humor or not is a given, but humor more than other types of discourse may back us into these kinds of assumptions — we should be vigilant. The article explains that drawing on stereotypes of “‘invisible’ dimensions of diversity, such as sexual orientation, marital situations, neurodiversity and socioeconomic backgrounds” can be “particularly toxic.” If someone in these categories hears a joke based on a related stereotype, they may be more likely to hide that aspect of identity and feel uncomfortable at work, which runs counter to the work at your school.
3. Make Yourself the Target of the Joke
This isn’t being weak but rather showing humility and revealing your human side. Vulnerability builds psychological safety, said one expert quoted in the article. Self-deprecating humor is a way to connect with others because no one is perfect, and when you acknowledge that in a humorous way it invites others in and “humanizes” your leadership position.
It’s imperative to read the room and consider context. A budget meeting for department heads will have a different tone than a financial aid meeting for inquiring parents, for example.
It goes without saying that making jokes at the expense of those lower in the organizational chart as well as customers — in this case students and families — is never a good idea. Acknowledging the absurdity of systematic challenges, however, can help bring people together, said another expert quoted in the piece.
And whenever using humor in the workplace, it’s imperative to read the room and consider context. A budget meeting for department heads will have a different tone than a financial aid meeting for inquiring parents, for example. A little lightness at the top of some gatherings can be effective, but again, it’s important to keep it aligned with your main objectives for the meeting.
In independent schools, where our work is so deeply rooted in mission and community, this balance is especially important. The issues we tackle are serious, and they deserve thoughtful, disciplined leadership. At the same time, the relationships that sustain our work are built on trust, empathy and shared understanding. Sometimes, a moment of humor can open the door to all three.
So, lighten up! Crack a joke! It may be the medicine both you and your team need at this moment!
Jeffrey Shields, FASAE, CAE
NBOA President and CEO
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