Leadership Lessons: Why Laughing Matters in Leadership

Spring 2019

By Olaf Jorgenson and Duncan Lyon

Experienced school leaders know that humor can be an asset—in relationship-building, as an icebreaker, to provide relief in stressful circumstances, or just to show our human side as leaders. It’s a valuable leadership tool, but do we take humor seriously enough?
To find out, we surveyed heads from across NAIS and the California Association of Independent Schools (CAIS) networks and interviewed 15 independent school leaders, asking them to share anecdotes that illustrate the role humor plays in their work. The insights we gained, in addition to our review of research on humor and leadership, helped us better understand ways that levity can make school leaders more effective—and how laughter shapes healthier school cultures.

The Thing of Humor

The writer Russell Baker notes, “When hoping to bag a piece of humor with your net, nothing seems funny. The thing works the other way around. Humor is funny when it sneaks up on you and takes you by surprise.” We all know this to be true, yet the heads we interviewed use humor in intentional ways. So why and how does the humor “thing” work in independent school leadership?
Research examining humor’s impact in the workplace supports its important role in school leadership as well. “Laughter relieves stress and boredom, boosts engagement and well-being, and spurs not only creativity and collaboration, but also analytic precision and productivity,” states Alison Beard in “Leading with Humor,” a May 2014 Harvard Business Review article. Further, “if you are able to land a joke in a professional setting, your colleagues are more likely to view you as competent and attribute higher status to you,” according to “Humor is Serious Business,” a July 2017 Stanford Business Journal article by Joel Stein.
Humor is also an important de-escalating technique. Daniel Goleman coined the term “amygdala hijack,” referring to the debilitating effects of stress on the rational brain. Laughter can mitigate these effects, says Mike Riera, author, psychologist, and head of school at Brentwood School (CA), citing research that demonstrates the powerful effect of laughter in reducing the stress hormone cortisol. In this way, humor makes us less defensive and hastens our return to equilibrium when we’re upset or off balance.
Humor’s advantages extend on an organizational scale as well. “Research shows cultures that incorporate humor are more resilient,” as reported in “Why Funny Leaders Are Better Leaders,” a February 2018 Inc. Magazine article by Leigh Buchanan. “It’s also helpful in times of stress because laughing releases oxytocin, which facilitates social bonding and increases trust.” These are powerful assets in a healthy organization.
In addition to its favorable influence on individuals and organizational culture, humor is a way to make what you say more memorable. People remember content when it’s funny. Molecular biologist John Medina says in his book Brain Rules that “the brain doesn’t pay attention to boring things.” Medina calls laughter “an emotionally charged event,” releasing dopamine while aiding memory encoding and processing speed.

How to Be Funny (Even if You’re Not)

Research suggests that after age 23, Americans tend to laugh much less and begin to perceive themselves as less funny. To some extent, we all struggle with our “humor IQ.” How can school leaders move the needle on their humor skill set?
First, practice being self-deprecating—which is the opposite of everything you’ve ever done, Stein says. “Self-deprecation humanizes leaders, creates connections with employees, and makes people think the self-deprecating person is even more powerful than she is. After all, if she can afford to mock herself, she must be confident in her abilities. [Such humor] also signals to employees that they are allowed to be funny.” Stein also advises leaders to avoid jokes that are aggressive—roasts, teasing, mocking—and never to punch down by making an employee the butt of your joke. “Instead, punch yourself.”
In The Humor Code: A Global Search for What Makes Things Funny, Joel Warner and Peter McGraw offer recommendations for business executives seeking to raise their humor IQ that are salient for school leaders as well:
  • It’s not whether you’re funny, it’s what kind of funny you are. Be honest and authentic.
  • If you can’t be “ha-ha” funny, at least be “a-ha!” funny. Cleverness is sometimes good enough.
  • Good comedy is a conspiracy. Create an in-group.
  • Don’t be afraid to chuckle at yourself. It signals everything is OK.
  • Laughter is disarming. Poke fun at the stuff everyone’s worried about.

Leading with Laughter in School

In our surveys, several leaders mentioned that humor makes them more accessible and welcoming, which helps with closing the space that the head’s positional authority creates. Other interviewees spoke to the importance of taking oneself down a peg in the eyes of faculty and staff. Mark Shpall, head of de Toledo High School (CA), commented that self-effacement makes authentic relationships possible where they would otherwise not occur because humor has a leveling effect. It is a sort of relationship gateway. For example, he says, “We have a group that does sketch comedy videos for the whole school. They always come up with a sketch that will poke fun at me, which, as long as it is in good taste, I never say no to.”
Humor is a tool that leaders can employ to restore equilibrium and to set the tone when it’s needed, a kind of antidote to the anxiety that lurks within and occasionally pervades in our schools. “When things get too heavy, go light. When things get too light, go heavy,” says Joel Pelcyger, head of Pluralistic School One (CA). Another head noted that “our teams take cues from us. The ‘if she is not worried, then I am not worried’ kind of thinking can sometimes be best instigated by a well-timed joke.”
Numerous heads with whom we spoke described using humor to de-escalate a situation. Ruth Glass, a retired head who served most recently at Lake Tahoe School (CA), shared this story:

One of my favorite lessons in humor came from the inimitable Betty Brown, then head of The Langley School (VA). At the time, I was the middle school head. One morning I had an irate sixth-grade father waiting outside my office. Apparently, the science teacher had approved one of the boys bringing a packaged condom to school to show (still packaged) as part of his presentation on birth control. It would have been helpful had the teacher informed me of such in advance, but that was not the case. Dissatisfied with my apology—and defense of the teacher—the father stormed up to Betty’s office and, shaking with rage, demanded to know if she would like him to show her a condom. Betty, being Betty, kept a straight face and handled the situation perfectly. She confessed to me, however, that what she wanted to reply was, “Not now. I have a headache.”
And suddenly, what had seemed a very big deal to Glass was not really a big deal at all. Instead, it was just funny.

Humor in Action

In our survey, several heads said they use humor intentionally as a device in public speaking, assemblies, and in other public presentations. Zachary Roberts, head of Gateway School (CA), shared that “balancing humor and serious sentiment is a critical recipe for public speaking at celebrations, retirements, and other events. Taking risks to behave in new and unexpected ways brings great situational humor.” On this point, Ilise Faye, head of Hollywood Schoolhouse (CA), described the various ways she deliberately builds opportunities to inject humor into the school year: Comedians host the school auction, the staff conducts “lost and found fashion shows” to return items to students, and the development office creates video parodies of popular songs to increase participation in annual giving. “We went from 75 percent to 100 percent in one week!” she reports.
A few heads admitted to being cautious about using humor, expressing concerns that misplaced jocularity or the wrong kind of joke might well reduce perceptions of an administrator’s competence. “I believe that sarcastic humor creates a superior/inferior relationship,” says Bill Sinfield, head of Sandia Prep (NM). “I’ve learned that it’s far better to laugh at my own foibles and invite others to laugh with me.” Humor, like fire, has a fragility and a power to it. It can be enjoyed and then extinguished quickly or be used proverbially to burn down a building.
When weighing and ultimately approving a prank that involved covering a colleague’s entire office in aluminum foil (see image at left), Melinda Tsapatsaris, head of school at Westland School (CA), illustrated the choices leaders make when it comes to deciding whether a humorous act or antic is appropriate. She knew that the reaction could have gone either way, and she took the chance. The prank went well and helped her to better understand what kind of humor builds workplace culture at her school. Such understanding may well involve mistakes in some school settings, but based on what we heard from heads, the benefits outweigh the risks as long as the leader remains thoughtful, sensitive, and attuned to the audience.

Foiled! In the spirit of humor, an entire office at Westland School was covered in aluminum foil. Courtesy of Westland School
Among the strongest impressions we drew from our exploration of this subject is that it’s ripe for further discovery. Over and over, we heard that humor is an underexplored and widely appreciated dimension of leading students, teachers, parents, and boards. It can be hard to get right, but every head with whom we spoke agreed that the most successful school leaders have an evolved sense of humor—whether by default or practiced design—and that humor is an inextricable trait of a healthy school culture. In the words of Eric Sevareid, “Next to power without honor, the most dangerous thing in the world is power without humor.”
Olaf Jorgenson
Olaf Jorgenson

Olaf Jorgenson is head of school at Almaden Country Day School in San Jose, California.

Duncan Lyon

Duncan Lyon is head of school at The Carey School in San Mateo, California.