Humor and Leadership: How Leaders Use Levity and Laughter to Build High-Performance Workplace Cultures
Leading With Laughter
The former CEO and founder of Spanx, Sara Blakely, regularly highlighted her mistakes during their company-wide “Oops Meetings.” She shared her oops through humor-filled stories, always culminating with her dancing to a song that was evocative of the mistake she’d made, while inviting employees to dance and cheer her on for owning her mistake. Her actions, through her stories, dancing, and especially her self-effacing wit, demonstrated that it’s okay to be vulnerable, make mistakes if you own up to them and learn from them, and have a bit of silly fun.
The CEO of Beryl, Paul Spiegelman (seen below donning a funny wig for one of his employee video updates), a self-described introvert, uses humor in his video updates to employees, and once made an appearance on the call center floor at midnight dressed as a matador on rollerblades to check in with the night shift.
Or consider how one big banana donned a big banana costume for the sake of charity.
As part of their annual charity fundraising efforts, a branch within a Canadian federal government department runs a “Dress Your Boss” event. Employees pay to vote for different managers to wear different costumes all day at work on Halloween.
Shelley Borys, the Director General of the branch, was voted into wearing, yes, a banana costume for the entire day. Not only did she willingly don the ridiculous outfit, she upped the ante and raised even more money for the charity by offering to wear the banana costume to her meeting with the even bigger Big Banana if five more employees made a donation. Naturally, the employees quickly ponied up and there is now a photo displayed in the office commemorating her banana-wearing visit with the President.
In other dares, Borys has accepted bets to raise money for their charity that resulted in her singing in front of the executive committee (she is quick to point out, she is not a singer) and breaking out a saxophone for the first time in 30 years to perform The Pink Panther theme song in front of employees at a summer event. Yes, Borys clearly knows how to turn fundraisers into fun raisers!
These examples, while perhaps still relatively rare, aren’t as unusual as you might believe. In my research of inspiring workplaces around the world, one characteristic always stood out. Many of the most effective leaders, teams, and organizations embraced a spirit of fun. Although we all sometimes bring some humor to work accidentally, these leaders intentionally use levity to drive results!
The above excerpt is from the chapter “Leading With Laughter” in my latest book, “Small Moments, Big Outcomes: How Leaders Create Cultures That Fuel Extraordinary Results.”
And for some principles on how to lead effectively with humour without getting fired, check out my blog, Managing to Have Fun
And, as always, let me know what you think? Have you had a boss whose sense of humor you appreciated? Or, perhaps you worked with a boss whose sense of humor you DIDN’T appreciate!?
Please leave a comment, question, or tip below!
Known as “The Workplace Energizer!” Michael Kerr is a Canadian Hall of Fame keynote speaker on workplace culture, workplace culture leadership, and humor in the workplace. Michael Kerr is the author of nine books, including Small Moments, Big Outcomes: How Leaders Create Cultures That Fuel Extraordinary Results. Michael is known as one of the most entertaining, humorous, and insightful keynote speakers on workplace culture and leadership in Canada.
“By far, Michael Kerr was the best speaker we ever had.” Rod Smith, VP Business Development, Century Vallen




