September 19, 2025
BUSINESS

Zelle’s Denise Leonhard says a lack of humor at work ‘kills creativity’



Good morning. When Zelle chief Denise Leonhard interviewed Preston McCaskill to head up operations of the peer-to-peer payment platform last year, she was impressed by his preparation, problem-solving instincts and curiosity. But what cemented the deal for her was his sense of humor.  She “cracked a couple of jokes and gave him the space to be able to crack a few jokes,” she says. Once they started laughing, she knew he’d fit well with the team.

These are challenging times to be funny. Jokes can offend, annoy, insult or fall flat. Diverse teams mean diverse senses of humor and social media isn’t kind to jokes that are tasteless or taken out of context.

Yet numerous studies show that Leonard is right to believe humor promotes creativity, productivity, connections, and culture. “If you actually have humor in the room, people will be willing to put in the extra hours to get something done because they’re enjoying themselves,” she said when we met yesterday. A lack of humor, on the other hand, “kills creativity and makes people want to work less.” But how can leaders deploy humor without doing damage?

Make the joke about you—Self-deprecating humor can be a potent tool for any leader. Done well, it humanizes you and can make you more relatable. Avoid sharing stories that might make colleagues question your intelligence, ethics or ability to do the job. Family is fair game if your partner and kids come off well but jokes about your Gulfstream or billionaire retreat might fall flat.

Ease tension—Former Cisco CEO John Chambers twice showed me the different duck calls he’d use to break up tension and remind people to relax: once as a demonstration and the second time in a meeting that needed it. As Zelle’s Leonard says, that kind of move “takes a lot of the pressure out of the room, and it also gets people to feel more comfortable.”

Foster a sense of fun—Richard Branson understands the power of a crazy costume in generating buzz and making Virgin Group look like a great place to work. Better yet, he’s especially willing to look silly for a good cause, like the time he dressed as a flight attendant for the Starlight Foundation after losing a bet to Air Asia’s Tony Fernandez. Leonard joined PayPal in 2015 as it was spinning out of eBay and “was like a gangly teenager that had all this opportunity but didn’t know what to do with it.” She credits former CEO Dan Schulman with inspiring a culture of fun and shared mission that started with treating people well.

Contact CEO Daily via Diane Brady at diane.brady@fortune.com

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The markets

S&P 500 futures were flat this morning. The index closed up 0.48% in its last session, hitting a new all-time high at 6,631.96. STOXX Europe 600 was up 0.3% in early trading. The U.K.’s FTSE 100 was flat in early trading. Japan’s Nikkei 225 was down 0.57%. China’s CSI 300 was flat. The South Korea KOSPI was down 0.46%. India’s Nifty 50 was down 0.37% before the end of the session. Bitcoin fell to $117K.

Around the watercooler

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Jimmy Kimmel’s canned show will be replaced by a Charlie Kirk tribute — and an angry ABC affiliate is demanding a donation to Turning Point USA by Nino Paoli

CEO Daily is compiled and edited by Joey Abrams and Jim Edwards.

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