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Zelle chief Denise Leonhard says a lack of humor at work ‘kills creativity and makes people want to work less’

Diane Brady
By
Diane Brady
Diane Brady
Executive Editorial Director
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Diane Brady
By
Diane Brady
Diane Brady
Executive Editorial Director
Down Arrow Button Icon
September 19, 2025, 5:16 AM ET
Photo: Zelle GM Denise Leonhard
Zelle GM Denise Leonhard.Photo supplied by Zelle
  • In today’s CEO Daily: Diane Brady talks to Zelle chief Denise Leonhard about deploying humor as a leadership skill.
  • The big story: Trump suggests yanking licenses of TV networks that criticize him.
  • The markets: Asia is down but the S&P 500 hit another record peak.
  • Plus: All the news and watercooler chat from Fortune.

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.

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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 Leonhard 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 Leonhard 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. Leonhard 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

Top news

Kimmel firing leads to boycott calls

Social media users are calling for boycotts of ABC parent company Disney after “Jimmy Kimmel Live!” was suspended on Wednesday following the host’s comments on the recent assassination of Charlie Kirk. Critics describe the move as an affront to free speech.

FCC chief favors action against networks

Federal Communications Commission chair Brendan Carr also said that broadcasters face “the possibility of fines or licensed revocation from the FCC” if they run Kimmel’s show. “We can do this the easy way or the hard way. These companies can find ways to change conduct, to take action, frankly, on Kimmel or there is going to be additional work for the FCC ahead,” Carr said, according to a report in the WSJ, which summarizes at length all the ways the Trump Administration wants to suppress its opponents' speech. Not all Republicans are comfortable with the White House controlling what is said on TV.

Trump suggests yanking licenses of TV networks that criticize him

“I have read someplace that the networks were 97% against me," Trump said aboard Air Force One. “They give me wholly bad publicity, press. They're getting a license. I would think maybe their license should be taken away.” 

Trump allies Larry and David Ellison set to become major media owners

The Oracle founder and his son are major stakeholders in CBS and Paramount and are hoping to acquire equity in the companies that own The Free Press, CNN, HBO, Warner Bros., and TikTok. If all goes to plan, it would make the Ellison family more powerful as media moguls than Rupert Murdoch, according to Puck founder and ex-banker William Cohan.

Quote of the Day

“From Comedy Central. It’s the all-new government-approved ‘Daily Show’ with your patriotically obedient host, Jon Stewart!” See the video here.

Deutsche Bank CEO faces $178 million trial in December

A Frankfurt court will hear allegations from a former Deutsche Bank executive that CEO Christian Sewing concealed his approval of complex derivatives trades the bank made to allegedly hide losses at Italian bank Monte dei Paschi. The suit is being brought by one of the executives who was prosecuted and acquitted over the trades, and who now alleges his reputation was damaged by Sewing’s actions at the time. Deutsche Bank denies the allegations and says its own investigation found no wrongdoing.

Elon Musk sleeps at xAI office

Musk spent the summer working intensely on his AI startup, according to the NYT, working such long hours that he occasionally slept overnight at his Palo Alto office.

BofA will raise minimum wage

Bank of America is raising its minimum wage to $25 per hour starting next month, marking a 67% increase since 2017. CEO Brian Moynihan, however, noted in a Bloomberg TV interview on Tuesday that the onset of AI has led to cuts in certain departments.

Activist investor goes after Cracker Barrel CEO

Activist investor Sardar Biglari urged Cracker Barrel shareholders to vote against CEO Julie Masino on Thursday following an earnings miss and a failed $700 million rebrand. Biglari, who serves as the CEO of Steak ‘n Shake, has launched seven other proxy battles at Cracker Barrel in the past.

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

Dogecoin’s first ETF launches after SEC eases pathway for crypto funds to enter public markets by Ben Weiss

Huawei reveals plans for new Ascend AI chips and superclusters, taking the fight to Nvidia by Nicholas Gordon

Mark Zuckerberg blames bad Wi-Fi after the live demo of his new $800 smart glasses goes horribly wrong by Ashley Lutz

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.

This is the web version of CEO Daily, a newsletter of must-read global insights from CEOs and industry leaders. Sign up to get it delivered free to your inbox.
About the Author
Diane Brady
By Diane BradyExecutive Editorial Director
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Diane Brady writes about the issues and leaders impacting the global business landscape. In addition to writing Fortune’s CEO Daily newsletter, she co-hosts the Leadership Next podcast, interviews newsmakers on stage at events worldwide and oversees the Fortune CEO Initiative. She previously worked at Forbes, McKinsey, Bloomberg Businessweek, the Wall Street Journal, and Maclean's. Her book Fraternity was named one of Amazon’s best books of 2012, and she also co-wrote Connecting the Dots with former Cisco CEO John Chambers.

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