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.
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.
