This past February, when Jon Stewart announced his impending retirement from Comedy Central’s The Daily Show after sixteen years, the collective mourning began almost immediately. “I have this irrational feeling of sadness, bordering on hurt,” a commentator for Entertainment Weekly said. “I feel wounded. It’s not like a romantic break-up, per se—more like a childhood best friend announcing his family is moving away right before sixth-grade starts.”
“Sixth grade” referring to, of course, the upcoming Presidential election. How would the nation possibly cope without Stewart around to skewer the candidates? “Jon Stewart, we need you in 2016,” pleaded a headline in the New Yorker. His departure, said the magazine, killed the “last hope for bringing some rationality to the 2016 Presidential field.” Stewart’s opponents on the right disagreed, with Fox News’ Megyn Kelly proclaiming, “I don’t think overall he’s been a force for good.”
But a proper assessment of Stewart’s legacy shouldn’t just focus on politics. It should also take into account the business of entertainment, and more specifically, talent generation. In this area, Stewart most certainly has been a force for good. I’ve spent the last ten years studying individuals who are unusually good at helping others build careers and make contributions to their fields. It all started when I discovered a striking pattern: If you take the top fifty most prominent or influential people in many industries, just one or a few top people mentored a disproportionate share of that talent.
Wondering about the secrets of these “superbosses,” I set out to methodically study them. Sifting through mountains of interview transcripts and secondary materials, I identified dozens of superbosses in a wide array of industries, including Alice Waters in food, Oprah Winfrey in television, Michael Miles in consumer packaged goods, Ralph Lauren in fashion, and Bill Walsh in football. Although their personalities varied, these bosses all demonstrated an unusual, even legendary ability to develop the best talent in their industries.
My research turned up two clear superbosses in the field of comedy. The first:Saturday Night Live creator Lorne Michaels. His protégés—Bill Murray, Gilda Radner, John Belushi, Mike Myers, Chris Rock, Amy Poehler, Tina Fey, Seth Meyers, and Jimmy Fallon, to name a few—comprise a Who’s Who of comedy superstars. As my research continued, I realized that another superboss had come onto the scene: Jon Stewart. In a very short time, The Daily Show had discovered and launched a surprising number of comedy stars, including Steve Carell, Stephen Colbert, John Oliver, Ed Helms, and Rob Corddry.
What was Stewart’s secret? Superbosses are exceptionally adept at developing talent because they share particular character traits and adopt a set of common practices that, taken together, are both rare and extraordinarily effective. They are unusually intense and passionate—eating, sleeping, and breathing their businesses and inspiring others to do the same. They create impossibly high work standards that push protégés to their limits. They are geniuses at motivation, inspiring people to do more than they ever thought possible. Remarkably, they can be intimately involved in the detailed work their people are doing, while at the same time lavish responsibility on inexperienced protégés, taking risks with them that seem foolish to outsiders. They encourage the creation of strong, emotional bonds and loyalties between protégés as well as between protégés and themselves.
Stewart embraced most of these tendencies. The work on The Daily Show was fast-paced, with deadlines to be met every day for the night’s show. Stewart expected new performers to step up to the challenge from their very first day. Correspondent Jessica Williams remembered being overwhelmed after receiving the “grand tour” on her first day, and “the next morning, Jon’s like, ‘Okay, so are you ready to be on tonight?’ And I was like, ‘Huh?’” Al Madrigal recalled The Daily Show as “a difficult gig. There’s nothing like it, and the only way to get good at it is to go out there and do it.”
Yet such intense pressure didn’t cause performers to turn on one another. Instead, they pulled together as a group, helping and teaching one another. John Oliversays he learned by checking out unedited interviews performed by Stephen Colbert to “watch how he handled situations. I could see him and his mind working out how things were going to go.” Comments by other cast members reflect the strong loyalties such collaborative effort created. “I kind of owe everything to The Daily Show,” Steve Carell has said, “and I still think of it as…a home… I’ve never been around a group of funnier, smarter people in my life.”
Stewart’s employees are clear about their emotional attachment to him. After Stewart was accused in 2010 of creating a “boy’s club” in an article published in Jezebel, 30 female staffers leapt to his defense in an open letter published on “The Daily Show” website, describing their boss as “generous, humble, genuine, fair, supportive, exacting, stubborn, goofy, hands-on, driven, occasionally infuriating, ethical, down-to-earth”—descriptors that could apply to many of the superbosses I studied. And the affection went both ways. “I love the people here,” Stewart saidwhen he announced his departure. “They’re the best. They’re creative and collaborative and kind.”
Many of us aim for financial or professional success. Stewart achieved both by helping others to build their careers and realize their full potential. He unleashed a generation of humorists to entertain, amuse, and infuriate us. What we’ll ultimately miss most about Stewart thus may not ultimately be his take on current events. It’s his take on talent. Wherever you stand on the political spectrum, his legacy as comedy’s reigning godfather is worth celebrating.
Sydney Finkelstein is the Steven Roth Professor of Management in Dartmouth’s Tuck School of Business and the author of Superbosses: How Exceptional Leaders Manage the Flow of Talent (Portfolio/Penguin, February 2016) from which this article was adapted.
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