The Stewart School of Talent Development

I’ve been thinking a lot about what makes a good supervisor lately. While I am not presently in a supervisor role, talk has started about the possibility of me getting an intern, and my role on the NACA Conference Committee allows me to work with other staff members whose work I oversee.

I do a lot of reading about what good supervisors do, how they behave, what opportunities they present to those they work with, and how they recognize their good work. But as I looked up from the books or computer screen over the last few weeks, an example sat in front of me- behind a wooden desk.

Consider this excerpt from a 2011 No Fact Zone interview with Stephen Colbert about a longtime boss (and friend) of his:

I’m very lucky to have him as the guy I learned how to produce and write and run a show like this from. He’s also an inspiration for the dedication he puts into the show every day, holding on to a high standard of distilling the jokes down into satire. […] And he has never dropped it, after 12 years he’s still, every day gives everything. And that’s an inspiration to me, that he can stay so focused after all these years and really seem to enjoy himself.

And I’m also lucky to have him as a friend, because, you know, on days when I am completely wrung out, I can call him and say, How do you keep caring, every day? Because there’s nothing in the news that’s getting me going, there’s nothing happening right now with our scripts. I can’t express, I can’t convey a clear vision for anybody, because it’s always ultimately your responsibility, I can’t inspire. […] He is so supportive. I am so lucky to have [him] call me up on a random day and say ‘I like that thing you did last night, and here’s why. And here’s what else you could do with it,’ or call me up and say ‘Hey, help me out, I’m trying to do something tonight. What do you think I should ask Newt Gingrich? What do you think I should ask Donald Rumsfeld?’ And I’m honored that he would ask that of me. And he’s also just a good, fun guy. I’m lucky to have him as a friend, and as a mentor.

Alternatively, consider the visceral and heartfelt reaction to praise that John Oliver had during his sendoff from the same friend and boss:

The fact of the matter is, most of our supervisors, and most of us who have the opportunity to impact the lives of protegees, could learn a thing or two from The Daily Show‘s Jon Stewart.

Part of my weekend was dedicated to reading Sylvia Ann Hewlett’s (Forget a Mentor) Find a Sponsor, a long-awaited and oft-recommended read for me. As I read through the descriptions of what constitutes a sponsor (admittedly, while the bare bones of this blog post murmured under the surface), I couldn’t help but see Stewart in so many of these qualifications. Consider this:

“A sponsor is a senior leader…” Stewart has earned this title. The New York Times has lauded his work, both as a host and developer of strong and hilarious talent, noting that “one of the most underrated accomplishments of Mr. Stewart’s tenure […] has been his maintaining a strong voice while also consistently finding and developing talent.” NPR has afforded Stewart similar praise, conceding “his quick wit and biting satire have taken the once-obscure fake-news show and made it an influential voice in American humor and politics.” And it has won over twenty major awards, including several Emmys for Outstanding Writing and Outstanding Comedy Variety Series.

“who, at a minimum believes in me and goes out for a limb on my behalf, advocates for my next promotion, and provides ‘air cover’ so I can take risks…” Stewart has done this several times for his staff, as evidenced by the great heights the alumni of his program have reached. Because of him, and not despite him, alumni such as Steve Carell, Rob Riggle and Ed Helms have found fame in TV and movies, comedians such as Kristen Schaal and Demetri Martin have been able to heighten their respective profiles, and his alum have even expanded into less likely areas of fame such as comedic literature (John Hodgman and Samantha Bee) and Tony Award-winning comedic musical theater (Josh Gad).

The ritual of creating the show, wherein time for writing, revision, ideation and improvisation are tightly structured, paradoxically provided opportunities for growth beyond constraints for many, and that structure has been credited for the success of Colbert and Oliver, among others. He creates space for his correspondents to form their own distinct but congruent personas, ones that they can carry with them to future pursuits.

The additional success of Colbert, Oliver, Carell, and others; combined with the diverse bench he has on his staff that has or does include multicultural talents such as Wyatt Cenac, Jessica Williams, Olivia Munn, and Aasif Mandvi, can be attributed to other measures of success for a sponsor, such as expands my perception of what I can do, promotes my visibility,and provides stretch opportunities. For example, when Stewart tok six weeks off this past summer to direct his first feature, he allowed Oliver to take his seat at the host’s chair. The persona he was able to cultivate during his time as host led to new offers, offers Stewart was delighted to let him accept.

There are countless other qualities that Jon Stewart embodies that I’d like to similarly personify in my leadership roles. He takes his work seriously and identifies his priorities clearly. This idea may have counted him out of the recent race toward Letterman’s briefly vacant chair; according to Forbes, “there’s not much room for political guests in broadcast late night, and its been stated by several members of his team in the past that Stweart isn’t the biggest fan of movie star interviews, which is what most of the job would entail.” With that said, he showed us after 9/11 that he’s not afraid to be vulnerable when something is important to him. He stands up for what he believes in and will speak up about injustice or wrongdoing- just ask Tucker Carlson or Paul Begala.

Selflessly cultivating talent on his staff is, to me, the most admirable and notable element of Stewart’s leadership. So often, the opportunities presented for our coworkers or proteges to take on new and larger challenges is seen as threatening, a betrayal to the time and energy we have put into developing them. This can be common even in other television settings (JTT and Tim Allen’s differing opinions about his leaving the show is a notable example). But Stewart has always been understanding, and even excited, about advancement opportunities for his correspondents:

There was a time where the premier breeding ground for high-level comedic talent was Lorne Michaels’ network powerhouse Saturday Night Live. And while elements of that are true (a post for another time, I promise!), this network workshop appears to be taking the crown. So as you continue to examine your supervisory style, or to contemplate what it will look like when your opportunity comes, consider taking a few times from the king of late night fake news. Your protegees will thank you for it.