Awesome Leadership Lessons from the departures of Bill Simmons & Jon Stewart

When a noted entertainment personality leaves their stage, the world takes note and often takes a deeper look at their accomplishments.

In the first half of 2015, we’ve seen two major personalities announce departures from their lofty perches: Jon Stewart of the Daily Show and Bill Simmons from ESPN.  While they left on very different terms, both leave a legacy of leadership lessons that goes beyond their personal success and branding.  We can all learn from both of them.

{Ed note: Neither Stewart nor Simmons are perfect; we all have faults and both these men have shown qualities worth learning from which we’ll focus on here today.}

Leadership Lessons from Bill Simmons & Jon Stewart

“The growth and development of people is the highest calling of leadership.” — Harvey S. Firestone

While there are many responsibilities of a good leader, both Simmons and Stewart excelled at one particularly crucial area: developing their people.

Leadership Lessons Jon Stewart of the Daily Show

Lesson #1: The greatest role of a leader is to make more leaders.

“The function of leadership is to produce more leaders, not more followers.” — Ralph Nader

Whether you look at the corporate world, at companies like GE, where Jack Welch built a leadership machine in Crotonville, or in the sports world at great coaching trees, like Bill Walsh and Bill Parcells, developing those under you is a powerful tool for a leader.  It’s not a coincidence that coaches with great coaching trees go on to win championships and companies that develop leaders see great success, even when some leave.

What’s fascinating to look at with Jon Stewart is the impressive list of talent he’s helped develop that now has gone on to their own success, which includes names you’ll recognize like:

  • John Oliver went from little-known comic in the UK to now having his own HBO show, “Last Week Tonight.”
  • Stephen Colbert grew into his own show, “the Colbert Report” to now succeeding David Letterman.
  • Larry Wilmore has gone on to develop the sitcom, “Black-ish,” and now his own show, “The Nightly Show with Larry Wilmore.”
  • Steve Carrell has gone onto become a repeatedly, award-nominated actor first on “The Office,” and most recently for his work in the movie, “Foxcatcher.”

A leader does not find, attract, and develop this kind of talent by accident. And thanks to this article about how Stewart helped Oliver, we know Stewart really cared:

“Oliver was concerned that something tragic might happen during the summer of 2013 [when Stewart was on hiatus directing Rosewater] and viewers would want Stewart’s particular comedic approach to help them cope. Oliver worried that he would not have what it takes to satisfy the audience. To which Stewart replied that should such a moment occur, it would be up to Oliver to prove that he had what it takes to deliver what the audience needed.”

Showing confidence in your people to rise to the occasion and setting a great example, is what a great leader should do and what Stewart had done with that statement; he trusted Oliver could handle it, and knew that Oliver had seen how he handled things in the past. Stewart didn’t dictate specifically what to do so Oliver could find his own way.

Being a leader means trusting your people and helping them grow to become more than they are when they joined you. You can see how much Stewart was loved by Colbert’s off script thank you on behalf of so many people Stewart helped:

Leadership Lessons Bill Simmons, formerly of ESPN

Lesson #2: Leaders develop people, not clones.

“…Never promote a man who does things the way you, the boss do it…The greatest praise for a man is, “I don’t understand how he does it and couldn’t do it this way myself; but he gets splendid results.” This is a man who is doing his own work.” – Peter Drucker

A common mistake first-time leaders make is confusing making clones with developing leaders. You don’t want a room full of people who do everything exactly as you do; that just gives you “Yes Men” who can’t think or innovate on their own. Instead, you want to instill a set of values and a standard for work that everyone follows while they develop their own way of doing things.

When Bill Simmons’s career took off it was because his down-to-earth, I’m-a-fan-just-like-you writing style resonated. And when he got the chance to expand from just his writing to his own ESPN-owned site, Grantland, it was easy to expect to just be full of Simmons-style content and writing. But instead, as Jeb Lund of Rolling Stone writes, Simmons took a different approach and gave people a chance to flourish on their own:

“Instead of paying people for the resumes they already had, Grantland has done an admirable job of paying to create resumes many writers would like to have.”

And it wasn’t just Lund’s 3rd-party observation. The proof is in Simmons’s staff. As his departure surprised many sports fans, I noticed one of the many talented writers he hired to work on Grantland, Bill Barnwell, tweeted the following that echoes this:

Imagine the honor of having someone feel that way about how you helped their career. I find it to be one of the most rewarding feelings of being a leader.

Love or hate Simmons’s writing, it’s clear he has done something special to allow quite a few great writers to develop and find their voice via his site, Grantland.

“If you want to go fast, go alone. If you want to go far, go together.” – African Proverb

Simmons and Stewart show that when you go together, you can accomplish great things if you work to develop your people and help them find their unique way to deliver great results.  I’ve seen this firsthand and it’s amazing what people can do when you connect your mission with their personal growth.  Do you do this for your people?

Leadership Lessons Bill Simmons and Jon Stewart