In the preview episode for Season 2 of the Life Well Led podcast, I asked my son and co-host Grady who his ultimate “name it and claim it” guest would be. After talking about how fun it would be to interview Charles Barkley or Shaquille O’Neal, he ultimately landed on Michael Jordan. 

Grady’s answer sparked some interesting LinkedIn exchanges about how to view Jordan as a leader. So interesting, in fact, that I thought it warranted exploration in a newsletter. So here we go.

Let’s start with what Jordan’s teammates had to say about his leadership. Here are a few noteworthy quotes from The Last Dance:

"He was pushing us all to be better because he wanted to win. And it worked. He made everyone around him play at a higher level." - Bill Wennington

“Let’s not get it wrong. He was an asshole. He was a jerk. But he was a hell of a teammate.” - Will Perdue

“He wanted to win more than anything, and he expected you to want it just as much.” - BJ Armstrong

Next, let’s consider what Jordan himself had to say about his unique approach to leadership. In one of the most powerful moments from the docuseries, Jordan explains:

“Winning has a price. Leadership has a price. So I pulled people along when they didn’t want to be pulled. I challenged people when they didn’t want to be challenged. And I earned that right because my teammates came after me. They didn’t endure all the things that I endured.”

At this point, he starts to get emotional, his voice tightening and his eyes filling up with tears. Then he finishes:

“When people see this, they’re gonna say, ‘Well, he wasn’t really a nice guy. He may have been a tyrant.’ Well, that’s you, because you never won anything. I wanted to win. But I wanted them to win and be a part of that as well.”

I teared up as I re-watched the clip, so I guess that tells you something about how I feel about Jordan’s approach to leadership. I believe there is something good and honorable about challenging your teammates to work harder than they thought they were capable of working to achieve goals they didn’t think they were capable of achieving. It’s an approach that has motivated me and many others. But for every person such an approach inspires, there’s probably another person it’s going to repel.  

I’m curious where you land on this one:

1. Do you believe Jordan was a great leader?

2. Why or why not?

Season 2, Episode 1 of Life Well Led

In case you missed it last week, Grady and I enjoyed sitting down with former Illini and current NFL tight end Tip Reiman to kick off our second season of the podcast. You can catch the “Life Well Led” podcast on Spotify, Apple Podcasts, or YouTube (where you can see Grady sporting his favorite Jordan t-shirt).

Carry on fellow travelers, we’ll talk soon.