The Coaching Paradox

It’s not easy, but embracing paradox might be the most important thing you can do to improve your coaching.

The best coaches are walking paradoxes.

We typically think of heroes and villains as opposing forces. In any good story, it’s protagonist vs. antagonist. Hero vs. villain.

Even in real life, there are heroes and villains. But not every single person is a hero nor a villain. Most people fall somewhere in the middle.

If we were to plot this on a graph, it would look like this:

But in the world of coaching, it’s not so black and white.

Take Bill Belichick, for example.

Belichick has won 6 Super Bowl titles, more than any other coach in history. That should make him a hero, widely respected by football fans everywhere.

Except in many circles, he’s a villain. Whether it’s because of Spygate, Deflategate, or his ho-hum demeanor with the media, people don’t like him.

This is further complicated by the fact that some people (like me) think of Belichick as both a hero and a villain at the same time. I appreciate both his coaching genius and dislike him for the scandals that have followed him throughout his tenure in New England.

If we were to plot Bill Belichick’s dual identity as hero and villain on a graph, it would look like this:

This type of pattern is repeated throughout sports history. Almost all of history’s best coaches exhibit paradoxical traits.

Nick Saban: Beloved leader and Extremely disagreeable figure

Gregg Popovich: Authoritarian and Nurturing leader

Brad Stevens: Nerd and Strong Former Athlete

Most leadership books and how-to books written by successful coaches or business leaders make our job as coaches black and white.

  • Be mean or nice
  • Be the authoritarian or the nice guy
  • Be the hero or the villain
  • Be “analytical” or “intuitive”
  • Meticulously detail-oriented or big picture visionary
  • Extroverted or introverted
  • High-energy or relaxed
  • Fun-loving or stoic

The truth is much more nuanced than that.

It’s not as simple as being one or the other. At least, not if you want to be a great coach.

Great coaches often exhibit seemingly opposed traits–often at the same time.

One moment Gregg Popovich will light up one of his players for making a crucial mistake. The next, he’ll throw his arm around that same player and remind him how much he cares about him.

Phil Jackson demonstrated this perfectly in Eleven Rings. Jackson wrote:

“One of the players I came down especially hard on was Lakers forward Luke Walton. I sometimes played mind games with him so that he would know what it felt like to be stressed out under pressure. Once I put him through a particularly frustrating series of exercises, and I could tell by his reaction that I’d pushed him too far. Afterward I sat down with him and said, “I know you’re thinking about becoming a coach someday. I think that’s a good idea, but coaching isn’t all fun and games. Sometimes no matter how nice a guy you are, you’re going to have to be an asshole. You can’t be a coach if you need to be liked.”

Jackson knew the importance of paradox in coaching. He knew that he couldn’t just be the Zen Master. He also had to come down on his players hard when it was called for.

This is uncomfortable for many. We want leadership to be clean and tidy, not so messy.

Unfortunately, leadership is messy. Without a tolerance for nuance and paradox, we’ll feel stuck as we struggle to lead our teams to where we want to go.

We all want to be the nice guy. But sometimes, like it or not, “you’re going to have to be an asshole.”


The idea for this article came from Chapter 14 (“The Founder’s Paradox”) in Zero to One by Peter Thiel.