The Iteration Game

Playing the iteration game makes you fearless and egoless—the pinnacle of leadership.

My friend Robbie Crabtree is an attorney who has worked over 100 jury trials in law career. Over the past decade, he’s honed his speaking and persuasion skills, and now runs a wildly successful and transformative online course called Performative Speaking. Back when the idea for his course was just a seed in his mind, we spoke about what it takes to become a great speaker. To paraphrase his advice, it came down to the simplest approach that few people take: put your reps in. Iterate, repeat.

You now know that modeling yourself after your heroes is essential to the process of defining your own leadership style. Kobe Bryant looked to Michael Jordan and Magic Johnson. Dave Chappelle looked to Eddie Murphy and Richard Pryor. Robbie looks to TV shows like The West Wing and Suits. Every great leader and performer shamelessly imitates their heroes before they can achieve their own authenticity. But stop at imitation, and you risk being seen as inauthentic and fraudulent. Iteration is the necessary next step. It requires you to take what you learned from imitation and continuously repeat, zooming in on those moments of friction, fixing, adjusting, and honing them with each repetition until you reach your intended effect. Notice I didn’t say perfection. It is in your moments of imperfection where your authenticity shines through. Kobe became great through his imperfect Jordan impersonation. Chappelle became great through his imperfect Pryor impersonation. Robbie became great through his imperfect Harvey Specter impersonation. Imitation is nothing to fear, as long as you iterate. And it is through your relentless iteration that you achieve your authenticity.

It’s through relentless iteration that you also dissolve fear. By facing your imperfections over and over again, making mistakes, and willing to handle the consequences, you remove the friction of relentless iteration—a virtuous cycle. The more you iterate, the more comfortable you get. The more comfortable you get, the more you iterate, and the closer to greatness you will come. You must step in front of that microphone with confidence. You must parachute from that plane with self-assurance. You must step into the bullring with determination. Day after day. By removing fear from the equation, you remove yet another barrier that traps most people in mediocrity. By removing fear from the equation, people will naturally follow your lead.

By iterating, you also dissolve your ego. One of the biggest mistakes leaders make is thinking they have it all figured out. They become so sure of themselves and so sure of their plan, that they discount the possibility that anything could go wrong. Their ego causes them to become rigid in their ways and unable to adjust in critical situations. But through relentless iteration, you become mentally agile. You become a better iterative decision-maker—an invaluable skill as a leader. You repeatedly subject yourself to the embarrassment of your mistakes, you cultivate an ability to admit when you are wrong, and you fuel your drive to become better with each attempt.

Even after five championships and 18 all-star appearances, Kobe was still the first one in the gym every morning and the last one out every night, always striving for that impossible perfection of Jordan, always seeking to transcend his game, always pushing his teammates higher than they thought was possible. Chappelle, with all the money, fame, and skill one could ever imagine, was still showing up at hole-in-the-wall comedy clubs to iterate and hone his craft when everyone else thought he’d already attained perfection. Even Pablo Picasso himself iterated, not as a means to achieve perfection, but in pursuit of essence and meaning. And in doing so, he transformed and transcended his craft forever.

Leadership isn’t something you do. Nor is it something you strive for. To do so is to walk on thin ice—you’ll fall in at the slightest sign of pressure. Leadership is honing your craft before you ever think about leadership. It’s about building a foundation of skill and competence so impenetrable that no one can question your authority. And it’s about leading by example with humility and courage. To ever be considered a leader, you must first be considered great. And to be considered great, you must play the iteration game.

Like Robbie. Like Kobe. Like Chappelle. Like Picasso. Greatness iterates relentlessly.

Put in your reps.

Iterate.

Repeat.