by Michael Holland    

Chris Rock is renowned for his comedy.  He walks effortlessly through his acts, entertaining tens of thousands of fans, and while his humor is definitely well-known, the way that he creates his comedic routines is a little more obscure.  Chris works a methodology that forces him to go on little-known stages and fail tremendously in front of a tough crowd.  Chris’ preparation process seeks a series of little wins, a phrase here or a portion of a joke there, that catches the tiny audiences just for a moment.  Night after night, Chris tests more and more material, failing miserably in order to gain a single win.  He’s making lots of little bets and failing fast.

Our next generation of leaders, those newly promoted rookies, should be allowed to fail quickly and often. They should make lots of these little bets. Our next generation leaders should train like Chris Rock in these three ways.

  1. Their practice creates wisdom.  Newly promoted leaders need to get their leadership legs under them.  They need to immediately begin practicing those skills which will allow them to best understand their strengths and challenges as a leader.  Practice means doing, not simply watching others do.  Every opportunity to run a meeting, plan a project, schedule workloads, and lead technical reviews creates the slice of time for little wins or little losses.
  2. Their naivety allows for creative communication patterns.  Communication skills are critical in leadership.  Unencumbered by the weight of mistakes, new leaders will try to communicate in very authentic ways, allowing these leaders to make little bets and see firsthand what works and what falls flat.  Communicating well requires a combination of art and science, and these are great coaching moments for their ever-so-smart boss to leverage as they mentor the new leader.
  3. Their failings will open opportunities for honest feedback.  New leaders should be pushed to immediately provide feedback to employees as much as possible.  The new leaders need to work quickly to understand how to give praise, advice, and correction for given situations.  Failing fast and often with minor feedback sessions – any minute of any day – lets the leader learn to recognize how people react differently to varying levels of feedback.  They will quickly see and feel how feedback impacts others even though they won’t necessarily understand why.

It may be hard to imagine the great Chris Rock standing on a small stage, purposely making little bets to see what jokes bomb and what jokes work.  But he does it, and more importantly, he does it intentionally.

Let’s help our next generation of leaders to become the best leaders they can be by encouraging them to fail… and fail… and fail.

And then succeed.

Coaching Thoughts- For You and Your Peers

  • Think back to one of your failures as a leader. Did it help you to improve in any of the three ways listed in this leadership learning moment? If so, how?
  • Which of these three small bets do you find most insightful? Why?
  • The following phrase near the end of this post refers to his practice of failing over and over in small ways to gain the big win: “…he does it, and more importantly, he does it intentionally.” Is the intentionality important? Why or why not?