Allow the Struggle or Cushion the Fall?

Published: January 24, 2023

Generational succession planning has left Baby Boomers with a conundrum. As the 60-somethings exit their leadership positions, they must decide how much guidance to provide the 40-somethings. These whippersnappers will likely own decision authority for the next two decades. Imagine the consequences in a family business where the heir doesn’t need to be qualified to get the job. Gulp.

Painting by Frida Kahlo

This painting adorns a local restaurant near our offices where a similar succession plan is underway. The heir to the throne is both scared and stoic. The future triggers both anxiety and excitement. She must display both authenticity and confidence. The nagging nudge of imposter syndrome is real. She isn’t sure she can navigate the future but has no choice.

At some point, we’re all thrown into the deep end of the metaphorical pool, and it’s up to us whether to sink or swim. All versions of performance anxiety tell the same story. We feel like imposters because we are imposters – until we’re not.

The next generation of leaders should spend as little time as possible under the wings of their mentors. The knowledge and experience to be learned has already been bestowed. The real learning happens by doing. Make some mistakes. Screw up something with big consequences. That is how true growth unfolds.

It’s always an option to bubble-wrap your successor. But you can only cushion so many falls. Eventually, we all need to learn how fall and then, how to get back up. Accommodating uncultivated skills only prolongs skill development. Struggle is the best teacher.

Photo of Steve Ritter, the co-founder of The Center for Team Excellence

Steve Ritter

Steve Ritter is an internationally recognized expert on team dynamics whose clients include Fortune 500 companies, professional sports teams, and many educational organizations. He is on the faculty of the Center for Professional Excellence at Elmhurst University where he earned the President's Award for Excellence in Teaching. Steve is the former Senior Vice President, Director of Human Resources at Leaders Bank, named the #1 Best Place to Work in Illinois in 2006 and winner of the American Psychological Association's Psychologically Healthy Workplace Award in 2010. Steve provides ongoing workplace culture consultation to many thriving companies including Kraft Foods, Advocate Health Care, Kellogg's, the Chicago White Sox, AthletiCo, and Northwestern Mutual Financial Network.