Know When to Hold and When to Run: Lessons in Leadership from the Sports Pages

Articles from the Sports Sections of the Chicago Tribune and other news outlets offer insights into leadership, management, and staffing challenges that excite me daily.

This week, two compelling stories echo the wisdom of Kenny Rodgers’ lyrics:

“You’ve got to know when to hold ’em Know when to fold ’em Know when to walk away and know when to run.”

Story One: A valued sports TV play-by-play announcer makes a bold move.

“The (Detroit) Tigers hired Jason Benetti from the Chicago White Sox on Thursday, signing one of the country’s most respected broadcasters on a multiyear contract.”

Why did he walk away?

‘They want to put together a telecast that is phenomenal. I wouldn’t have taken the job if that weren’t the case.’ Benetti said.

The Tigers presented Jason with a compelling vision. However, his decision to walk away wasn’t easy.

Jason shared, ‘This is right. And I can’t believe it’s right, because I’m leaving home. Please don’t underestimate how much I have to feel this to leave (home).’ (Evan Woodbery ewoodber@mlive.com, Nov. 09, 2023)

Story Two: Brewers manager transitions to become the Cubs manager.

Craig Counsell left his position as the manager of the Milwaukee Brewers to take on the role of the Chicago Cubs’ manager. Why? Meghan Montemurro of the Chicago Tribune reported that Chicago Cubs President Jed Hoyer’s vision for the Cubs’ future convinced Counsell. ‘I wanted the challenge of this, all this,’ Counsell said. ‘My hope is the pressure to win in Chicago is just the pressure to win in Chicago. I don’t need any more than that.” Yet, Montemurro points out, “Counsell underestimated how Brewers fans would take his departure for a rival. A frosty reception likely awaits Counsell during his first trip back to American Family Field.”

These stories are particularly relevant for my current client, “Michael.” He finds himself in a business that has struggled for a decade, and he is holding on. What might prompt him to fold and walk away? Perhaps these stories can provide guidance. Benetti and Counsell stayed with what they had (though wonderful) until something better came along, then they seized the opportunity.

After gaining insights from these stories, Michael is now exploring options that offer a vision that inspires him and makes it worthwhile not just to walk away but to run!


Chuck Scharenberg is the Founder of More Profit More Freedom, a consultancy that assists new C-suite executives in scaling their businesses by constructing cohesive teams and sustainable infrastructures.