Category: Blogs

CEO Coaching: Treading Water

Organizations get stuck. Not in-the-weeds, minor-speed-bump stuck, but full-body-in-quicksand stuck. Over time, layer upon layer of rational processes are put in place to support strategy and reduce risk. But let’s be honest: many of those “rational” processes also build moats around fiefdoms, create the illusion of certainty where chaos should thrive, and keep management happy […]

CEO Coaching: Yeah, It’s Complicated

Have you ever used the phrase “it’s complicated” with your spouse or a close friend when you couldn’t—or didn’t want to—explain something? It’s a total conversation killer. Unsatisfying for the listener. Evasive at best, lazy at worst. CEOs and other leaders are constantly told to simplify messages and use storytelling to unify and inspire their teams. I’ve […]

CEO Coaching: Humble Pie, Buffett-Style

I read Warren Buffett’s final Chairman’s Letter to shareholders the morning I wrote this. I’ve written about Buffett and his letters before, but this one hit me differently. For a guy who may be the most successful investor in modern history, Buffett is remarkably thoughtful—and humble. His annual letters are sprinkled with mea culpas about […]

CEO Coaching: Stuck in Chaos? Try This!

One of the many (many) jobs of a CEO is to bring order to chaos and provide clarity where turmoil reigns. The catch? True certainty rarely exists, and pretending otherwise is a fool’s errand. I don’t know about you, but my clients and I are getting downright exhausted by the chaos gleefully dumped upon us […]

CEO Coaching: Be Tough, Not an Ass

I don’t buy into gentle parenting, and I don’t buy into soft leadership either. Kind? Yes. Empathetic? Absolutely. Supportive? Of course. But tough? Hell yes. Mistakes shouldn’t be ignored. Feedback—both positive and negative—should come with real consequences. Leadership isn’t about hand-holding; it’s about setting expectations and enforcing them. That said, there’s a not so fine line between […]

CEO Coaching: Idiots at the Helm?

At a cocktail party recently, a guy I met launched into a monologue about his deep knowledge of the auto industry. I tuned out after a few minutes, but before I did, he confidently declared that the whole industry was run by idiots. Now, I’ve known, worked with, and worked for (and been one myself […]