I’ve worked with young executives—yes, even CEOs—who are undeniably smart but utterly unmoored in how they lead and manage. What’s missing? A personal operating system. Not some productivity app with a quirky name, but a real internal framework that guides their decisions and behavior. This is where bright, energetic founders—with little or no management seasoning—start […]
As our current administration continues its whiplash-inducing habit of making knee-jerk decisions, many businesses are being upended—or made irrelevant. Some probably deserve it. Many don’t. If you’re leading a company caught in the crossfire of regulatory, financial, or political chaos, it’s time to ask a hard question: Is your business model still the best way to […]
Dogs are loyal. Painfully loyal. If you want to test just how loyal, try this (hypothetically!): lock your spouse and your dog in your trunk for an hour and see who licks your face when you let them out. (To be clear: I do not condone locking up spouses, dogs, or even cats—despite my personal reservations about […]
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 […]
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 […]
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 […]
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 […]
The passing of Jimmy Carter got me curious about his life. I’ll admit, my initial take on him was shaped by secondhand opinions and headlines. “Bungler as a president,” they said. Sure, I admired his post-presidency contributions—Habitat for Humanity volunteer, Nobel Prize winner, peacemaker, Sunday school teacher—but as a leader? My verdict was: good guy, […]
On a trip to Cuba this year, I spent a day and a half in Havana with friends before boarding a boat for some fly fishing in the flats, far offshore. It was both fascinating and unsettling. Many of us, as Americans, likely have an image of Cuba that’s a mashup of cigars, rum, classic […]
In my work with leaders across various organizations, I often interact not just with the CEO but also with a layer or two deeper within the organization. Sometimes, there’s a disconnect between the C-suite and those who are responsible for executing the strategy, leading to inevitable frustration. There are two questions that, if answered, can […]