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 preached it myself. And it’s true—leadership is partly about making the complex simple.

But here’s the thing: making something simple takes a ton of work and deep understanding.

I recently listened to the U.S. Supreme Court hear arguments in a fascinating case about whether a single district court judge has the power to block a policy nationwide (i.e., “universal injunctions”). The justices’ questions were steeped in constitutional law and decades of precedent. Portions of it flew over my head and around my vocabulary.

Yet when the case is decided, the headlines will probably scream something like: Supreme Court Moves to End (or Continue) Birthright Citizenship! And unless you’ve listened to the actual arguments—or at least read the transcript—you’ll likely walk away with a hot take on what happened and why.

Welcome to modern leadership. CEOs face a similar dilemma.

Senior leaders spend months shaping a company strategy, weighing data, debating tradeoffs, and considering blind spots—only to be judged by how they explain it in a 30-second elevator pitch. (See also: CEO Coaching: Idiots at the Helm?).

Yeah. It’s complicated.

Complicated issues can’t be ignored, and they sure as hell shouldn’t be decided with a coin flip. CEOs must be capable of wrestling with complexity, sometimes trusting their gut—but more often grinding through diverse perspectives, contradictory data, and political landmines.

Then comes the hardest part: crafting a message that actually lands. The job isn’t done until the idea is sticky. That takes persistence, insight, clarity, empathy, and compelling language.

So yeah, it’s complicated.

But that’s the gig.