CEO Coaching: Your Personal Operating System

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 to skid off the rails. As I’ve said before: trusting your gut only works if your gut has digested a steady diet of learning and experience. Otherwise, you’re just asking for a messy outcome. (And yes, I mean disaster.)

Spend time with a seasoned, successful CEO and you’ll find they’re not winging it. They’ve built—consciously or not—a set of beliefs, principles, processes, and routines. That’s their operating system. It helps them swat away curveballs, think strategically, hire smart, and lead without setting the place on fire.

Let me illustrate: One of the many cats we’ve had over the years—Barney—was dumb as a doorknob. Sweet, but dumb. Everything terrified him. Loud noise? Scary. New couch? Scary. Same couch the next day? Still scary. He had no internal file system—no learning, no processing, just panic. Don’t be a Barney.

The best CEOs? They share a few traits that make them more effective and less like confused felines:

• They’ve done the values work. Ask them what they stand for and they don’t need a whiteboard session. It’s internalized and consistent.

• They’re curious as hell. Constantly vacuuming up data, trends, feedback, and experiences. Then they synthesize all that into actionable beliefs. This saves time and builds consistency. (But beware: when beliefs calcify into dogma, it’s time for a reboot.)

• They build and follow process. Not because it’s fun, but because it works. Decisions, planning, meetings, one-on-ones, financial reviews—there’s a method to the madness. Think of it like a pilot’s checklist: critical when skies are clear and downright essential when the engines sputter.

• They develop effective routines. Not in a robotic way, but in a way that gives them control over their time and offers predictability to their teams. They also know when to change things up—because adaptability is part of the OS, too.

A few coaching clients have gone the extra mile and written all this down. We review it together and fine-tune. I recommend doing the same. Codify your personal OS. You’ll still be dealing with chaos (welcome to leadership), but it won’t own you.

And you won’t end up like Barney—hiding under the bed every time the wind blows.