12 Things I've Learned from Training CEOs

On November 5–7, I am teaching my CEO operating system in a training outside Austin.

There are a couple of spots left for motivated CEOs who want to start 2026 with a new playbook for delivering performance.

The session includes private lodging, meals, and time for rest and mindfulness.

Email me if you would like more info or to attend.

As our next CEO Masterclass approaches, I’ve been reflecting on what I’ve discovered about training leaders for the past 10 years.

This work has been among the most rewarding of my career, and it’s revealed patterns that most people outside this world never see.

After years of training CEOs across industries, here’s what I’ve learned.

1. Most attendees have zero prior CEO-specific training.

This makes sense, as there are no training wheels for the job. You can’t be a junior CEO. There’s no practice round. The role is fundamentally different from every executive position that came before it, and the stakes don’t allow for the learn-by-failing approach that wo…