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 works in other jobs. Mistakes at the CEO level can be fatal to your tenure.
2. Many CEOs resist the idea that they need training.
The classic trap is thinking that, since you got selected for the CEO role, you must already know how to do it. Success in previous positions creates confidence that can initially blind you to what you don’t know. But as mentioned just above, leading the whole organization is a difference in kind, not degree, from being responsible for one team or department.
The most frequent thing I hear from CEOs after we work together is “I wish I’d done this five years ago.”
3. Learner-CEOs are a distinct breed.
On the other hand, some CEOs love training. They tend (like me) to have a Learner profile. They’ll tell you the last five business books they’ve read and how each one influenced their thinking. They don’t see training as remedial but as a competitive advantage.
4. Training isn’t just for beginners.
The most frequent thing I hear from CEOs after we work together is “I wish I’d done this five years ago.” Time in the CEO chair doesn’t automatically equal mastery. Even excellent, seasoned CEOs can discover approaches that save time, reduce friction, and/or unlock the next level of performance.
5. Systems beat lists.
A list of individual lessons rarely sticks with a learner. But when concepts reinforce each other and connect into a coherent system, adoption becomes natural. CEOs need frameworks that work together, not a grab bag of tips.
6. The loneliest job craves community.
CEOs are isolated by the very nature of their singular role in the organization. But when you put them in a room together, magic tends to happen. For one, you get to interact with the small portion of the populace who understands the pressure of the job. And two, there is huge benefit in talking to leaders in other industries and with other areas of expertise. That kind of cross-pollination between disciplines is always how the best ideas and innovations and breakthroughs come about. As Charlie Munger said, “You must know the big ideas in the big disciplines and use them routinely — all of them, not just a few.”
7. Training and coaching are not the same thing.
Training teaches the CEO a system. Coaching helps the CEO get a listening ear and accountability through specific situations. Both are valuable, but they serve different purposes. Training requires someone who has extensive experience as a CEO; coaching does not.
8. Application matters more than inspiration.
The classic thing that happens with training is getting energized in the moment, then going back to your office and… immediately reverting to old habits. If I’m not working with CEOs to develop realistic plans and give them tools they will actually use, it’s just a motivational speech.
9. A good chief of staff is like gold.
Implementing new systems requires organizational muscle. There’s no rocket science happening in the CEO system I teach, but it does require discipline to get it up and keep it running. A chief of staff who understands the system and can help you communicate, organize, and follow-through is a game changer.
10. The CEO job is won or lost in your head.
From the mental models you use to make sense of your business and team, to your capacity for the kind of mindfulness my CEO-S cofounder Sherif teaches, your success as CEO depends greatly on what’s happening between your ears. The technical aspects of being CEO are learnable, but mastering your internal game determines whether you actually succeed.
The technical aspects of being CEO are learnable, but mastering your internal game determines whether you actually succeed.
11. Crisis mode is too late for training.
When the board is questioning your future, training probably won’t save you. Training is much better for prevention. The time to build capabilities is before you’re drowning, not after. Training helps you avoid shooting yourself in the foot, but only if you do it before pulling the trigger.
12. Avoiding common failures is most of the game.
Otto von Bismarck said that “Only fools learn from their own mistakes. The wise learn from others’ mistakes.” Or as Shane Parrish said more recently, “It can be difficult to appreciate how much simply avoiding the standard ways of failing dramatically increases the odds of success.” This truth is why a good deal of my CEO training covers the common failure modes. Learning the common failure modes means you don’t have to experience them personally to avoid them.
Between 50-70% of CEOs fail, but you don’t have to become a statistic.
I’m a firm believer that good CEO training can put even really good CEOs ahead of the game.
Want to join us for an upcoming CEO Masterclass? Email me at joel@ceosys.co. I am happy to send you a brochure and answer any questions you have.