Drill Makes Skill: The CEO's Practice Ground

There’s an old joke: “How do you get to Carnegie Hall? … Practice.”

I often think about that when coaching CEOs. Over the years, one thing has become crystal clear: The skill of being a CEO isn’t something most of us are born with, and it certainly doesn’t arrive fully formed on day one. It’s a craft, one honed through repetition, reflection and deliberate adjustment. 

In other words - practice.

But unlike musicians or athletes, CEOs rarely get to rehearse in private. Every decision is live, every call is visible, and the stakes are high. Investors, employees, customers, everyone is looking to you for the answer. No wonder so many CEOs feel like they’re expected to “just know”.

The truth is, nobody just knows. What separates CEOs who thrive from those who burn out isn’t brilliance alone, it’s their ability to deliberately practice their craft in safe spaces, without putting the company at risk.

Safe Spaces Are Where Growth Happens

Creating a “safe space” is the ultimate lever for CEO development. These are environments, peer groups, mentors, or executive coaching sessions where you can stress-test ideas, rehearse conversations and explore blind spots without consequences. Safe spaces give you the freedom to experiment, make mistakes and learn exactly the way a musician or athlete does during practice.

Don’t get me wrong: just because I call these environments “safe spaces” doesn’t mean you aren’t tested to your limits. The point is not comfort - it’s challenge without catastrophic risk. You’ll be pushed, questioned and confronted with tough truths, but in a way that sharpens your judgment, hones your decision-making and accelerates your growth without putting the company on the line.

But a safe space isn’t enough on its own. To make your practice effective, it needs to be supported by these three key habits:

1. Focus on what's most important at your stage of growth

A safe space works best when you bring the right challenges into it. The levers that matter at $2M ARR are very different from those at $20M ARR. Decide what’s truly critical, product-market fit, go-to-market motion, cash management or leadership development, and practice thinking and problem-solving around those.

2. Surround yourself with exceptional talent

Practicing as a CEO isn’t about doing everything yourself, it’s about practicing leading. Surround yourself with a highly talent-dense team that you trust to execute. This gives you space to step back, experiment with decisions and refine your judgment without the risk of a weak bench failing to execute and undermining your learning.

3. Build an adaptable strategy and execution systems

Safe practice is amplified when paired with strong operational habits. Use your safe space to review and refine strategy, test new ideas and iterate execution systems. This builds the muscle memory for making decisions that are both bold and grounded, without endangering the business.

Drill makes skill.

CEOs who embrace safe spaces, don’t just survive - they thrive. Practicing deliberately in the right environment allows you to build mastery, resilience and judgment all while giving your company the best chance to succeed.

Photo Credit: Eduardo Cano Photo Co.