A few months ago, as ski season in New England was winding down, I found myself thinking back to my college days teaching skiing at Okemo in Vermont. One lesson from those years has stayed with me for all these years and had a much broader application than skiing itself.
We learned if you wanted to improve your turns, you didn’t try new techniques on the steepest trails on the mountain. You started where the terrain was manageable enough to practice fundamentals where you could be in control of the situation.
On easier trails, skiers could confidently try something new without fear of getting out of control. They could make mistakes, adjust, and try again. Over time, confidence grew because the repetition built competence. Only then did we move on to the harder terrain.
By the time someone reached a challenging run for them, the fundamentals had become ingrained. They had practiced enough to stay composed when the terrain became steep or narrow or icy (this is Vermont after all).
Over the years, I’ve come to believe leadership develops much the same way.
Most CEOs are asked to develop judgment while already carrying the full weight of the role. There is no practice season for difficult leadership decisions. You don’t get a rehearsal before a major acquisition, a downturn, a leadership breakdown, or a tough board conversation. Many CEOs encounter these moments for the first time while the stakes are already high.
That’s part of what makes the role uniquely challenging. It’s not just the pressure. It’s the expectation that you should already know how to navigate situations you may have never seen before.
And unlike many professions, CEOs often have very few places where they can openly work through uncertainty before acting. As we often say, there is no CEO school. The role is completely different from other roles they held on the way to the CEO seat. As a result, many leaders are forced to learn on the hardest slopes.
When people talk about experienced CEOs, they often assume experience simply means years in the seat. I don’t think that’s the only way to gain experience.
What builds judgment is repeated exposure to difficult situations combined with the ability to reflect on outcomes over time. Leaders begin recognizing patterns. They learn which instincts serve them well, where blind spots tend to emerge, and how decisions play out beyond the immediate issue in front of them.
That kind of learning happens gradually through observation, conversation, and accumulated experience. It’s also one reason I’ve always believed peer groups can be so valuable for CEOs. When leaders hear others work through acquisitions, succession issues, cultural challenges, or stalled growth, they build perspective long before those exact situations arrive in their own business.
In many ways, it’s the leadership equivalent of learning on the easier slopes first. You develop the fundamentals and judgment in environments where there’s room to think, reflect, and learn before facing the steepest terrain on your own.
One misconception about strong CEOs is that they operate with certainty all the time. In my experience, the best leaders are not necessarily more certain than everyone else. What they often have is greater confidence in their ability to work through uncertainty because they’ve spent years developing judgment and resilience.
That confidence usually looks quieter than people expect. It’s less about bravado and more about composure.
The CEO who has spent years learning from difficult situations and reflecting on decisions tends to approach pressure differently. They don’t panic as conditions change because they trust their ability to navigate complexity, even without perfect information.
Skiing works the same way. The skier who handles difficult terrain with calm and control usually developed those skills long before reaching the steep couloirs I love skiing at Alta. The confidence comes from repetition, fundamentals, and time spent learning where mistakes were easier to recover from.
Every company eventually runs into periods where leadership gets tested. Sometimes it comes through a market shift or the unexpected departure of a key executive. Other times, it’s more subtle. Growth slows, alignment weakens, or decisions that once felt straightforward suddenly carry more weight.
The CEOs who navigate those stretches well are rarely figuring everything out for the first time in the moment. More often, they’ve spent years building the judgment and perspective those situations require.
And like skiing, most of that preparation happens long before the hardest run appears in front of you.
