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10/29/2025

The Cost Of Certainty

Why great leaders learn to step back

Philip was the senior vice president of technology for a well-funded, growing startup that pioneered solutions in an untapped market. When Jill, the chief information officer, hired Philip to join the leadership team, it was because of his experience taking technology ideas from inception to market, as well as the innovations he had led in his past roles. Jill called me after sharing her observations about Philip with her own executive coach, wondering if maybe Philip could benefit from coaching.

“Philip is great,” she said. “This is not about fixing something that’s broken. In fact, I can actually see him succeeding me one day. He’s critical to our success, especially as we look to position ourselves for an IPO. But for us to meet the aggressive growth targets we’ve established, I need us to be moving like a peloton, in the original sense of the word. Because even one rider’s behavior can significantly impact the outcome of a race.”

In road-cycling races, a “peloton” refers to the main pack of riders that forms as they draft off each other to reduce wind resistance and improve overall efficiency. Teams use the peloton strategically to conserve energy and position themselves for key moments in the race, such as sprints or mountain climbs. Jill wanted her organization to work in the same way. “So, where does Philip fit in this peloton?” I asked.

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