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.
“That’s the issue,” Jill said. “A lot of times, he just doesn’t. He always seems to be out front, on his own. It’s always his way of doing things, his ideas taking center stage, his decisions being the final word. And what makes this so hard is that most of the time, he’s right. He’s incredibly knowledgeable, and his decisions get us where we want to go. But the way he communicates and the way he comes across is causing friction—with his peers and on his team, too. As good as Philip is, we simply cannot have this kind of dynamic from our leaders.”
I asked her to elaborate on his communication style and describe how he comes across.
“He can be very condescending,” Jill said, “and candid to the point of being rude. You know that expression about not suffering fools gladly? That’s Philip. He has no tolerance for anybody he thinks is incompetent or uninformed, which is one of the reasons he always feels the need to weigh in. There was a meeting with senior leadership recently, where we apparently weren’t moving fast enough for him. He went on a rant about how the solution was ‘abundantly obvious’ and why didn’t we just do so-and-so and it would be resolved. He called out several people, including the person leading the meeting, for being ill-prepared, and said the whole thing was a waste of time!”
“Have you shared any of this feedback with him?” I asked.
“I have,” said Jill, “but nothing’s changed. I’m not sure he gets it. Or maybe he does but doesn’t think it’s a problem because his results speak for themselves.”
When I later met with Philip, his confidence—and his blind spot—were immediately apparent. “I don’t understand what the problem is,” he said. “I deliver. My team delivers. We’re hitting every metric. Isn’t that what matters?” He paused and looked at me expectantly. I asked him what success looked like for the broader organization, not just his function. He talked about growth targets, market share, and technological excellence—but when I asked about collaboration, morale, and leadership alignment, he hesitated.
Philip’s blocker was the belief “I know I’m right.” It had served him well early in his career, when being the smartest person in the room meant faster solutions and visible wins. But at the executive level, where results depend on mobilizing others, the same belief became a liability. His certainty left no room for others’ ideas, eroding trust and stifling innovation. It wasn’t that Philip was wrong—it’s that he needed to be less right, more open.
Over time, Philip came to see that leadership at scale isn’t about personal accuracy; it’s about collective efficacy. He learned to ask, “What am I missing?” and “How can I bring others in sooner?” His teams began to respond differently—meetings became more participatory, and collaboration improved. When Jill later reflected on his progress, she said, “It’s not that Philip changed who he is; it’s that he shifted how he shows up. He’s learned that being right isn’t the same as being effective.”
The lesson here is one that many senior leaders can relate to: mastery can become a trap. What once made you successful—certainty, speed, and control—can undermine you when influence, empathy, and trust are the real differentiators. The most effective leaders know when to lead from the front and when to pull back and draft with the peloton.
