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CommentaryLeadership

I’ve interviewed 700 leaders. The ones outsourcing their thinking to AI lose their best people first

By
Ryan Hawk
Ryan Hawk
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By
Ryan Hawk
Ryan Hawk
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July 20, 2026, 7:30 AM ET

Ryan Hawk has interviewed over 700 leaders and high performers on The Learning Leader Show, a top-ranked management podcast. He is the author of The Price of Becoming: The Compounding Practices of High Performance.

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Ryan Hawk has interviewed over 700 leaders and high performers on The Learning Leader Show.courtesy of Ryan Hawk
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I’ve spent the last 12 years interviewing more than 700 leaders for The Learning Leader Show. I’ve started noticing the same failure pattern across founders, executives, and managers alike: some of them are outsourcing their thinking to AI, and their best people are the first to notice. 

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You can outsource almost all your thinking to AI. With Claude, Gemini, or ChatGPT, answers are instantaneous. But you can’t outsource your own understanding. Credible leaders build trust among employees, investors, and the general public through translating data into meaning. By conveying that meaning, they build motivation, inspiring others toward a shared vision. This is a human skill that AI lacks.

At the beginning of every new coaching gig with leaders, I ask the same question: “What is your writing practice?” I start here because I know that writing, by forcing messy thoughts out of your head and onto the page, creates clarity. As a leader facing overwhelming complexity, you don’t know what you think until you can explain it in simple terms. 

Answers have always been available. Books, essays, and podcasts have made the management and leadership knowledge of the greatest minds in history a click or two away. But your team doesn’t want leaders who just give out answers. They want to work for people who truly understand the product, the market, the job. People who have faced the same day-to-day struggles and can speak to all of them honestly.

Charlie Munger would often tell the apocryphal story of Max Planck and his chauffeur. Planck, bored of giving the same lecture on quantum mechanics over and over, handed the job over to his chauffeur, who had memorized it after hearing it so many times. Planck himself sat in the audience, wearing his chauffeur’s hat, as his driver delivered the familiar speech word for word.

Then, during the Q&A, a member of the audience asked a difficult physics follow-up.

“I’m surprised that in an advanced city like Munich I get such an elementary question,” the chauffeur said. “I’m going to ask my chauffeur to reply.”

There’s a difference between repeating a sequence of words and understanding something deeply enough to answer questions about it and defend your reasoning. It’s the difference, as Munger put it, between Planck knowledge, “the people who really know, they’ve paid the dues, they have the aptitude,” and chauffeur knowledge. If you want to understand something, you have to earn it.

I’ve watched this happen up close. A CEO I know started using AI to write his speeches and company-wide emails. His people could tell right away. The words were polished but didn’t sound like him. Employees began deleting his emails without reading them. They stopped paying attention during the virtual townhalls, or they would multi-task. His leaders lost respect for him because he had outsourced one of the most important parts of the job. Worse, they lost confidence in the future of the company. If the CEO wasn’t willing to think hard about where they were going, why should anyone else?

When a leader can speak authentically and meaningfully about overcoming challenges, we are inspired to match their efforts. Think about a great accomplishment in your life, one that still fills you with pride: winning a championship, getting an A+ in chemistry, earning a big-time promotion at work, hitting a big squat PR. Without exception, that feat was preceded by a ton of effort. More important than the outcome was the fact that doing this work changed you for the better. Among other things, it gave you the authority to speak about what it takes to accomplish hard things.

In a recent interview, author David Sedaris recalled telling a friend he’d spent the afternoon going to the post office.

“Why would you do that?” the friend replied. “You don’t need to go to the post office. If you have something you want mailed, you have the hotel call FedEx, and they come and pick it up.”

“I don’t want to live like you,” Sedaris said. “I want to go to the post office. And I went to the post office, and it was remarkable. Or sometimes you go to the post office, and the person is just grumpy, and you can even get something out of that.”

If we “use all the shortcuts,” Sedaris is saying, we start losing the plot. We eliminate any possibility of experiential learning. By outsourcing our thinking to AI, we remove friction. Growth happens because of friction. Don’t remove friction if you want to grow. People are messy. How are we going to get better at dealing with that messiness if we remove the mess from our own lives? We have to live before we lead.

When everyone has chauffeur knowledge, people are going to follow leaders who actually did the work to understand. AI can give you good information, but the human part? The connection with another person? Human beings will always value that more. We want it more now than ever. We’re tired of our screens and yearning for IRL experiences. Concert ticket prices have risen 4 times faster than inflation over the past three decades. Since the 1994 World Cup, U.S. ticket prices have jumped 1,000%, while household incomes grew only 32%.

Outsource your thinking long enough, and you will inevitably land in a place where you have no genuine understanding of what you’re doing, where you’re going, or how you’re going to get there. What kind of leader will you be then?

Like Planck’s chauffeur, AI will happily tell you what to think, do, or say. But phoning it in this way will never inspire anyone else to build on what you’ve accomplished, which is a core function of leadership. Your team will spot the chauffeur at the podium, and that will sap their trust in you faster than any genuine error in judgment you might make as a leader. Your smartest and most perceptive employees will be the first to run for the door.

The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

Ryan Hawk has interviewed over 700 leaders and high performers on The Learning Leader Show, a top-ranked management podcast. He is the author of The Price of Becoming: The Compounding Practices of High Performance.

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