Dear Friends,

I grew up watching the tennis greats of yesteryear with my dad, but have only returned to the sport recently thanks to another family superfan, my wife. So perhaps it’s understandable that to my adult eyes, it seemed like the current crop of stars, as awe-inspiring as they are, don’t serve quite as hard as Pete Sampras or Goran Ivanisevic. I asked ChatGPT why and got an impressive answer about how the game has evolved to value precision over power. Puzzle solved! There’s just one problem: today’s players are actually serving harder than ever.

So why did ChatGPT feed me misinformation?

Because I asked a leading question—and it told me what I wanted to hear. Not because it’s broken, but because that’s how it’s built.

Large language models like ChatGPT are trained using a process called Reinforcement Learning from Human Feedback (RLHF). In theory, it aligns AI with human values. In practice, it rewards answers that feel right more than those that are right.

And when users feel affirmed, they upvote the response. The model learns that flattery works—even if it’s wrong.

Now imagine you’re a CEO or senior leader using AI to gather insights, test decisions, or validate strategy. The very same systems are likely reinforcing your preexisting beliefs—and doing it faster, smoother, and more convincingly than any human advisor ever could.

This is a serious problem.

The best leaders don’t surround themselves with flatterers. They build teams where disagreement is safe and dissent is welcome. Amy Edmondson’s foundational research—and Google’s own Project Aristotle—found that psychological safety is the most important factor in team performance.

Great leaders—from Lincoln to General Stanley McChrystal—sought out people who disagreed with them. They wanted to be challenged, not coddled.

But AI doesn’t challenge you. It affirms you. Persuasively, even eloquently. And that makes it even harder for leaders to stay grounded in the humility that true leadership requires.

So how do you counteract this?

Simple, but not easy: remember that your tools are still only as good as your questions.

Sometimes the most important words a leader can hear are: “I don’t think that’s right.”

Seek out dissent. Reward discomfort. And when an assistant—human or digital—tells you you’re wrong… listen.

—Gautam

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Further Reading….

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