A recent study found that even one AI interaction made users more sure they were right.

Just as AI is trained to please users, teams are "trained" to affirm the boss, leaving leaders overconfident.

The resulting "Confidence Trap" isn’t a character flaw: It’s a natural consequence of how systems work.

The fix: Assign people to dissent, examine what your organization rewards, prompt for disconfirming data.

This post is co-authored by Emily Irving and Jeff Wetzler.

Imagine you're wrestling with a difficult organizational decision and decide to stress-test your thinking with an AI assistant. You explain your reasoning, share the plan, ask for feedback. The AI engages thoughtfully by refining a detail here, affirming your logic there, and it praises you for thinking through the situation so carefully. You close the laptop feeling sharper and more confident than when you opened it.

Most sophisticated AI users would recognize the trap immediately. This is called sycophancy: a model's tendency to tell users what they want to hear rather than what is accurate. A recent Stanford study revealed something even more unsettling than the sycophancy itself: what it does to the people on the receiving end. After just one interaction with an LLM, users became measurably more convinced they were right, less willing to examine their own role in a problem, and more likely to trust and return to the system that had affirmed them — even when it was distorting their judgment.

Now imagine a leader presenting a new strategy to her team. She walks through the plan, explains her reasoning, and invites reactions. One team member says the direction "makes sense" and asks a clarifying question about implementation. Another calls it "a strong foundation" and suggests a minor refinement. What neither says, though both are thinking it, is that they have serious reservations about whether the plan will actually work. They've read the room, sensed the leader's investment in the idea, and made a quiet calculation about what's (not) worth raising.

The........

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