The Certainty Trap

On expertise, overconfidence, and the decisions AI cannot make

Part 2 of the BAI Leadership in the Age of AI Series | Following: The Answer Machine (7 March 2026)

There is a particular kind of executive who isn’t worried about AI.

Not because they’ve thought it through. Because they haven’t needed to. They’ve been right too many times, in too many rooms, for too long. Their pattern recognition is fast. Their network is deep. Their reputation precedes them in ways that have made sustained self-examination feel unnecessary. They are, in the fullest sense of the phrase, a comfortable expert.

They are also, the evidence increasingly suggests, the ones most at risk.

The Reversal Nobody Expected

Last Sunday’s The Answer Machine piece drew responses from people who recognised the anxiety — the quietly unsettled leader watching AI synthesise in seconds what used to take days. But the more unnerving conversation is the one that isn’t happening. Because the leaders most exposed to the coming shift aren’t the ones who feel the ground moving. They’re the ones who can’t feel it yet.

A study published in late 2025 in Computers in Human Behavior produced a finding that should give any experienced executive pause. Researchers at Aalto University asked…