The problem with executive judgment usually isn’t a lack of confidence. It’s that confidence and accuracy have almost nothing to do with each other.
For ten years, researchers tracked hundreds of CFOs at major companies, asking each one for a one-year stock market forecast along with a range they were 80% confident would contain the real answer. If they were even roughly right about their own certainty, the actual result should have landed inside their range 8 times out of 10.
It landed inside their range 36% of the time. Worse than a coin flip, dressed up as precision. And it got worse, not better, during the periods of highest uncertainty — exactly when a leadership team most needs to know how much it doesn’t know.
This isn’t a story about bad forecasters. It’s a story about how confidence gets communicated in business at all. Almost no one in a leadership meeting says “I’m 65% sure.” They say “this will work,” or “there’s no way that happens” — language that sounds decisive but hides how thin the actual evidence is underneath it. The false binary feels more like leadership. It’s actually just less information, wearing a confident voice.
Annie Duke calls the fix calibration in Thinking in Bets: forcing every belief into an honest probability instead of a flat statement, so the confidence itself becomes something that can be checked later. Her test for whether someone actually believes what they’re saying is simple — offer to bet on it, and watch how fast the certainty gets renegotiated. Most claims that sound absolute turn out to be a lot softer once money, or a real record, is on the line.
Two ideas worth carrying into the boardroom: Trade certainty language for a number. The next time someone says a plan will “definitely” work, ask them to put a percentage on it instead — the conversation that follows is almost always more honest than the original claim. And track calibration, not just outcomes. The real skill isn’t being right. It’s knowing how often your 80%-confident calls actually land 80% of the time — and that number is trainable, the same way accuracy alone isn’t.
Best for: Leaders who want a framework for making calls without perfect information, not a forecasting method. Reading commitment: About six hours, conversational and story-driven rather than academic.
That shift — from a single confident forecast to an honest range of possibilities — is exactly what a newer generation of planning tools is built around. One worth a look this month: Cube, an AI-powered planning platform that plugs directly into the spreadsheets a finance team already uses. Instead of a static plan built once and defended all year, it lets a team run several weighted scenarios side by side and update them as conditions change, without rebuilding the model from scratch each time a number moves.
It won’t make anyone a better forecaster on its own, and it’s still a finance tool at heart, not a substitute for honest calibration. But for leaders trying to plan in probabilities instead of false certainties, it’s a real shift in the right direction.
There’s also a chance to put your own thinking in front of a wider audience: this issue brings an exclusive feature placement in AP News, arranged through TEI’s media relationships. AP News carries global reach and real credibility, particularly with investors and partners paying attention to exactly the kind of judgment this issue is about. TEI’s team handles the interview, drafting, and placement end to end.
Interested? Talk to our team to learn more about this opportunity and discuss the details. Schedule a call through our Calendly, or simply reply to this email and we’ll be happy to assist.
Take with you: The next time someone on your team says they’re sure, what happens if you ask them to put a number on it?
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