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James Sargent
James Sargent

Posted on • Originally published at open.substack.com

AI Makes Bad Decisions Look Reasonable

Most bad decisions don’t look bad at first.

They look complete. Confident. Well-structured.

That’s part of the problem.

AI is very good at producing outputs that feel finished. It fills in gaps, smooths edges, and presents answers that sound plausible. When you look at the result, there’s nothing obviously wrong with it. No red flags. No clear failure.

I ran into this while building TrekCrumbs. AI kept offering solutions that were technically sound. Add a layer here. Map fields there. Patch the edge cases. Each change made sense on its own. Nothing broke. Progress continued.

But those “reasonable” decisions quietly locked in assumptions.

Tradeoffs were made quietly. Defaults became structure. Nothing broke; the system just became harder to understand.

That’s what makes this dangerous.

When decisions aren’t explicit, AI doesn’t expose the problem; it hides it. The system works long enough for ambiguity to become expensive. By the time the cost shows up, it doesn’t look like a bad decision. It looks like friction, rework, and discomfort.

AI didn’t create bad decisions.

It made them easier to overlook.

Leadership takeaway

When decisions aren’t made explicit, AI outputs can feel correct while quietly locking in unexamined assumptions.

Action cues

  • Notice decisions that feel “reasonable” but are hard to explain
  • Pay attention to tradeoffs no one can clearly name
  • Watch confidence replace clarity in reviews

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