The question you should have asked first

The most expensive decisions I have watched people make were not made by careless people. They were made by careful, intelligent people who ran a rigorous process on the wrong question.

That is the uncomfortable part. Intelligence is protection against arithmetic errors. It is very little protection against framing errors, and framing is where most decisions are actually lost.

The question underneath the question

Someone asks whether to raise a round. They build a model, compare terms, talk to three investors, and decide. The process is sound. But the question they should have been answering was whether the business needs capital at all, or whether it needs to stop doing two of the four things it currently does.

A good process applied to the wrong premise produces a confident wrong answer, and confidence is what makes it expensive. Nobody revisits a decision they felt sure about.

Three failures that look like analysis

Deciding at the wrong altitude

You can spend a week choosing between two hires and never ask whether the role should exist. The narrower question feels tractable, so it wins attention from the one that matters.