Two candidates, one role. One had led a function at a company you would recognize. The other had a scrappier resume, two years at a fifteen person company, no impressive titles. Most founders pick the first one every time. The credentials feel like proof. They are actually proof of something else.
A career built inside a big company trains a very specific skill. Wait for headcount before committing to a plan. Wait for budget before shipping something new. Wait for enough certainty that a decision cannot go wrong before making it. That is not a character flaw. It is what the job asked of them for years, and they got good at it.
A twenty person company asks for the opposite. Someone has to make a call with half the information they would like, today, because the customer call is in an hour and there is no one else to ask. The resume that looks the most impressive is often the resume of someone who has never had to do that.
This is why the hire with the shinier background sometimes struggles the most. Not because they are less capable, but because the environment that made them look strong on paper trained the opposite instinct from the one the job needs now. And it is why the hire who looks unfinished on paper, someone who has spent two years doing three jobs at once at a small company, often adapts faster. They have already been doing the actual job. They just have not been doing it somewhere with a recognizable name on the door.
Founders keep making this trade anyway. Not because they cannot see it. Because the resume is the fastest thing to evaluate when a role has been open for six weeks and the pressure to fill it is real. Mission fit and comfort with ambiguity do not show up in a document. They show up in a conversation, and a conversation takes longer to run than a resume takes to read. That conversation only works if it is built to draw this out. A generic interview will not show you how someone handles ambiguity on its own.
The fix is not to distrust every strong resume. Some of those candidates thrive at this stage too. The fix is to notice what you are actually screening for, on the resume and in the interview itself. A resume tells you what someone did do. It rarely tells you what they can do with less than they had.
Ask a different question before the next hire goes out the door. Not what have they led, but what have they done with nothing. Do not ask about ambiguity directly. Almost everyone will claim to be comfortable with it. Ask instead for a real moment when they had to decide without enough information, and what they actually did next. That is where the real differences show up, and it is the one that decides whether someone will make it here.