For Tom Gimbel, CEO of LaSalle Network, hearing how a candidate describes their shortcomings is just as important as how they paint their expertise.
Gimbel says he's made offers to "hundreds and hundreds" of people during his 25 years in the hiring game.
Many of those hires are familiar with his favorite job-interview question: "Tell me a time that you really screwed something up, that either cost the company revenue or cost them money, and what you learned from it."
Gimbel's reasoning for posing the prompt is straightforward: "You find out if people are authentic. I mess up things every day, [and I'm] happy to share it with you. And if somebody can't do the same, then are they really being realistic with you on any of their answers?"
Gimbel prefers to save the question for the tail end of the interview as a barometer for whether the candidate was being self-aware and authentic for the entire conversation.
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He asks the question both to candidates who've already made a strong case to be hired, as well as those who are floundering.
"I come at it from two different perspectives," Gimbel says. "If I feel the candidate is the right fit, this will validate them. Or if I don't think they are, this is the life preserver they need to save the interview."
As he sees it, even if things aren't going well with a candidate, he'll "see if they're really humble in their answer here, and maybe it can sway me."
How to answer it (and what not to say)
That being said, he says the most memorable interactions are when candidates don't have an answer for him — but that's not a good thing, Gimbel says.
Mistakes are bound to happen when you're trying new things. So, if a candidate doesn't have an example of a mistake to share, it could mean they're fibbing about their experiences and don't want to share a mishap, or they haven't tried something outside of the box in their role.
Prepare for this question by choosing a mistake that's "big enough to show you've got the bumps and bruises of real experience, but small enough to convey you are generally highly competent," NYU management professor and author Suzy Welch previously told CNBC Make It.
Avoid anything too trivial ("I once ordered catering for the wrong day"), phony ("I worked too hard on that project") or risky ("I lost a key client"). Then, spend the majority of your answer discussing the aftermath of the mistake: how you owned up to it, what you learned and how you grew from it.
Gimbel agrees: At the end of the day, he wants to know that a candidate can be humble, self-reflective and learn from past mistakes.
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