When I spoke with Lyla Perrodin, VP and CIO for Midwest Research Institute in Kansas City, she told me she likes to ask job candidates, "What's the biggest failure you've ever been associated with."
It's hard enough to get anyone to talk about their weaknesses, but getting someone to be honest and to think about their failures? When you ask them to talk about a project that was a failure, you can really get some insight into how honest are they, how thoughtful are they.
That came to mind while reading on the Microsoft JobsBlog about a job candidate who, after talking about his latest programming project, apparently was taken aback by then being asked, "What would you do differently next time?"
Chris Rosenau, who answered for Microsoft, said there's no "right" answer. Basically, the interviewer wants to know that you thought it through and that you learned something from the experience. Ditto for the question on failure and also when you're asked about your weaknesses.
In this Washington Post article, Rajul Pandya of the National Center for Atmospheric Research's internship program, is quoted saying:
I want to hire people who can say, 'I've thought about what I don't do so well and have taken action to do it better.'
Rosenau's advice: For every win or loss you're prepared to speak about, also be prepared to address how you would do it better given the chance.