Tell me about your long list of weaknesses, and I'll think you're a neurotic mess. Tell me you're flawless, and I'll think you're arrogant. But if you reveal one weakness, and it's the right one, then I'll begin to believe you're a leader.
So what's the right weakness? Here's an example from what I think is quite possibly the best job posting I've ever read:
The ideal candidate would love prototyping off of half-baked drawings scribbled on napkins in crayon. This is not going to be a good gig for someone who needs a proper spec or development process. The "products" are going to be research probes and will need to evolve with use. The end-goal is far more prototype than stable product and the goal will be to iterate quickly at the expense of stability.
The ideal candidate would be self-motivated and patient with an eclectic work environment. The work environment is a research lab and my management style is quite flexible (a.k.a. virtually non-existent). This is not going to work for someone who functions best through heavy management or direct intervention. Flexibility and patience are pretty critical and I expect a bunch of eye-rolling when I make crazy suggestions.
The author of this posting is Danah Boyd. Boyd works for Microsoft Research and Harvard's Berkman Center for Internet and Society, where she studies youth culture and social media. I love how she calls her own management style 'non-existent' and her drawings 'half-baked'. The communication is crystal clear -- we can imagine exactly the sort of person who would struggle working for Boyd, and we can picture the person who would thrive.
Think about the best leaders you have ever known. Are any of them perfect?
My suggestion: Like Danah Boyd, don't labor to present yourself as flawless, but instead be purposeful about which flaw you will own. When Boyd points out her own lack of managerial process, she simultaneously removes the power of pointing that out from someone else and reframes the conversation around a strength implied in the weakness. In her case, the absence of traditional management skills implies the presence of a free-wheeling culture of ideas that would be attractive to the sort of candidates she seeks for the position.
The right weakness is the one that is the flip side of your greatest strength. Tell me you tend to be a bit anal at times, and I want you to be my accountant. Tell me that you tend to be relentless in arguments, and I want you to be my lawyer. The best weaknesses are disarming.
Disarm, a verb, means 'to remove of a weapon' or 'to remove the activating device from a bomb.' As an adjective, disarming means 'capable of removing hostility, as by being charming.' It's the same concept -- in both cases, to disarm means to improve your position by preventing someone else from harming you.
The next time you feel the urge to shine a spotlight on your greatest strength, consider disarming your audience instead, with some purposeful candor about just the right weakness.