What’s your greatest weakness?

So far this year I’ve had three job interviews. One the one hand, I’m being picky because I can afford to be–I’m not miserable, but I am growing increasingly more unhappy. On the other hand, I suck at interviews, and though I revel in the opportunity to compete for a position, I also loathe having to talk about myself because I feel that I talk too much and can’t strike a good balance between being humble and being cocky.

My first interview of the year was with a law firm; I first spoke with the staff recruiter, a meeting that I thought went very well, but when I met with the Marketing Director, I tripped over my tongue left and right and left the interview feeling pretty depressed about my chances. If I’d been offered the position, I obviously wouldn’t be writing this self-loathing bit of tripe, but I do take some comfort in knowing that I was one of two candidates out of 20+ who was seriously considered for the position.

My next two interviews were wastes of time, mostly because I learned during the interview that these were jobs I did not want. No big deal–it happens–but that doesn’t erase the fact that I blew chunks during the process. In fact, at the very beginning of one of these interviews, one gentleman asked me why he should hire me, and I couldn’t answer him. It’s not that I had no answer; it’s that I couldn’t organize my thoughts into a coherent and useful sentence. Instead, I just babbled.

I guess I’ve known for a lot of years that I don’t interview well, but I’ve never done anything about it. I just kept hoping that I would get lucky, as if my mouth were some kind of an appliance that sometimes works really well and other times does not. I need practice, and I finally realized that the best practice for me is to develop a script based on the interview questions, especially the toughest, that I’ve answered over the years. So for the last few weeks I’ve been developing a list that includes some traditional and some not-so-traditional interview questions. I’ve also been reading articles about preparing for interviews and have come across some interesting perspectives on interview questions. Take, for example, the following: What is your greatest weakness? Several authors have suggested, as you may expect, that the best approach this question is to “spin” your answer so that your weakness becomes a strength. Other authors suggest that you be honest and describe your weakness as a weakness but spin your answer by illustrating what you’ve learned and the steps you’ve taken to correct your weakness. I think I prefer that approach. So as I sit here and write about my greatest weakness, I’d like to ask you a question: what is the toughest (or best/worst) interview question you’ve ever been asked?