Easy one to answer. Here are a few ways of getting by: Real Story: blah blah blah...blah blah...tada! Wow, great story, but boring. Fake Story: don't go overboard...base it around a real story and bend the facts gently. When i was asked this...i talked about my mission trip to Costa Rica (which i actually did)...but the obstacle i overcame was fake...i said that most of the other people on the team were sick when we were supposed to teach classes at an elementary school, so i took the initiative to organize a way to get past the challenge with those that were healthy...all said and done, it went well...haha, if it really happened it might of. I got a call back sayin that i had a job, but i already committed to another one which i quit later that month . Humorous Story: Just make them laugh...most of the time they really don't give a damn about what you're sayin...why not make it interesting. Oh, and if you're interviewing for a "dirty job"...just say that "it was really hard to get a regular sized condom to fit on my huge obstacle, so i decided to go with GLAD industrial strength, thus overcoming my problem." I actually used that once...but it was for a grocery store. i didn't get a call back, though i did get a smirk outta the guy. Ah, thehellwiththat, i really didn't want that job anyways. Sarcasm: just answer..."i have never overcome an obstacle, dumbass. that is why i'm applyin for a job at this damn grocery store instead of getting a real job." Question with Question: answer...how about you? have you ever overcome an obstacle?...this shows who is boss in this interview process. make him your b****. if it's a woman, *see humorous story*. I dunno...there's probably another hundred million techniques. The thing is...this type of question you should definately be prepared for.