The fact is this question weeds out people who truly havent' done anything difficult or unable to communicate their achievements properly. If you have an impressive set of skill / strength, then it should be easy enough for you to pick one.
In my mind the question forces the candidate to show the interviewer his / her:
1) Communication skills (i.e, is this person going to tell me all their problems, or just the one major problem that he/she needs help with)
2) What they view as an accomplishment or challenge
3) How they handle challenges
4) Their ambition (i.e, did they take a leadership position in their accomplishment or did they sit back and let everyone lead the project)