Thanks starting this thread.
I am not telling about the toughest question faced by me, but a real incident which happened last day.
I conduct interview for many firms as an outsider. On one of such interviews, which was on last thursday, (20.08.09) I asked a boy ( he was not very smart, but good, completed his graduation and had a good look ) that what is his career goal.
I don't know what was wrong with my question, but all of a sudden he took my hand a give a loud weep in the midst of weep, he said, he don't have anything like that. Then I asked him very softly, whether he understood my question he said yes.
Then I talked to the boy outside, came to know about his problem. Though not selected for the specific firm, I have given him some courage from my side. From that day to till, he is calling me on a regular basis, and saying about the progress he is having.
It was rather tough for me because a person sitting in front of me was crying. But now, I am very happy that I can atleast help me in setting a career goal.