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well this question gave me a hard time through my career of job searching
How long are you willing to fail at this job before you succeed? seriously when the employer ask me this it was like freezing or lost or seeing something that I have never seen before
One of the questions I ask my applicants during an interview that they seem to find difficult is "WHY SHOULD WE NOT HIRE YOU?". It is a tricky question that I usually use in overqualified applicants and when I'm on the verge of excitement from hearing too many positives and achievements coming from the applicant without any glimpse of any weaknesses coming from them. I want to know more about the other side of the applicant aside from what is written on the CV. This question will put him/her in a position where his/her confidence and humility will be put to the test. Regardless of their answer, I always give them a point for taking the risk and answering the question.
Another one would be, on the point where the interview is about to finish, I ask them "WHAT WOULD YOU HAVE DONE DIFFERENTLY IN THIS INTERVIEW?" This will be a surprise question to them and it will let you know whether they will give you that same confidence from the interview or they will state to you their regrets on their answers during the interview. Because in human nature, we all tend to think about the things that we have just said10-20 mins after we have said them (whether it may be on an argument or an interview)
WHAT YOU CAN DO FOR OUR COMPANY ? WHEN & HOW ?