Tough Interview Questions - What is your greatest failure?

Following is a tough interview question:

What is your greatest failure?

Similar interview questions:
What is the greatest disappointment of your career? Tell me about a time when you let down your boss or your team. What is your greatest regret?

Why the interviewer is asking this question:
The interviewer is putting you on the spot to identify a failure in your career or life. This is similar to the "What is your greatest weakness?" question, but it focuses on the results and outcomes rather than a behavioral trait. It is one of the most difficult interview questions to answer and isn't asked very often, so most candidates are not prepared for it properly. Often, candidates answer this question with their pre-planned "greatest weakness" answer, but that's not the question and a practiced interviewer will come back to the question and ask specifically about the results. Overall, the interviewer is trying to identify whether you are self-aware, so first and foremost is whether you have the ability to identify a failure or shortcoming in your career and/or life. The second aspect is whether you have taken the necessary steps to avoid this type of failure in the future. We all make mistakes. Yet few actually learn from their mistakes to avoid repeating them in the future. That's what the interviewer is seeking.

The best approach to answering this question:
Spend time thinking about what are truly your greatest failures in your career and your life. That does not mean you will reveal the greatest one to the interviewer, but do take time to review in advance. If there is a failure that is too personal (a common wrong response is to talk about a failed marriage that ended in divorce), avoid it in the interview. But think about your failures in advance so that you can identify one that: a) is not too personal; b) you can openly discuss how and why it happened without reflecting negatively on you as a candidate; c) you have remedied from occurring again in the future. The best examples are failure in your career or career preparation, such as your education. If you have a life story that ties back directly to your career, it can be used, just make sure it is not too personal.

An example of how to best answer this question:
[after 3-5 second pause thinking about your response] "As I look back on my career, probably my biggest failure or regret has been that I didn't prepare myself better in my education. I took a lot of coursework in college which really didn't contribute to my career, when I could have and should have been taking additional courses in my major. I knew this was a shortcoming early in my career when I was faced with work circumstances for which I simply had not fully prepared academically. I eventually remedied this by going back to complete my MBA. However, I know that the first three years of my career after college would have been much more productive if I had spent more time during my undergrad career focused on upper level courses in my major rather than taking electives."

An example of how you should not answer this question:
"Probably my biggest failure in life has been my first and second marriage and the resulting divorces. While I've had a successful career, my personal life hasn't been as successful. I made bad choices in selecting a spouse that came back to haunt me in both cases. Both of my spouses were pretty crazy, wow, could I tell you some stories. But I'm over that now and ready to move on."

Remember to answer each interview question behaviorally, whether it is a behavioral question or not. The easiest way to do this is to use an example from your background and experience. Then use the S-T-A-R approach to make the answer a STAR: talk about a Situation or Task (S-T), the Action you took (A) and the Results achieved (R). This is what makes your interview answer uniquely yours and will make your answer a star!