Tough Interview Question - What has been your biggest professional disappointment or letdown?

What has been your biggest professional disappointment or letdown?

Similar interview questions:
Where have you come up short in your career and how did you handle it?
Tell me about something in your career where you would like a do over.
How do you handle failure?
What would your boss or professor say about how you handled something that turned out poorly?

Why the interviewer is asking this question:
This question forces a candidate to discuss a negative and how it was handled. We all have had disappointments or letdowns, so there isn't a way to opt out of the question. The interviewer is looking for how you handled the situation and what you may have learned from the experience.

The best approach to answering this question:
Select something significant in your professional life where someone or something fell short of expectations and what you did to handle it, along with any professional learning you may have acquired in how you would approach the situation in the future. It should be a major disappointment or you may be challenged with: "Is that really your biggest professional disappointment?" And then you will have to answer the question a second time. Get it right the first time with one of (although not necessarily the) biggest disappointments in your career.

An example of how to best answer this question for experienced candidates:
"It was when one of my recent projects was shelved right before our launch date. Our entire team had put in a great deal of time and effort to delivering a top-notch project, but there was a change in the overall strategic direction that caused them to shelve our project. In retrospect, we should have been doing periodic check-ins with higher management during the development life cycle to make changes earlier to either redirect the project or get an earlier indicator that our project was going to be shelved…"

An example of how to best answer this question for entry level candidates:
"Clearly my biggest disappointment is that I was not given a full-time offer at the end of my internship this past summer. However, my manager explained to me that there were no full-time offers being made to interns due to a temporary hiring freeze. He also noted that if and when that freeze is lifted, I would be the first one to whom they would be making an offer. In retrospect, I chose the internship for the role and didn’t look as closely how things were going at a corporate earnings level. However, it has given me the opportunity to meet with other employers such as you…"

An example of how you should not answer this question:
"It was definitely when I got laid off. I was totally blindsided by the layoff, since I was all about staying heads down and not making any waves, just coming in and putting in my 40 each week. I had no idea I was in the crosshairs of HR, but my boss told me they list-managed this whole layoff thing and my job was viewed as being one that the company would not miss, so I guess people didn’t really understand what I did…"


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!


Further review: know the answers to these Fifty Standard Interview Questions to be fully prepared for your interview!

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