How to Answer “Tell Me About a Time You Failed”

"Tell me about a time you failed" is no one's favorite interview question. Understanding what the interviewer is really asking, choosing the perfect example, and having a template will set you up for success.

Rachel Cooke
4-minute read
Episode #600
The Quick And Dirty

Answering the dreaded "tell me about a time you failed" during a job interview can result in a win if you're prepared.

  • Understand what the interviewer is really asking
  • Choose the right example
  • Focus on a failed outcome, not a failure to perform
  • Tell a story that hits all of the essentials

You polished your resume, pounded the pavement, and landed the coveted job interview. Congratulations! Now it’s time to prepare and rehearse.

You can never anticipate exactly what an interviewer will ask. But the window just before a job interview presents you with an opportunity to reflect on your career to date—your highs and your lows. An honest reflection will leave you with a handful of stories and examples in your back pocket that can lend themselves as answers to commonly asked questions.

Likely (hopefully), you’ll get a few softball questions. The interviewer may want to know how you chose the college you attended or what you loved most about your last job.

And also, chances are the interviewer will also hit you with a few whammies. And one of the "whammiest" of all is the infamous “Tell me about a time you failed”, or some variation on that theme.

Oh, joy. Because don’t we all love reliving—and describing for others—our lowest moments?

No one loves this question. Do you toss out a humblebrag ("I care too much and I work too hard!")? Or do you throw yourself under the bus ("I didn’t plan or organize well")? No. And no. But how do you find a safe space between those two poles?

The key is understanding what the interviewer is actually asking.

As a recovering HR person myself, this is a thing I know a bit about. So if you’d like to successfully show this question who’s boss, read on.

Understand what the interviewer is actually asking

If you’re wondering whether the interviewer is a sadist who enjoys watching you relive a painful moment, likely the answer is no. There are good reasons why your answer to this question can be incredibly telling. So, let’s start there. When the interviewer asks this question, what are they really hoping to learn?

Generally speaking, this:

  • Do you have humility?
  • Are you comfortable with the idea of failure?
  • Are you reflective of your own failures?
  • Do you take accountability?
  • Do you receive and take action on feedback?
  • Have you learned something from the experience?

Understanding that these are the unasked questions, your job now is to choose the right example and use it to tell the story in a way that delivers on all of the above.

Choose the right example

Choosing the right example means following a few simple guidelines.

  • The story should be about an actual failure. Don't hide behind some version of “I just cared too darn much” or “I worked too hard.” Someone who can’t come up with a single true failure is either lying, not paying attention, or playing it way too safe.
  • Show ownership. Your story shouldn't be a veiled attempt to blame someone else. Others may have been involved, but an example that shows your own humility is essential.
  • Focus on a failed outcome, not your failed performance. Your example shouldn’t show that you were sloppy or careless; it should show that you planned for an  outcome but didn’t stick the landing.
  • Demonstrate that you can learn from mistakes. Choose an experience that prompted feedback, which you’ve received, processed, and took action on.

A sample answer to “tell me about a time you failed”  

With your example locked and loaded, let’s talk about how you communicate this story in a way that hits all the right notes.

There’s no harm in beginning with a touch of levity. Kicking off with a brief comment like “Ah yes, personal failures—everyone’s favorite topic!” is a great way to demonstrate that failure is something you’re comfortable with experiencing and willing to learn from. It doesn’t make you sweat or panic; you can still be easy breezy.

From there, take a beat of reflection. You may be prepared with a story, but you don’t want the interviewer thinking you’re working off a script. Give yourself a moment, and use the pause to ready yourself.

Now it’s time to tell the facts of what happened. Humility, accountability, and failure of outcome versus performance all come into play here. An example might be this:

Early in my career, I was asked to lead a meeting with the department head to secure funding for a project. I was so nervous. I researched, prepared slides, and scripted talking points that I rehearsed so many times I could recite them in my sleep. We finally got to the meeting and I kicked it off with confidence, but within minutes it was evident the department head didn’t want my prepared script. She wanted to have a conversation with me. But I was so wedded to my lines that I couldn’t answer her questions. Ultimately we didn’t get the funding.

After the meeting, I was devasted. My boss gave me some feedback about the importance of preparing a point of view, but also of anticipating questions and being flexible, ready to listen and respond—even if my response is only that I’d have to do some research and follow up. It was a great lesson, and the experience has really influenced the way I prepare for meetings today. I’m eternally grateful to my boss for the feedback.

OK. Let’s consider that a complete response to the interviewer’s question. What did this approach serve to do for you?

  • It was authentic. The failure was real. You didn’t get the funding.
  • It showed accountability—you didn’t blame your boss for not preparing you. You owned the outcome.
  • It was a failed outcome (you didn’t get the funding) but not due to your carelessness.
  • It shows your gratitude for feedback—that you can receive it, process it, and adjust the way you work as a result.

I hope the approach I’ve outlined has taken some of the fear out of the most dreaded interview question. Simply follow this template and you’re likely to find yourself both pain-free and possibly in possession of a new job.


About the Author

Rachel Cooke

Rachel Cooke is a leadership and workplace expert who holds her M.A. in Organizational Psychology from Columbia University. Founder of Lead Above Noise, she has been named a top 100 Leadership Speaker by Inc. Magazine and has been featured in Fast Company, The Huffington Post, and many more.