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

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.
   
• ...

Keep reading on Quick and Dirty Tips