Tell Me About The Time You Failed

I’ve had more than my fair share of occasions to hire someone. I’ve done it on my own, and in teams of people. I’ve been the one making the decision, and I’ve been in an advisory capacity.

failure by Flickr user tinou bao
"failure" by Flickr user tinou bao

There’s a question I always ask, but that I myself have never been asked. Indeed, when I ask it, most colleagues seem to respond somewhere between rolling there eyes and looking at me in shock. But I think it’s one of the most important questions you can ask.

It’s this: “Tell me about a time that you, personally, failed.”

What I am listening for is the quality of being able to admit that I failed. In my experience, this is an incredibly rare quality. It is the building block for the kind of humility I want my colleagues to exhibit and that I want the initiatives I lead to exhibit.

I am looking for someone who actually has an answer to the question.

In fact, so few people actually answer the question as posed, that I have had to rethink my approach. I used to see the question as fundamental and not being able to answer it was a serious downcheck. Now I’ve flipped it around — not having a good answer is neutral, while having a decent answer (or any answer) is a big-time plus.

Failures Are Not Mistakes

Note that the question does not ask about a project that failed. That would elicit interesting information and reveal something important about how a candidate goes about understanding and organizing their work.

The question also does not ask about a “mistake.” We all make mistakes and they can be big and small. I am looking for a mistake that rises to the level that the person individually would call a failure. It may not have momentous consequences, but it needs to have significance.

This question is all about mindset.

I prefer to work with people who can admit they were wrong, because it makes it easier for me to admit when I am wrong. It’s so easy to see admission of failure as a sign of weakness. It’s what we’re taught from the beginning, especially when it comes to the workplace.

But people who behave that way are a drag. When they do fail, by not being able to own up to it, they create churn, resentment, and inefficiencies. Plus they seem to have bad karma that can just be a bummer to be around.

The Humility Of Organizations

But humility is an increasingly critical skill for organizations and their leaders to have, too. The last decade has seen the empowerment of the individual in ways no one could have imagined.  As organizations make missteps in this environment, they will have to apologize. For an object lesson, look at the difference between Domino’s Pizza (who addressed a problem head-on, with sincere remorse) and United Airlines (who stonewalled and tried a token donation to a nonprofit).

In this environment, to pretend that one is always right is no longer just ludicrous. It is a recipe for — well, for failure.

Everyone fails. I want the organizations, initiatives, and people I work with to be able to own up. This is the kind of weakness that makes everyone stronger.

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