Why You Should Stop Trying To Reframe Your Failures In Job Interviews

Talking openly about failure, instead of spinning it into a positive, can make for more honest hiring decisions.

Why You Should Stop Trying To Reframe Your Failures In Job Interviews
[Photo: Flickr user Samuel Mann]

We all cringe when we hear that clichéd job interview question: Tell me about your biggest weakness. Candidates learn to spin their answers (“Sometimes I’m just too passionate about working hard to make my employer succeed!”).


The impulse behind this question, though, isn’t misguided. You want to work with people who can reflect and learn from mistakes. So what’s another way to get at the same concept?

Kevin Gibbon, CEO and cofounder of Shyp, a startup that aims to make shipping easier), reports that he’s had success in interviews by asking people to tell him about a time they failed. “It’s not something that makes a lot of sense,” he says. “It seems like you’d want to be surrounded by people who’ve been really successful–who’ve been a part of something great.” But there are good reasons to probe this, and indeed, to be open to hiring people who’ve worked at all sorts of failed endeavors.

First, failures are interesting to talk about. Just look how many online headlines mention “mistakes.” We’re naturally drawn to click on such things, and “whatever you can do to open people up is good,” Gibbon says. “You get at what their real personality is.”

But beyond that, a failure presents the opportunity to ask “What did you learn from that, how are you better for it, and how will you do better next time?

Gibbon has his own answers for that. Before starting Shyp, he ran another startup that scored a reasonable number of customers, but not sufficient revenue. He learned several tough lessons that have helped him this time around.

First, it’s important “to really make the business work from day one.” Second, if you’re making money on every order, “you’re in control of your own destiny. If you don’t need to raise outside funding you don’t have to.” And finally, “another big one is being financially responsible.” There’s no need to have a huge building or fancy furniture. “I’ve had to shut the lights off,” he says. “I know exactly what that feels like,” and it generally feels like you don’t want to do it again.


Others who’ve turned off the lights likewise “have something to prove,” he says. “That drives a lot of people. They will do absolutely anything it takes to make this successful.”

To be sure, “it’s not going to be a no-go” if you don’t have a spectacular flame out on your resume, Gibbon says. Likewise, you need to learn from failure for it to be valuable. “Hopefully you won’t do the same thing over and over again.” But most of us haven’t succeeded wildly at everything in life.

There’s much to learn from talking about the moments that weren’t as awesome. Indeed, talking about them may increase the chances of awesome moments happening in the future.

About the author

Laura Vanderkam is the author of several time management and productivity books, including I Know How She Does It: How Successful Women Make the Most of Their Time (Portfolio, June 9, 2015), What the Most Successful People Do Before Breakfast (Portfolio, 2013), and 168 Hours: You Have More Time Than You Think (Portfolio, 2010). She blogs at