Failing Without Fear: Embracing Failure and Honesty in the Search for a Job


Probably one of the most commonly asked questions in any interview process has to do with failure. These questions are incredibly uncomfortable – and we know that those doing the asking are trying to understand us at our worst. In my last blog post, I mentioned the idea of bringing your entire self to work. Let me ask you this question, do you bring your entire self to a job interview? The likely answer is no. And why is that? Because we’ve been trained to believe that showing failure or weakness in a job interview is career-limiting. But let me take a few moments to tell you why I think the opposite is true: being honest about your failings can lead to a better interview and a better job.

While most interviewers are not quite so blunt as to ask about our failings directly, the questions most interviewers ask arise in the form of, “Tell me about a challenge you’ve faced at work, and how you overcame it,” or what “are your weaknesses, or areas you would like to grow your skills.” The scripted response for these questions often ends up being one of two things. One, a ‘weakness’ you disguise as an asset. For instance, I tend to take too much work, because I like to push myself and work hard. Or a challenging situation at work being a “wonderful learning experience.” I honestly gag at these questions, and inwardly gag at myself at the awful answers that come out of my own mouth.

But could you imagine what it would be like if we were truly honest and told people our number one, “I messed stuff up big-time” failure? After all, these questions are designed to get someone to show their true colors – wouldn’t you rather find this out in an interview than a month into working with someone?

I did an exercise like this once when I was in a leadership development program at Deloitte. It was one of the first days of my cohort and the question was simple. What was your biggest failure? We were specifically told not to couch it in terms of “oh it was a great lesson learned,” or “it ended up being a wonderful learning opportunity.”

I still remember a partner who participated telling us that his biggest failure was when his client went live with a very public website (no, it wasn’t healthcare.gov, but similar) and the site was so overwhelmed with traffic it crashed… and was plastered all over the news. It was one of his first times leading a big project and he screwed it up royally. It was amazing to see a leader (and one who is still with the company and has done very well), admit to such a degree of failure so openly and honestly. It led to a kind of openness among my cohort that I have never felt at work. We all shared our biggest regrets/screw-ups and came to realize that we were all human, we made mistakes, and that was that.

Imagine if, at work, we could be truly open with ourselves and our bosses. We could say things like, “I didn’t like a job because the work was boring and it didn’t pay enough,” or “I really dislike people who make their lack of planning my problem,” or “Man did I screw up a situation…” and not have to apologize for it by couching it in terms of lessons learned.

Think of the answer to the question, what is a weakness of yours? The answer to the above, for me, could still be that I often take on too much. But it isn’t necessarily out of a bad intention, or a desire to prove to others I can do it. It is really about proving to myself that I can still do what I used to be able to do. In working with a disability, I tend to remember who I was, and what I was once capable of doing. I take on too much, because I secretly wish I had that ability. I don’t want to say no to exciting job opportunities, or new assignments because I don’t want to admit to myself that I am not who I once was. I want to think I can still do all that is expected of me – and do it well. But it is scary to admit this shortcoming to myself and to others who I barely know. Yet,  that kind of honesty is worth sharing.

To be honest, answering questions with honesty goes against every bit of job-seeking advice that you see. But, when I think about how I am in the workplace honesty is a very big deal to me. I like to call things like it is, and if I fail at something, I don’t beat around the bush. I admit, apologize and try to do better. So why should I not demonstrate this within an interview?

It is because truly admitting failure and weakness is difficult and can have very real consequences. In government, especially, a small mistake can have large and legal consequences. A past paper I wrote about bringing in more innovation into government detailed how much could be done if government were just a *smidge more* open to failure. And smart failure – scientific exploration failure, if you will. Where you test a hypothesis, it is wrong, but in learning so, you move one step closer to success.

But how can we do this? I think to start, it takes courage. It takes courage to admit a failure, own up to it and accept the consequences, come what may. It takes a moral fiber that we are seeing less of today. It takes even more courage to be the boss of such a person and say, “Hey , it’s ok… we all make mistakes. The sun will rise again tomorrow.” But imagine if… and make it a challenge to yourself to do one honest thing at work every day.

For some fun reading on all types of professional failures, I urge you to check out the book “Failure: The Secret to Success,” and its accompanying blog.  There are lots of tidbits that tend to make you smile and nod along in agreement. 

Beth Schill is part of the GovLoop Featured Blogger program, where we feature blog posts by government voices from all across the country (and world!). To see more Featured Blogger posts, click here.

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Your article brings up some interesting ideas, true honesty at the interview. After reading it, I too, feel enticed by the concept-that would be refreshing!. However, an employer needs to also hear how that “big mess” turned into a success or if not a success, what action was taken afterward to correct the mistake. I want to hear honesty, but also solutions, even if they were in hindsight.