Answering Behavioral Questions: Your Biggest Failure

Part of our continuing series on answering the most common (and trickiest) behavioral interview questions.

Tell Me About a Failure


What’s the toughest behavioral interview question of them all? For many, it’s this one: Tell me about a time you failed.

I’ve noticed that more and more recruiters and hiring managers are including this question in their standard behavioral interviews. Some recruiters will even tell you that this is the most important interview question to ask a candidate.

Obviously, you can’t afford to FAIL to answer this question well. However, my experience is that most candidates are terrible at answering the question.

Why is it so difficult? Typical behavioral questions are tricky enough — but this one asks specifically about a negative experience. Negative experiences are tough to talk about in job interviews because your focus is on trying to present yourself in the best possible light.

You want to be candid, but not TOO candid. How do you talk about failure without sabotaging your chance of landing a job offer?

NOTE: This is Lesson 10 from the Big Interview interview training system. Take a quick look here if you want to learn more about it.

Read on for advice on how to prepare for and answer these critical questions about failure.

What Are Behavioral Interview Questions?

Companies ask behavioral interview questions to learn more about your past job performance. According to studies tracking years of hiring and firing at companies around the world, behavioral interviewing is the most effective way to predict future job performance and pick the right candidates. It’s not perfect, but it’s the best technique that we currently have.

Behavioral interview questions tend to begin with “Tell me about a time…” or “Give me an example of…” Each question focuses on a desired competency area (a few examples: communication skills, time management, creativity).

Read our Behavioral Interview Questions 101 Guide for more.

Why Interviewers Ask About Failure

“It’s fine to celebrate success but it is more important to heed the lessons of failure.”

— Bill Gates

You might assume that hiring managers ask this question to torture candidates — to dig for any evidence of a flaw, any excuse to reject you. When you look at it this way, it’s no wonder that many candidates freeze up and have trouble coming up with a good example of a failure.

It may reassure you to know that hiring managers don’t expect you to be perfect. They know that everybody fails.

They ask this question to understand:

  • Are you someone who can learn from failure?
  • Are you self-aware enough to acknowledge failure and weakness?
  • Do you take smart risks?
  • How do you view success, failure, and risk in general?

After all, if you’ve never failed, then you’ve probably never succeeded on any significant level either. Prospective employers want to know: Do you know how to fail smart and learn from your mistakes?

The most common phrasing of the question is the simple, “Tell me about a time when you failed” or “Tell me about a failure.” There are some other variations on this theme as well:

  • What’s your greatest professional failure?
  • Tell me about a mistake that you made.
  • What was your biggest mistake and what did you learn from it?
  • Tell me about a decision that you regret.
  • What’s your greatest professional regret?

How NOT to Answer Behavioral Questions About Failure

The most common mistake is to NOT answer the question. I can understand why a candidate might freeze up if asked about failure. If you haven’t prepared to address this topic, it can be daunting to try to instantly think of a good example and then describe it in a diplomatic way that shows you are both honest and a smart hire.

Many candidates will um and uh for a while and finally say something like: “Well, I can’t think of any serious failures. I guess I’ve been fortunate to be pretty successful in most of my positions so far…”

That might seem like a safe way to answer. However, from the interviewer’s perspective, you’re not answering the question at all.

This non-answer will be interpreted in one (or more) of four ways:

  1. You think you are perfect and thus have no self-awareness or ability to grow.
  2. You’re hiding a history of tragic failures that you don’t want us to know about.
  3. You don’t hold yourself to a very high standard, so you never fail.
  4. You always play it safe and never take any risks or make any bold moves.

None of these interpretations are particularly flattering.

The other common way to screw up this question is to blurt out something without thinking it through. Some candidates get flustered and insert foot directly into the mouth. They share something that makes them look bad.

Inside Big Interview

Our complete training system for job interviews, we give you video lessons, sample answers, and an interactive practice tool for all of these different versions of “What is your greatest weakness?”
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Watch this brief video to learn a little more about Big Interview, and then take a quick look at the step-by-step system we’ve developed to get you ready for your interview.

How to Answer Behavioral Questions About Failure

I strongly recommend that every job candidate prepare an interview story about a failure. As I mentioned earlier, this question has become extremely common — I hear from my corporate clients that they find it very effective in separating the B.S. artists from the solid candidates.

It’s also a question that can really bite you if you screw it up. Maybe you’ll get lucky and your interviewers will stick to shiny, happy questions about your awesome teamwork skills. But isn’t it better to be prepared?

As usual, when it comes to preparing for behavioral questions, I encourage you to use the STAR format as a framework to prepare your failure story.

With the STAR framework, you simply write down a few bullet points for each of the key aspects of your story (Situation/Task, Approach, and Results). This method allows you to hit all of your key points while keeping your answer concise (this is very hard to do without focused preparation).

Note: Big Interview has step-by-step instructions for creating powerful STAR stories — and our Answer Builder tool will walk you through the process quickly and easily. Learn more.

How to Pick a Good Failure Story

Before you jump into the STAR format, you must choose the right example to talk about. It is very important to select a failure example that will serve you well in job interviews.

Everybody fails — in big and small ways. The tricky part is to craft a failure example that highlights your strengths and smarts.

Here are some guidelines for selecting the right example:

  1. Choose a real failure. You must answer the question. Don’t go with something like: “We only improved sales by 35%, but I wanted to do more, so I felt like a failure. I guess I’m just a perfectionist.” (insert a humblebrag shrug)
  2. Don’t raise red flags. At the same time, you don’t have to confess your deepest and darkest secrets. Don’t choose a failure that was the result of a serious personal mistake (totally forgot to attend the meeting) or character flaw (probably shouldn’t have called the client “Sweetcheeks”). A team failure can work well because you share responsibility with others (just make sure you acknowledge your role and don’t try to pass the buck completely)
  3. Focus on learning. Pick a story that ends with a compelling example of a lesson learned. Ideally, you should be able to point to applying your hard-won knowledge/skills successfully on a subsequent project. (Read our sample answers below for inspiration).

Sample Answer — “Tell Me About Your Biggest Professional Failure.”

The sample answer below uses the STAR format to tell a failure story. You’ll notice that this example is more scripted than your own STAR bullet points will be. We took this approach to try to illustrate how the answers might sound in an interview.

When preparing your own STAR stories, there’s no need to write full sentences with detailed transitions. You can just write down rough bullet points to create a framework — your delivery should be a little bit different each time.

S/T (Situation/Task)

This is the “backstory.” Provide an overview of the project or situation. Keep it concise and give only enough background for context.

Example Situation/Task Bullets

  • I would say that my biggest professional failure was in my current role as a project manager at ABC Consulting Corp.
  • Last year, our team failed to land a $2 million new project from one of our existing clients.
  • The project should have been ours, but we dropped the ball.

Why We Like Them

With a failure story, you want to get right to the point in the S/T  section. Give them the basic facts about the situation/task. The emphasis should be on the positive — the lessons learned, which you’ll cover later in the R section.

This candidate takes responsibility for the failure and doesn’t try to sugarcoat it or lead with defensiveness.

A (Approach)

— After you have given a brief background of what the failure was, it’s time to walk through a bit more detail about what happened and why.

Example Approach Bullets

  • I think the biggest issue was that the whole team took it for granted that the project would be ours. We had a good relationship with the client and we had just wrapped up a very successful project for them.
  • A team of us, led by the account manager, went to pitch. It was a solid pitch and we got great feedback.
  • But in retrospect, we didn’t go the extra mile to wow them. We didn’t push as hard as we should have. That opened up the opportunity for a competitor to put on a big show and steal the business.
  • At the same time, we failed to truly understand all of the client’s key concerns. They told us that price was the #1 consideration, so we focused on demonstrating cost-effectiveness.
  • Meanwhile, a new senior VP had come on board and I now realize that his priority was picking his own vendor and he saw us as his predecessor’s pick. As the person working with the client team day today, I should have picked up on that and found a way to address it.

Why We Like Them

  • This is a pretty insightful breakdown of what happened. There is enough detail to allow for a full understanding of the outcome, but the candidate doesn’t go off on tangents or overwhelm with information.
  • The candidate has clearly thought about the causes of the failure and analyzed his own role.
  • He takes responsibility and identifies how both he and the overall team could have done better.
  • He doesn’t raise red flags about his work ethic or professionalism.

R (Results)

A good STAR interview story always features a happy ending. With a failure story, your R section will be a little different than usual. With a typical STAR answer, the R describes the positive outcome(s) of the actions that you took (increased sales, reduced costs, winning presentation).

With a failure story, the happy ending is a twist ending. By definition, failure is not a positive outcome. The positive outcome comes later and focuses on learning a lesson and becoming smarter/better/stronger.

Example Results Bullets

    • Losing the business was a real blow to the company — financially and from a moral perspective too.
    • I actually volunteered to lead the analysis of what happened and see what we could learn.
    • Our #1 lesson as a team was to never take a client for granted — and to never, ever settle for a “good-enough” pitch. We have to hit all of our presentations out of the park. And I can honestly say that we’ve done so ever since — and it has led to a record year for new business in our group.

Personally, I learned that I need to pay more attention to the dynamics within the client organization and read between the lines more.

  • As the project manager, sales aren’t the main focus of my job. However, as daily contact with the client organization, there is a lot that I can do to help the company bring in new business.
  • I decided to take a sales course to develop my skills and have found that I now really enjoy being closely involved in the business development process — and I am pretty good at it.
  • In fact, I made a point of staying in touch with my client contact from the lost project and continued to nurture that relationship.
  • As a result, when that contact moved to a competitor, she ultimately brought ABC in for an even bigger project than the one we lost.

Why We Like Them

The candidate analyzes what went wrong and what he learned from the experience. He looks at it from the organizational, team, and individual perspectives.

He demonstrates that his lessons were well learned by discussing the success of subsequent sales pitches.

He takes responsibility without seeming negative or defensive

He puts more focus on the R (what was learned) than on the failure.

Don’t Forget to Practice

If you’re a regular reader, you know how much we emphasize practice. Interview practice may not be exciting, but it is incredibly effective. I have seen the difference that practice had made for thousands of job seekers,  especially when it comes to answering difficult behavioral questions (including questions about failures).

The truth is undeniable: candidates who prepare and practice land more job offers. To paraphrase the old saying: Don’t fail to prepare, prepare to discuss your failure.

Please share your own experiences with interview questions about failure.

Bonus: Here’s a famous scene from Cool Hand Luke where a “failure to communicate” is described. Not sure if boss-man is following the S.T.A.R. format though.

(Main Image: Fair Use Parody. All trademarks belong to their respective copyright holders.)


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