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The Magic Interview Question: Have You Failed in Your Career?

Matt Hunt
Mar 14, 2013, 5:55 am ET

Typical interview questions center on candidates’ successes. What have they done that makes them right for a position? What is their greatest strength? When have they succeeded?

These questions may aim to flesh out a skillset, work ethic, or propensity for learning. But, in reality, asking one magic question can actually provide you with much more information than any run-of-the-mill interview question ever could. The “failure” question not only gives you insight into a candidate’s work personality, but it also demonstrates her ability to keep your company relevant in the emerging information economy.

The Magic “Failure” Question

This vital question is actually a series of three. These questions should be asked toward the end of the interview, and only bring these into the conversation when a candidate has strong potential for landing the job.

  1. Tell me the last time you failed at something professionally. Everyone should have at least one failure they can recall. Most candidates will use this as an opportunity to externalize their failure as a result of someone or something that could not have been predicted. Pay attention to the way they identify the cause. Many are eager to describe what role others played in the failure, or how insurmountable the obstacles were. Look, instead, for candidates who accepted their part in a failure and turned it into something positive.
  2. What did you learn? This is arguably the most important part of the “failure” question. It provides insight into a candidate’s ability to turn failure into opportunity — and that’s vital for your company. For organizations to succeed today, we need more than just doers; we need thinkers who can use creativity and experimentation to build ideas and new models.
  3. Would you have done anything differently? The notion that people can be perfect in their vision and decision-making is dated and stuck within the management models of the industrial economy. The world of business is no longer linear. Disruptive technologies are being introduced so quickly that it’s no longer a question of, “Is your business flawed?” Rather, you should ask, “How long before your business becomes obsolete?” That’s why thinkers — people who are able to learn from failure and analyze the results of their actions — are so important. They’re able to understand their surroundings, identify their roles within the system, and think creatively to solve problems and improve processes.

Why Failure Is Important

Employees should be introspective enough to see the system and their own roles within it. As Daniel Pink noted in his 2006 book, “A Whole New Mind,” the thinking taught in schools and endorsed by businesses — linear, logical, and left-brained — was perfectly suited for the industrial economy, but not the information economy. Innovation has become king, and we need more than just industrial knowledge. We need right-brained creativity, empathy, and storytelling. To ensure your organization keeps innovating in this new age, use the “failure” question to find the following types of candidates:

  • Problem Solvers: The “failure” question shows whether or not a candidate has the intellectual capacity to break down and examine a problem. It’s crucial that everyone in the organization has this ability because waiting for others to solve our problems only creates bottlenecks.
  • Innovation Leaders: Most organizations can benefit from “new business” or “innovation development” teams that focus on long-term projects. But companies also need innovation to be a part of every person’s job responsibility. Everyone should be comfortable enough to “experiment” within roles, to occasionally fail at an idea, and share lessons learned.
  • Culture Evangelist: To stay relevant, your company has to be able to out-learn the competition. To make this a sustainable practice, you need your employees at every level to encourage risk-taking and to drive out the fears associated with failure.

Your organization’s culture will change as you begin to look for — and accept — failure in candidates from the start. New hires will find it easier to hit the ground running because they won’t be afraid to challenge assumptions or stretch their thinking, and they’ll begin to take calculated risks.

This article is provided for informational purposes only and is not intended to offer specific legal advice. You should consult your legal counsel regarding any threatened or pending litigation.

  1. Kola Crute

    Matt, this was a wonderful article about the ability to be a thinker. I find myself in the “think” tank quite often, revamping to change.

  2. Keith Halperin

    Thanks, Matt. “Innovation has become king, and we need more than just industrial knowledge. We need right-brained creativity, empathy, and storytelling.” I’ve been hearing this for pushing thirty years, and I’m still waiting to be hired for- or evaluated on a job based on these…I’m also thinking if my colleagues and I have EVER been asked how we’d innovate the hiring processes. This lack of grassroots recruiting innovation is particularly true in large technical companies…I’m willing to argue that the more a company talks about “innovation” the less the want the ordinary employee to try to innovate…



  3. Matt Hunt

    Thanks Kola, I’m glad you appreciate the article! I’d love to hear how your progress goes. -Matt

  4. Matt Hunt

    Keith, Thanks for your feedback. I can tell you that in the organizations that I have worked with this is a priority. They still need the right skills and proficiency but they are looking for thinkers and problem solvers. I will agree that this thinking hasn’t hit the tipping point yet but from what I am seeing it is gaining momentum.

    I do agree with you on the innovation point. Too many organizations are just talking about it but not putting the systems and processes in place to support employees who are working to drive innovation in their roles.

    Thanks again,


  5. HR Recruiter, Hiring Manager or Just Looking for a Job? Be Ready to Ask or Answer the Magic Interview Question. | Matt Hunt | Leadership, Innovation, & Failure

  6. Keith Halperin

    You’re very welcome, Matt. Anytime Stanford and Griggs, LLC’s clients are looking for some REAL recruiting-innovation advice, give me a holler.



  7. Gary Steeds


    A superior and very timely article. An open discussion about one’s failures and how they were handled would serve to answer many of those nagging and unanswered questions. Questions that pose themselves when considering “what kind of an employee am I bringing on board” How will they respond under the pressures of the failures of their projects within the functions of their position? Will it lead to innovation? Will they rise to the challenge and grow or the opposite?

    Will they share in what they learned or hide their failures denying the organization a “teaching moment” Our new digital environment and the speed of innovation demands that we not lose that knowledge.I wish that we could take fear and ego out of our work environment and create an atmosphere where we openly share in what we learned from our daily mistakes.

    Good job,

  8. Howard Adamsky

    Fascinating article. Matt is a writer for those who think and who question.

    Can you imagine never having failed? That might be the ultimate failure.

    Great work.

  9. Ty Chartwell

    Keith – agree w you.

    It’s the typical ‘lets stump the candidate questions’ that keep happening and by HR dogs who have never accomplished it themselves i.e., Tell me about a time you ran the 40 in 4.2, bench pressed 500lbs, pole vaulted 18 ft, climbed Mt. Everest, surfed the banzai pipeline, captured a stray alligator in the Keys, biked through the war torn zone of Syria, swam the English Channel. and sky-dived from 50,000 ft? What steps did you take, what was your process, what did you learn, how did you apply the learnings, what was the teachable moment, what mistakes did you not make that you thought you would make and the later made, what was your takeaway, how did you measure your success, with what best-practice tools did you use to measure success, what was your process in deciding what tools to use? The candidates i send in to interview at companies are shocked at the ignorance and arrogance of HR.

  10. Matt Hunt

    Thanks Gary – I appreciate the feedback! Since you appreciate the failure topic you might enjoy my blog on leadership, innovation, and failure:

    Thanks again,


  11. Matt Hunt

    Howard – thank you for the kind words!

    Much appreciated,


  12. Matt Hunt

    Ty – Thanks for the reality check. I agree with you that too many companies see the interview process as a mental labyrinth where only a few are supposed to survive and not as an opportunity to really get to know their candidates. To be honest this is why I like the failure question so much – it’s not about a right or wrong answer or doing mental gymnastics. It is about your own life experiences and being mindful of your failures.

    As for those employers with “HR dogs” I can only suggest that they reexamine their practices soon because as the economy improves and candidates begin getting multiple offers again they will be the one getting rejected.

    Thanks again,


  13. Workforce Development News – March 18, 2013 | Workforce Solutions Group | St. Louis Community College

    [...] The Magic Interview Question: Have You Failed in Your Career? [...]

  14. A great question to ask, especially for more senior level positions. | Makai Search Group

  15. Natalie Prigge

    Matt, what a powerful question to ask! I wonder how many candidates would actually be able to come up with an answer to this one on the fly.

    I would imagine on the most mature critical-thinkers and self-evaluators will be able to have an open discussion on this topic. After all, it means the individual has taken responsibility for his/her own failure, analyzed it, and learned from it. My guess is less than 10% of job seekers are at this professional level.

  16. Matt Hunt


    Thank you for your feedback! I agree with your suggestion that many candidates will not be comfortable answering the question. That is one reason why I find it so valuable. I’ve found that I can teach “thinkers” new skills but it is much more difficult to teach an employee to become self aware.

    Thanks again,


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