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

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.

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  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.

Matt Hunt has spent the better part of the last decade leading innovation for a Fortune 50 retailer and is now a professional writer, speaker, consultant, and founder of Stanford and Griggs, LLC. With more than 20 years of business and technology experience, he has demonstrated excellence in business strategy, innovation, and leadership development with large companies, small companies, and nonprofit organizations. Follow Matt on his blog,, or connect with him on Twitter, Google+, and LinkedIn.


16 Comments on “The Magic Interview Question: Have You Failed in Your Career?

  1. 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…



  2. 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,


  3. Matt,

    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,

  4. 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.

  5. 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.

  6. 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,


  7. 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.

  8. Natalie,

    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,


  9. I’m not making it. 22 years as a drafter designer and I ended up working for a sole proprietor that creates his own rules. No sooner did I become a mere hourly slave to a shit salary, than I was also asked to cover the desktop support and IT functions at the company since our original admin moved up north… I haven’t been able to parlay this into an increase in pay, because the business owner either feigns ignorance of its value, or expects employees to validate and justify a higher salary, in order to give him the opportunity to refute. There are never any “reviews”, there is no HR dept, and so, in all honesty a person begins to see no way out other than some permanent action…

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