Interview Q&A | “What Has Been Your Biggest Challenge?”

woman thinking

Your goal in answering this question shouldn’t be to elicit the empathy of your interviewer. Although the question clearly asks for your biggest challenge, the interviewer doesn’t want to know about all of the professional obstacles you have encountered over the years. They want to know how you met and overcame those obstacles.

Many interviewers will tack on “… and how did you handle that challenge?” at the end of this particular question. However, even if they only ask you for the challenge, remember to stay laser-focused on how you developed and implemented a solution, too.

Discussing the right challenge

As you’re preparing for your interview, use these characteristics to identify the right story to include in your response to the question:

  • It should be easy for the interviewer to draw a parallel between the story you’re telling and the problem-solving skills you’d need for the job in question.
  • The challenge should cast you in a positive light. Try to identify a challenge in which you played the role of a leader, organizer, motivator, or problem solver.
  • Make sure it is actually a real challenge, and not just a story you pulled together to make you sound like a hero, but lacks in substance.
  • Of course, find a challenge that you successfully addressed!

It’s important to rehearse your answer for this question as you’ll want to be sure that your story doesn’t run on for longer than it needs to. Try to hit all of the important points in two or three minutes.

Pro Tip: Don’t select a challenge that is related to your working relationship with colleagues or supervisors. You will likely have an opportunity to speak to a challenging relationship later in the interview, but this is not that moment.

Crafting your response

Here is one example of how you could answer the “What has been your biggest challenge?” question.

“At my current job, I was tasked with setting up a new email marketing platform. This included learning how to use the platform, migrating data and content from the old platform, and training staff.

Once I completed my research and selected the best tool for our needs, the biggest lift was making sure to communicate the change to colleagues as far in advance as possible, and to remain available to respond to any questions or confusion. This was particularly difficult since employees at my current organization are highly averse to new technology.

I was able to develop a communication calendar, training materials and sessions, and follow-up guidance. This helped me to get the buy-in that I needed from stakeholders in the organization and I believe that my commitment to being available for questions put my colleagues at ease and made the process much easier.”

Pro Tip: As long as you’re not harping on your mistakes, it’s okay to also mention how you would handle the situation a bit differently if you had the opportunity.


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    • Chris
    • May 12, 2018

    Should personal adversities, if they are your greatest challenge, be mentioned?

    If one was, while homeless, in a car accident which caused life-long disability but has since been able to recover to the point where one is looking for a job that helps to make a positive social impact is that appropriate to mention in an interview?

      • Alexis Perrotta
      • July 9, 2018

      Hi Chris, great question. If personal adversity is a part of your story, I’d certainly consider alluding to it during your interview, but I wouldn’t suggest making it the focus. It’s important to remember that it doesn’t always make sense for a potential employer to learn about something so deeply personal before they have an opportunity to know you on a professional level, and furthermore, they may not process the information that you’re sharing in the way you had hoped. If your story of adversity adds context to one of your interview responses, I think it’s OK to include. But if not, I’d suggest holding off until your interviewer has an opportunity to learn more about you as a professional.

    • Carolyn
    • November 29, 2018

    Thanks for this answer. I’m hoping I might get some help answering a question I always dislike. “Where do you see yourself in five years?” Am I supposed to say that I’ll still be working at that place? If not, what would be my reason for moving on? It feels like a trap.

      • Alexis Perrotta
      • December 5, 2018

      Hi Carolyn, thanks for your question! We’ll be sure to answer that in an upcoming edition of Interview Q&A 🙂

    • Susan
    • December 6, 2018

    In my former position, I worked for a revolving door firm, which piled the work of four former failed clerical workers onto one person, me. On my first day, I received a two foot high stack of incomplete work to accomplish, in addition to a heavy daily workload. After several weeks of working twelve hour days without breaks, I halved the stack, in addition to keeping up with a growing daily workload. I found that a few office “survivors” had shouldered similar hours for up to nine years without being paid for their overtime or missing breaks. In the last two weeks of the job, I clocked in and out accurately, instead of “volunteering” daily up to four unpaid hours per day (plus lunch hour). For this, I was terminated. How do I explain this, when asked by an interviewer, “why did you leave your former firm?”

      • Alexis Perrotta
      • December 6, 2018

      Hi Susan, thanks for your question. Wow … this sounds like a very challenging environment! I personally don’t believe that “don’t say anything bad about a former employer” is always 100% accurate, without exception.

      If you left your job because of an unhealthy workplace and withheld pay, it’s OK to say that. No need to get into the specifics, but here are the things that I would be sure to mention: 1). You were terminated because you attempted to continue your work while also addressing issues of withheld pay 2). You tried to adjust to the situation and find a solution, and 3). If this is the only time that you have been terminated, you should definitely mention that as well.

      Finally, I’d go into your next interview with references from other jobs in hand. Be sure to have a cadre of folks who will vouch for your hard work and professionalism ready to share with your interviewer. And if you found that you connected with any of your colleagues at the organization from which you were terminated, check in and see if any of them would be willing to be a reference for you as well. It could be helpful to have somebody else who is (or was) in that same problematic situation vouching for you.

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