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

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.


Get more tips from our Interview Q&A series.

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Alexis Perrotta profile image

Alexis Perrotta

As the Associate Director of Marketing and Communications at Idealist and a lifelong nonprofit professional, Alexis offers job seekers, game changers, and do gooders actionable tips, career resources, and social-impact advice.

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