Job Interviews: What’s the Biggest Challenge You Ever Had to Overcome?

One of my favorite interview questions to ask a job applicant is the one about overcoming a big challenge. It's interesting to see what you consider a major obstacle and how you talk about yourself as you share the story of what you've overcome.

For you, the job seeker, it's a wonderful chance to tell a personal story that plays up your strength and resilience. Just be careful … you don't want to turn it into a speech worthy of an Oscar! If you are prepping a response to this question for an upcoming interview, know that it's a good idea to continue applying for other jobs (just in case things don't work out after the interview). Write new resumes (or tailor an existing resume) for additional job applications using our Resume Builder.

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How to handle the biggest challenge interview question

This question is a chance to show an employer how, when faced with tough times, you turn to your inner strength and innate skills to find solutions. As with all answers to interview questions, it's important to be thinking about how this helps paint a picture of someone they want to hire … and not just someone who has had a lot of bad stuff happen and survived.

Keys to answering the question:

• If at all possible, look for work-related things that presented huge challenges and for which you were able to find solutions.
• Ideally, you want to think of things that relate to the needs of this job in some way. For example, if the job requires you to work with customers, think back to a time you did a great job handling someone who was especially tough to deal with. Or if the employer wants someone who has good analytic skills, think back to a time when you came up with a solution to a huge problem others couldn't see.
• Include why you considered it such a big challenge, so it doesn't look like you are skirting their real question.
• If you are just out of school and want to use things like an athletic accomplishment or project you spearheaded, those are great.
• Stay away from purely personal stories (such as having an illness or a dysfunctional home you overcame) unless they point directly to the job in some way.
• Tell the story naturally and keep it to a few minutes at most. It shouldn't be too long or dramatic. Just a picture of what you are like at your best under tough circumstances – and how that benefited your employer or teammates.

Be careful when talking about personal obstacles

We all have things in our past that we've had to overcome and this question can lead you right down that path. But I think you need to be careful about making your stories about overcoming pain and suffering the focus of your interview.

To be clear, having survived tough times is certainly something you can be proud of. It's just not necessarily the story you want to leave the employer with as part of your interview. Unless it fits the job.

As an example, I have a friend who had polio as a child. She's been on crutches all her life and overcome many obstacles related to that challenge. But in interviews, she doesn't make that her story. She talks about things like the time all the computer systems went down, and she still met her client's deadline. Or the time a major client threatened to leave the agency, something that could have sunk them, and she figured out a way to get her to stay. Or the time she overcame intense fear about speaking in public and participated successfully in a marketing forum panel.

They already knew she was on crutches. But she took this opportunity to help them know she's more than that … she's a determined problem solver. If it had been a job working for an organization that helps physically challenged people, then she would have told her "overcoming the obstacles of having polio" story. Otherwise, she was wise to focus on selling what the employer needs for the job.

People may admire gumption, but interviews are about finding marketable skills they want — and employees who are far more than their personal history.

Some final thoughts

This can be tricky, since the employer is asking you about your "biggest challenge" and what I am suggesting is that, if your biggest challenge is too personal, you should not go there. Instead find the biggest work obstacle or, if you don't have anything even close, something related to school, volunteer work, or personal projects.

Think about how they will remember you after the interview. Even if you've given less than a perfect "biggest challenge" answer, you are better off finding a story that leaves them with an impression that you are someone who will find solutions for them than the guy who survived a big storm.

And if they push you for something more personal (most employers won't) … remember you have a right not to reveal things related to health or details of your personal life. So just be prepared to explain why the story you told felt like a personal challenge and how what you learned has stayed with you. By then, they should be ready to move on.

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