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Answers to “What Challenges Have You Overcome?”

By Biron Clark


In a job interview, you’re likely to be asked, “What challenges or obstacles have you overcome?” Or, “What is the biggest challenge you’ve overcome?” But what type of challenge should you describe? And do you need to pick a work example?

Coming up, I’ll share why employers ask interview questions about challenges and how to give a successful answer, with full answer examples.

Why Employers Ask You to Describe a Challenge You Have Overcome

Employers will ask you about an obstacle or challenge you’ve overcome, or for your biggest challenge, to make sure you’re comfortable handling adversity. They don’t want to hire people who have never been in a tough situation, or can’t provide an example of a time their life was difficult, because they’ll worry that you might panic and fold when the work gets tough for the first time. So telling them about a time you were successful in handling a challenge makes them feel like it’s lower-risk to hire you. And that’s important to employers.

Answering “What Challenges Have You Overcome?”

When you’re asked an interview question about a challenge you have overcome, you’ll likely have a few examples come to mind. You may think of work challenges, personal challenges, or school challenges. Yet, to give a clear and concise answer, I recommend you pick just one challenge. If you have prior work experience and can think of a job-related answer, then I recommend you do so. Employers will see a work situation as most relevant to their needs.

Yet, it’s possible to give great interview answers to this question by talking about a personal life challenge as well. So if you’re an entry-level job seeker or have one particular challenge that you feel you’re most proud of overcoming, then you can certainly share a personal story. While a personal life challenge may not be as relevant to the work you’ll do for a company, it can certainly make for an emotional, impressive story. And that means your situation/answer is more likely to be remembered by the interviewer. You can also ask the interviewer to clarify by saying, “Sure. Were you hoping to hear about a work challenge? Or a challenge from any part of life? A couple of examples come to mind so I thought to clarify before I answer.” No good interviewer will fault you for that. Just be ready to decide for yourself if they say, “Any challenge is fine.”

Watch: How to Answer “What is the Biggest Challenge You Have Overcome?”

How to Answer “What is the Biggest Challenge You Have Overcome?”

Employers may also ask for the biggest challenge or obstacle you’ve had to overcome. It’s normal/acceptable to give a personal answer here. Still, if you’ve faced a substantial challenge at work, then I recommend mentioning that. This will help ensure your response shows that you’d be successful in this new job. When answering interview questions about past challenges, it’s important to show traits that employers want, such as:

If you can mix a few of those traits into your answer, you’ll be more likely to get hired for this new job. However, if you feel that an answer from your personal life would be more compelling, you can share that. I’ll show an example of a personal answer and a job-related answer coming up soon, so keep reading.

Sample Interview Answers to “What Challenges Have You Overcome?”

Full Example 1:

One of the biggest work challenges I’ve overcome happened at my last job. Two team members were let go and I was left with the workload of three people. I fell behind and knew I couldn’t keep up in the long term, so I asked my manager for help. We came up with a solution that involved hiring, getting temporary help from another team, and streamlining our team’s processes to be more efficient, too. The experience taught me a lot in terms of communication and problem solving, and I think I’m even better prepared for the next problem or challenge I’ll face since I overcame that previous obstacle despite it feeling hopeless initially.

Full Example 2:

One of the greatest obstacles I’ve overcome was moving here to the United States when I was 10, without speaking the language fluently. I had to make new friends, learn the language, learn the culture, and adjust to a completely different way of life. One thing that made me successful was my natural curiosity and interest in learning. I’ve always been a good student, someone who reads and studies a lot, and someone who enjoys picking up new knowledge in general. I’ve taken that approach to learning new skills on the job, too, which I think has helped me get ahead in my personal and professional life and overcome obstacles or disadvantages.

Note that you can use the same type of answers above to describe the biggest challenge you’ve overcome if the hiring manager asks that instead. Also note that one example response above is a story about a work challenge, and one is a personal experience/problem. Find and choose the best example based on your background and the position you’re interviewing for. Both types of answers can be powerful and effective in the right scenario, if you overcame a challenge that shows the employer positive traits and life skills.

Obstacles Overcome: 15 Examples

To help you brainstorm more answer ideas for this question, here is a list of example obstacles you may have overcome:

1. Having to fix a coworker’s mistakes

Fixing the mistakes of another person at work could make for a great challenge you overcame. Maybe you were new in a role and asked to use your experience to redo the work of someone else. Or perhaps you had to step in to fix an emergency, such as an angry customer/client caused by the work of another person on your team. Or if you’re a recent graduate or still a student, maybe you had to fix a classmate’s work at the last minute on a group project. These all make good stories to tell, as you explain how you stayed calm and chose the right strategy to find a way out of the situation.

2. Having to hire one or more people in a short time

If you were a hiring manager under pressure to hire many employees in a short period, that’s also a great story to share, especially if your next job involves hiring/leading as well. Remember, the best answers to “tell me about a challenge you overcame” will demonstrate how you’ll be effective in this next job, too.

3. Filling in for a coworker who was fired

It can be tough on the entire team when a coworker quits, is fired, or is laid off. Showing how you dealt with an unexpectedly high workload by staying organized and handling the stress can make a good story.

4. Having to fire or lay off workers

If you’ve been in a leadership role and were asked to fire or lay off workers, that can be incredibly difficult emotionally and mentally. This makes a good story and experience to share, and is a chance to demonstrate your communication and management skills.

5. Learning a new skill or adjusting your skillset to stay effective in your role

If your skills became outdated or needed an update, and you took on the challenge, either through continuing education, online courses, or asking for more training/learning opportunities at work, then consider sharing this in your interview answer. This could be a good way to show that you’re proactive in handling obstacles and that you are career-focused and driven, too.

6. Being short on cash after a shift, if you were a cashier or in another cash-handling role

If you ever worked as a cashier or in another role handling money, it can be incredibly stressful and difficult to be missing cash and have to explain that to your employer. This happened to me in my first job, a part-time cashier role while I was a student. I won’t explain the details, but through a clever scam someone pulled on me, I was nearly $100 short at the end of my shift. Over time, I was able to recover and get back to being in good standing with my employer, and I learned a lot from the experience. If you’ve experienced similar, this is something you could tell the interviewer to demonstrate honesty, integrity, and the ability to bounce back from adversity.

7. Any difficult ethical decisions you’ve had to make

If you were put in a tough spot in terms of making an ethical decision at a past company, or as a student, feel free to share that. Just make sure it’s something that won’t give this interviewer doubts about your character now. Only share this type of story with an employer if you’re sure it demonstrates that you’re ethical and honest, and did the right thing.

8. Resolving problems/disputes between coworkers

If you were working with two or more people who had a dispute and you helped solve it, this can be a great story to share… especially if this disagreement was harming the employer, and if working out the dispute helped the company.

9. Repeatedly clashing with a team member, or dealing with a team member who was difficult to work with

If you were stuck with a difficult person on your team and had to find ways to work with them, this can be something worth sharing to demonstrate how you’re able to communicate and problem-solve in your career.

10. Planning a complex event

Whether in your career, studies, or personal life, if you’ve planned out an important and complex event and faced challenges along the way, this can certainly make for a good story to share in the interview. You can demonstrate skills like organization, handling pressure and deadlines, working and coordinating with many different people on a project, etc.

11. Preparing for an important speech or presentation

Having to prepare a detailed speech or presentation in the past would also make a good obstacle to talk about in your job interview. For example, if you had never spoken in front of a large crowd before and had to give an important presentation under short notice, use that example to show employers how you prepared, how you practiced, and how you enjoy building new skills (the new skill in this case would be public speaking).

12. Dealing with an angry customer or client

Resolving an issue with an angry or abusive customer can be a challenge. If you faced this obstacle and were able to keep going, stay calm and polite, and resolve the issue, then this story would demonstrate many traits that employers want to see.

13. Losing data or work related to a project and having to redo it under a tight deadline

If you’ve ever worked on a project and lost some or all of the data with limited time to redo it, this could make for a fantastic story to tell the interviewer. Just make sure you’re sharing a story with a positive outcome, where you overcame the obstacle.

14. A difficult deadline you faced

If you’ve faced a challenging or seemingly impossible deadline, and somehow delivered the work on time, then this is going to be an impressive story to share.

15. Being asked to learn a new skill or step into a new area in your team or company

Sometimes, your employer will ask you to learn skills or step into a completely new area when you didn’t want or expect to. If you’ve done something like this successfully, it can make a great response to any questions about a work-related challenge you’ve faced. This type of transition can be difficult in terms of learning the skills, but also mentally/emotionally. And so discussing these things will demonstrate many positive traits that employers want and need.

Keep Your Answer to 60 Seconds or Less

Aim to keep your interview answer below 60 seconds. Practice at home by recording your answer on your smartphone if you need to verify the time. This guideline will keep you from sharing too much info or telling too long a story. This may also help you in deciding which example of an obstacle to share. If you’ve overcome a few obstacles and feel one situation would be difficult to describe in a minute, and the other would be better suited for this length of answer, then choose that. There’s a benefit to giving a clear, concise answer here, in terms of impressing the hiring manager. So pick a story that you can tell clearly and relatively quickly. This doesn’t mean you should rush your answer. Make sure to explain the situation clearly without skipping any important details. Just be aware of the time, since most hiring managers aren’t looking for answers that take a few minutes each. That makes the overall interview take too long.

Use the STAR Method to Keep Your Answer Organized

To keep your interview answer clear and brief when asked about a challenge you overcame, I recommend using the STAR method, which is short for:

  • Situation
  • Task
  • Action
  • Result

This is how I recommend answering all sorts of behavioral questions (questions that begin with a phrase like “tell me about a time…”) Start with the overall situation you were in (were you working a job? studying? etc.) Next, describe the task at hand and the challenge you were confronted with. Then share the action you took to tackle the problem or obstacle. And explain why you took that action. Finally, describe the result, which should be a positive outcome, and possibly a lesson learned to better handle future situations. Always tell a story with a positive outcome. This will do a better job of impressing the hiring manager in response to any behavioral question.

Conclusion: How to Describe an Obstacle or Challenge You’ve Overcome

Next time you’re faced with an interview question like, “Describe a challenge you have overcome,” remember the tips above. Pick one specific example, always tell a story with a positive outcome and/or positive lesson learned, and keep your answer to this question brief (around one minute). If you do this, you’ll be one step closer to landing the job. And if you’re not sure whether the interviewer wants you to tell an example from your personal life or work life, ask. It’s better to clarify an interview question before answering than to give a less-than-ideal answer because you didn’t understand what the other person wanted. So take your time to understand the question first, ensure you know what the interviewer wants, and then share a significant challenge you overcame and how.

Biron Clark

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