How to Answer ‘Tell Me About an Obstacle You Overcame’

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Job interviews are one of the most challenging and nerve-wracking experiences we have to go through in our adult life. They can be stressful and uncomfortable, yet are necessary in order to secure a job and keep your head above water.

You have tough questions flying at you left, right and center and can find yourself stumbling, trying to answer them. The key to smashing an interview and coming across cool and collected is all in the preparation.

In this detailed guide, you’ll learn how to answer the tricky question ‘Tell me about a time when you faced a major obstacle at work’ to impress your interviewer and leave a lasting impression.



The Purpose

It’s often baffling when interviewers ask certain questions, but there’s a perfectly good explanation for ‘tell me about a time you faced a major obstacle at work’. This question is designed to help the interviewer discover what type of problem solver you are.

They want to know that they are hiring someone who has the ability to think on their feet and can demonstrate resilience in the face of a challenge. It’s your chance to show that in tough times you turn to your inner strength and possess skills to find quick solutions. "Throughout the interview, keep in mind that employers don't really care about your past," argues Business Insider. "They only ask about it in order to try to predict your future (behavior) with them if they decide to hire you."


How to Answer the Question

There are several approaches to successfully answering this question, but some key things to remember are:

  • Be Honest

Hiring managers can see straight through BS. Make sure that you have a real-life situation in mind and be truthful about the difficulty of the conflict that you faced, but ensure you finish off with how you actually triumphed and overcame the obstacle. Interviewers like to see that a candidate is genuine and humble. From a skills perspective, a manager wants to hear proof that you can face adversity and still achieve your targets.

  • Positivity

Another important quality to show when answering this question is that you remained positive when overcoming a hurdle at work. It’s only natural that the majority of us will feel stressed, but you must show that you can come up with good resolutions. Constructive problem solving is important in keeping a positive company culture, and employers want to make sure each candidate is a fit.

  • S.T.A.R. Approach

An easy way to remember how to answer this question is to use the STAR approach. You must first explain the situation that you were in and how the task was challenging. Then, explain the approach you took and the positive result it had. Remember to keep your answer short and precise; many times candidates find themselves going off on a personal ramble about a situation that doesn’t show any problem-solving qualities.



  • Show How You Work Well Under Pressure

An important quality to show is how you work well under pressure. When faced with an unexpected struggle, it’s important to show how you quickly resolved it within a limited period of time.

  • Make Your Answer Relatable to the Role You Are Interviewing for

At the risk of stating the obvious, pick an example relevant to the position that you are aiming for. If you know the new job will involve a lot of teamwork, discuss a group project that wasn’t going well or a group task at work. If it is an individual position, then talk about a situation where you had to complete a task that was difficult alone.


Sample Answers

The below examples can give you some inspiration on how to successfully answer this behavioral question:

  • In my last job, we were all set to begin a project when everything that could go wrong, did. While some team members panicked and suggested a delay was inevitable, I suggested we all collect ourselves and lay out alternatives for each challenge. We spent the morning taking action on alternatives and were able to start on schedule. It turned into a very successful project.
  • The greatest challenge I faced in my previous job as a travel consultant, was being on call when the terrorist attacks happened in Paris. I had to ensure all our clients that were currently in Paris were safe, and put them in touch with local representatives that could be at hand if needed. I then quickly devised a report to see who would be flying in the next week and put together two-week, tailor made alternatives for other destinations. Being able to do the above under pressure relayed trust into our clients and several even sent hand written letters to our managing director to thank me for my care and support.
  • When working on a large event in my previous position, I had noticed that a colleague had booked the cake to be delivered a day before the actual event. I quickly found an alternative supplier that could prepare the same cake swiftly and rectified the mistake.
  • When I was completing my first assignment for university, something happened to my laptop. It broke down the night before and I lost my whole assignment the day before I had to hand it in. I tried to download software to find where it had disappeared to but to no avail. Rather than offer up excuses, I stayed up throughout the night and re-wrote the entire assignment on a friend's laptop. It was challenging but I was so relieved that I managed to finish within the deadline.


Mistakes to Avoid

Mistakes do happen on a daily basis but in an interview, you definitely want to avoid making any kind of mistake; after all, one slip-up could cost you the entire job. In order for you to be fully prepared, here are some answers that you should definitely avoid:

Saying You Have Never Faced a Challenge: Not having faced adversity can suggest to an employer that you don’t set ambitious goals, avoid challenges and lack self-awareness. At some point in our career, we face difficult situations that need to be resolved in some shape or form, and if you haven't got any examples to draw on, then it shows that you are happy to coast.

Focusing on a Personal Achievement Rather Than a Professional One: Having survived through tough times is certainly something to be proud of. However, these hard times should be a situation at work that relates to your current or former role. Unless it fits the job, leave that example for outside the interview room.

Focusing on the Challenge Instead of the Solution: When answering this tough question it’s important to specify what the solution was, instead of focusing on just the challenge. Employers want to see how you can think on your feet and resolve arising issues.

Talking About a Time You Were Faced With a Challenge and Couldn’t Overcome It: Whatever you do, don’t tell a hiring manager that you couldn’t overcome the obstacle; it’s the interview equivalent of shooting yourself in the foot. Remember, overcoming an obstacle' doesn't have to mean that you turned an entire department around and made the company a million dollars; it can be something relatively small and simple, as long as it shows that you were able to think on your feet and turn a negative into a positive.



Have you ever been asked how you overcame an obstacle in an interview? How did you answer the question? Let us know in the comments section down below…


This article was originally published in May 2015.