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

employee overcoming obstacle

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 who is resilient when facing 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. The business insider reported: "Throughout the interview, keep in mind that employers don't really care about your past. 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

  • Be Honest

Hiring managers can see straight through a pile of BS. Make sure that you have a real-life situation 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 goals.

  • Positivity

An another important quality to show when answering this question is to show 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 and how the task was challenging. Then explain the approach you took and the positive result it had. This tip will help you 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 sounding like a broken record, pick an example relevant to the position that you are aiming for. If you know the new job will involve heavy 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.

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 2 week, tailor made alternatives for other destinations. Being able to do the above under pressure relayed trust into our clients and they had sent a hand written letter 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 cake within swiftly and rectified the mistake.
  • When I was completing my first assignment for university, something happened to my laptop. It broke down and I lost my whole assignment six hours before I had to hand it in. I tried to download software to find where it had disappeared to but to no avail. I then stayed up throughout the night and re-wrote the entire assignment. 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, it’s crucial to avoid making any kind of mistake. One small slip-up could cost you the entire job. In order for you to be fully prepared we have listed a few deadly mistakes:

Saying You Have Never Faced a Challenge: not having faced adversity will show that you don’t set ambitious goals, avoid or even notice 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.

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 role. Unless it fits the job, leave that example for outside the interview rooms.

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 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 an obstacle. It’s literally like shooting yourself in the foot and saying that you shouldn’t be employed as you can’t think of any solutions.


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.