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

Being able to clearly demonstrate your ability of overcoming obstacles will convince potential employers you’ve got what it takes to do the job.

Reviewed by Chris Leitch

Jobseeker overcoming obstacle interview concept

Being invited to a job interview is both exciting and nerve-wracking. Your application worked, you’ve been shortlisted – that’s great news! The next step is to get on with your interview preparation so you’re ready to convince the employer of why they should hire you.

‘Tell me about a time you overcame an obstacle’ is a common interview question, specifically categorised as a behavioural question. Different employers have distinct interview styles but more often than not, you’ll run into a question of this type, so it’s wise to prepare in advance.

Our guide will teach you exactly how to answer this tough interview question in a way that highlights your aptitudes and relevant experience.

Watch an example scenario below:

1. Understand why hiring managers ask this question

Sometimes, it can seem like an employer or hiring manager just wants to put you on the spot during a job interview, but it’s likely not the case. What interviewers are looking for with their questions is to identify certain skills and attitudes that you possess.

A recruiter is always aiming to advance with the most suitable candidates. This means that not only do interviewees need to meet the basic requirements for the role, but they must also fit in with the company culture and demonstrate certain values.

Any questions asking to give an example of when you’ve overcome a challenge are linked to finding out if you have certain competencies. These include problem-solving skills, resourcefulness, decision-making skills and creative thinking skills.

What employers are looking for with this question will depend on the role, the coveted abilities to make someone successful and the style of working in each company. But you can be sure they’ll be trying to identify your level of self-awareness, your resilience to issues in the workplace and how you handle tough situations.

Employers are essentially using your experience to predict how you’ll adapt in the new position. Therefore, it’s crucial that you develop a strong response to this interview question. This way you’ll be able to present a situation where your attitude and your actions led to an effective solution.

2. Choose an obstacle

To develop a powerful response, you’ll first need to decide on a challenge you’ve faced in the past. To do this, think about what situations could relate to the position you’re applying to and which skills you’d like to highlight through your example. From this, you can work backwards to find a suitable challenge that you’ve faced in your career.

It’s important to choose a situation that is relevant to the job and that will clearly demonstrate the skills you can bring to the role. Go back to the job description to keep in mind the pertinent requirements and responsibilities of the position.

The ideal scenario would be to choose a challenge you’ve faced before that is likely to come up in this role. This will give the employer sufficient evidence of your suitability.

Remember to be honest. Describe a real situation but don’t choose an obstacle that would make the basic tasks of the role difficult to complete. For example, if you’re applying for a customer service position, having trouble talking to different people won’t highlight your fitness for that role, even if it’s something you’re learning to deal with.

3. Describe the obstacle

Once you’ve decided on an appropriate professional challenge that you’ve overcome, you’ll need to construct your story. Storytelling is a sure-fire way to engage your listener. You can do this by using the STAR method.

The STAR method (Situation, Task, Action, Result) is a technique for relaying anecdotes in a professional manner that highlights the important information and keeps your answer on track.

In this step, you’ll begin by explaining the first two parts: Situation and Task. This means you’ll give context and describe the circumstances around the challenge. You could explain your role briefly, how you came up against the obstacle and what possible consequences it could have had, if left unattended.

This part is about providing background information and setting the scene. Remember that this step isn’t the main focus of your answer, so it should be concise and brief.

4. Explain the steps you took to overcome it

Moving on to the next part of your answer, you’ll need to describe the Actions you took to overcome the challenge. This means discussing how you were able to deal with whatever issue arose.

You should dedicate some time to reflecting on how you can clearly explain your thinking, planning and execution to overcome the obstacle.

Here, you should detail how you took on the problem and turned it around. You can describe tools used or techniques employed as well as include information that demonstrates your teamwork, communication and leadership skills.

5. Finish with the lessons you learnt

Finally, as part of the STAR approach, you’ll need to end your story by illustrating the Results. You can do this by explaining the favourable outcome of your actions. Were you able to resolve an issue for the future, change a process or reach an objective? Did you receive positive feedback or generate new sales? Talk about each successful aspect of this situation.

If applicable to your story, mention any quantifiable results too – employers like to hear about measurable successes.

One of the worst interview mistakes that some candidates make is forgetting to comment on the lessons they learnt when they were faced with a challenge. It’s hugely important to discuss any skills you acquired or what you gained from overcoming the obstacle.

6. Remember to emphasise key soft skills

Additionally, throughout your story and as part of the conclusion, you should highlight the soft skills that you possess which allowed you to tackle this challenge.

Any examples you give should demonstrate your ability to work under pressure, your positive attitude, your critical thinking or your proactive nature.

By describing these traits, you’ll be ticking boxes for the interviewer. They need to see that you’re able to make decisions that align with the job requirements and the company’s culture.

7. Use example answers for inspiration

It can be difficult to think of specific situations where you’ve overcome a difficulty at work. But it is paramount that you prepare an answer and do not avoid it. By saying you haven’t faced any challenges will portray to the interviewer a lack of objectiveness and self-awareness.

The best job interview tip available is the simple act of preparation. To construct your response, you can read examples of how to answer the question ‘Tell me about a time you overcame an obstacle’ and follow their structures.

Example answers can give you an idea on what kinds of situations people tend to explain and what employers are looking to hear for different positions.

Here are a couple of example answers to get the ball rolling:

Example #1

In my previous job, a colleague fell ill and was unable to continue the project she was working on, which had a tight deadline. As a result, my boss asked me to take it on, being the closest in rank to her position. To be able to deliver the project on time, I delegated some of my usual tasks to colleagues and organised and held meetings with people who had been involved with the project previously. This allowed me to gather as much information as I could to prepare. With some hard work and my new spin, I was able to deliver the project on time, which won us a new client who is still to this day very happy with our service and their personalised project.

Example #2

When working as an office manager, one of my responsibilities was to manage events. I had arranged an executive meeting that was to take place in a few days, when I received a call from our location vendor telling me there had been a double booking and we could no longer use the room we’d reserved. The meeting was scheduled in a different city but through my diligent research, I was able to make some calls and find a new location in time with similar facilities in the same area. I rescheduled the lunch order and requested the necessary equipment for the room. Then I sent out the information to the attendees but also made sure to call them and personally ensure they received the new details and address any concerns. Despite the hitch, I was able to build on my relationships with the executive team as well as proactively started gathering more information to create a database that our team could use in the future if this kind of issue arose again.

Final thoughts

Everyone comes up against challenges in their professional career. It’s understandable, therefore, that employers want to see how candidates overcome them to help decide if that person is a good fit for the role.

There’s no need to fear this question. If you prepare adequately, you’ll be able to truly demonstrate your value as an employee, tailoring your response to the specific responsibilities you’ll be taking on.

In order to avoid the tendency to ramble on, make sure you employ the STAR method and only provide relevant information that will emphasise your skills. Practise your answers, and you’ll be wowing interviewers in no time!

    Have you been asked this question before? Do you have any tips on how to explain workplace challenges in interviews? If so, let us know in the comments section below – we’d love to hear your stories!


    This article is an update of an earlier version published on 19 September 2017.