How to Answer “Tell Me about an Obstacle You Overcame”

Jumping those hurdles will make you look good.

Reviewed by Chris Leitch

Jobseeker overcoming obstacle interview concept

Being invited to a job interview is both exciting and nerve-wracking. Your application worked, and 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 categorized as a behavioral 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.

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 that 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.

Tips for crafting a response

So, how do you go about answering “Tell me about an obstacle you overcame”? The following tips will help you prepare an effective response:

1. 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 for, 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.

2. 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 and 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.

3. 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.

4. 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 favorable 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 learned 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.

5. Remember to emphasize 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.

Example answers

It can be difficult to think of specific situations where you’ve overcome a difficulty at work. But it’s 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 five 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 organized 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 personalized 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.

Example #3

In my previous role as a marketing coordinator, we faced a significant challenge when launching a new product. Just two weeks before the scheduled launch, our primary social media platform, which was crucial for our marketing campaign, unexpectedly changed its algorithm. This change drastically reduced our content's organic reach and engagement.

Recognizing the potential impact on our launch, I quickly assembled a team to brainstorm alternative strategies. We decided to pivot our focus towards a multichannel approach to diversify our reach. This included increasing our efforts on other social media platforms, enhancing our email marketing campaign and partnering with influencers relevant to our target audience.

Despite the initial setback, our adaptability and swift action paid off. The launch was a success, surpassing our initial engagement and sales targets.

Example #4

When I was working as a project manager, I encountered a significant obstacle when a key team member unexpectedly resigned during the critical phase of a project. This departure left a crucial gap in our team, threatening the project's timeline. To address this, I immediately devised a plan of action.

First, I met with the remaining team members to reassure them and redistribute responsibilities to maintain momentum. I also conducted a rapid recruitment process to fill the vacant position, leveraging my network and reaching out to industry contacts for referrals.

We successfully onboarded a new team member who quickly integrated into the project and made valuable contributions. We not only overcame the obstacle but also delivered the project ahead of schedule.

Watch an example scenario below:

Mistakes to avoid

When tackling this question, it’s important to keep the following things in mind to avoid giving the wrong impression to hiring managers.

1. Exaggerating

It might be tempting to embellish your example to emphasize how you overcame an obstacle at work but you’d only risk making your answer look hyperbolic and exaggerated. This, in turn, risks your credibility and could even take you out of the running for the job. Make sure to be truthful with your response, offering an accurate account of events.

2. Blaming others

Obstacles often arise because of someone’s error or actions, but this shouldn’t be the central point of your answer. Whether it was you or a former colleague who may have caused the situation you’re describing, don’t fixate on that detail. The goal is to showcase how you overcame the obstacle, not who caused it in the first place.

3. Going into too much detail

When using real examples from your previous job, you must be cautious about providing too much information about a situation. This is because you could accidentally share sensitive or private details about your former employer, causing alarm bells to prospective ones. Interviewers must know that you’re a trustworthy and discreet individual who won’t divulge their organization’s information.

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 emphasize your skills. Practice 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 a partial update of an earlier version originally published on September 19, 2017, and contains contributions by Melina Theodorou.