Describe Your Greatest Challenge - Interview Question (+Answers)

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Sep 8, 2022 5 min read

You’ve made it to the interview phase of a job and are preparing for behavioral questions. A very common behavioral question you might encounter will ask you about a challenge or conflict that you’ve encountered.

Don’t be caught off guard!

This article will provide some tips on answering this question like a pro!

Looking for other tricky Interview Questions and our take on their answers? Check out these:

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  4. How To Answer: "What's Your Biggest Weakness" In An Interview
  5. What Other Companies Are You Interviewing With? - Interview Questions and Answers
  6. How To Answer 'What Was Your Greatest Accomplishment?' In an Interview
  7. How To Ace 'Tell Me About A Time You Failed' Job Interview Question
  8. How To Reply To "What Sets You Apart From Other Candidates"?
  9. What Are You Passionate About: Best Interview Answers

Why is the “Describe Your Greatest Challenge” question important?

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Work, just like life, never goes according to plan.

Ideally, that client project you are leading goes smoothly, everyone is happy and there are no problems. In reality, however, that is not always the case and recruiters want to know how you think, adapt, respond and learn from anticipated as well as unexpected challenges.

Is the measure of the best candidate who is best when things go well, or who is best when responding to difficult challenges? The short answer is, they evaluate both scenarios in an interview.

What do Hiring Managers look for in your answer?

One of the key things hiring managers look for in this answer is honesty. Talking about challenges or conflicts can be a touchy or tricky subject, and recruiters scrutinize this question even more so.

Another key thing they look for is whether you’ve learned anything from the experience or how you approach a similar situation differently now. Even though this is not explicitly asked all the time, it is extremely important that you include what you learned and what you do differently now.

Finally, think about why they are asking this question to understand what they are looking for. As mentioned earlier, they want to see how you respond when things aren’t going according to plan. In this light, it is more important to communicate what you were thinking and why, while focusing a little less on the details of what actually happened.

Some detail is necessary for context, but don’t go overboard painting the story with granular details and risk losing sight of why they are asking the question.

One thing to consider is the context in which things might not go accordingly. Joining an early stage startup, for example, has a lot of uncertainty and risk as part of the work environment. Recruiters might therefore put more weight on this question and even follow up with more questions as a result.

How do you answer the question “What is your greatest challenge?”

There are many ways to answer this question, but what I recommend for my clients that book interview preparation is to use the STAR method for behavioral questions that require an example to answer.

STAR stands for situation, task, action and results. It is an easy acronym to remember that will hit all the key points you need to touch on to answer the question effectively.


Set up the situation of the example you are using for your answer. Try not to generalize this part of the answer and add some specific details. Make sure you don’t spend too much time on this step, but also don’t overlook it.

Example: When I was a Senior Consultant at Deloitte in 2018, I was tapped to lead a Digital Transformation project for a top 5 Banking Client. One of the problems, though, was that the project would begin during a reorg going on in the company.


What goals were you working towards? What were you asked to do, or what were your deliverables?

Example: The client had some clear goals and priorities, including an aggressive 12-month timeframe on a strict budget of $10M.


Describe the actions you took to address the situation with an appropriate amount of detail and keep the focus on YOU. What specific steps did you take and what was your particular contribution? Be careful that you don’t describe what the team or group did when talking about a project, but what you actually did. Use the word “I,” not “we” when describing actions.

Example: I made sure I had the right team around me for the project and hired, trained and developed 5 people to execute on the plan. We worked with 15 stakeholders to develop a 3 phase timeline that addressed the challenges of the reorganization by getting buy-in from senior management to sign off on key decisions.


Describe the outcome of your actions, and don’t be shy about taking credit for your behavior. If possible, try to quantify results.


We were able to complete the project 1 week ahead of schedule and $500k under budget. The client was extremely satisfied with the result and signed a new contract to extend the project.  

Additional tips to help you prepare for the “Describe your greatest challenge” question

One of the most important things to remember when preparing for this question is picking the right example to use. Pick an example which you can provide details if there are follow-up questions.

Write out your answer beforehand. This allows you to record key details you might have forgotten if you just answered from memory.

Practice your answer. You can practice it with a friend to get it just right. Alternatively, you can record your response and edit it based on the recording.

It is ok to ask for a moment to think or decide. When caught off guard by complicated or “gotcha” questions, saying “that's an interesting question, let me think about it” buys you time to organize your thoughts and respond with a more effective answer.  

Takeaways: Describe your greatest challenge

The STAR method remains a quick and  effective way to answer behavioral questions. Make sure to keep each part of the method the right length of communication.

You can add what you learned and what you currently do to prevent this challenge from occurring again.

Make sure the length of your answer is not too long, but also not too short.

And, you can always book a free intro call with me and discuss your interview challenges together.

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Paul Tran
Career Counseling Manager | Resume Writer | Partnerships @ Enhancv Crafting your message: from Students to Executives
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