How to Answer: What was the most challenging project you have worked on? in a job interview

In a job interview, there are certain job interview questions that are frequently asked to assess your suitability for a job. These type of questions may look like one of the more difficult ones to answer. However, it’s actually a great opportunity to discuss a great challenge that you were able to turn into a big accomplishment.

In this blog, we will discuss interviewer questions about the most challenging projects you have on, why the interviewer is asking this, and how you should answer. Also, read the most common job interview mistakes that you should avoid. Questions about dealing with challenges are asked for all types of jobs and all different levels. It’s therefore important that you prepare your answers in advance so that you’re able to demonstrate how you deal with challenges and describe what you learned from them.

Other ways the interviewer can ask you questions about complexities or challenges:

Why the interviewer is asking about the most challenging project, you have worked on

The interviewer is interested in finding out how skilled you are in managing projects and situations. In other words, how do you react to complexities, challenges, and new or an unexpected task? As stated earlier, there are several ways the interviewer can ask you questions to find this out. In general, these questions are designed to assess your attitude towards challenges and to find out how you deal with them. The interviewer wants answers to questions such as:

  • What is your approach to dealing with challenges?
  • How do your skills help you successfully finish projects?
  • What is your work ethic like?
  • How do you handle stress?

All these questions are asked to find out whether or not you have the ability to handle challenges, and if you’re resilient when facing complexities. The answer you give to questions regarding complex and challenging projects will give them insights into:

  • Your ability to manage projects and complex situations and the skills you possess to do this
  • The approach you use to deal with situations
  • Your decision-making skills and planning abilities
  • How the company could benefit from your skills and abilities

How to answer job interview questions about the most challenging project you have worked on

Just like other behavioral job interview questions, it’s important to prepare scenarios before the actual interview. By doing so, it’s easier to bring up concrete examples during the interview without hesitating. This shows that you came prepared, that you’re self-aware and that you take the interview seriously. You can imagine that it’s difficult to bring up a full example scenario if you did not prepare these before the interview.

When you’re discussing a project, always start by giving the context of a situation and walk the interviewer through the process of working towards a solution. The best way to structure your answer is, according to the STAR interview technique. This is a step by step process of structuring your answer that will help you convey your answer in a concise way.

STAR Interview Technique

STAR is an acronym for a Situation (S), your Task (T) in that situation, the actions (A) you took in that situation and the Results (R) of your actions. This method is perfect for job interview questions that require you to discuss a scenario, such as questions that being with:

  • Tell me about a time when
  • Describe a time when
  • How have you handled

Below we discuss each of the steps in more detail so that you understand the order of events to discuss to convey a clear and concise answer that gets to the point.


The first thing you do when you’re providing your answer to the interviewer is to discuss the situation you were in. Describe a specific situation or event and give enough detail so that the interviewer understands what you were facing.


Then, describe your task in that particular situation. What was the goal that you were working towards?


Next, discuss the actions you took to address the situation. Focus on yourself and what steps you took and what your contribution was.


Finally, talk about the results of your actions. What exactly happened, and how did the situation end? Also, include what you accomplished and what you learned in the process as well.

Choosing the right example situation

When you’re preparing your example situations, try to create a list of situations that relate to the job that you’re applying for. Providing examples that are relevant to the responsibilities of the job are more likely to give the interviewer the impression that you’re suitable for the position. Also, if possible, select projects that you worked on recently. When you’re providing the interviewer with an example situation of 10 years ago, he or she will not be that impressed and might wonder what happened in all those years after. You don’t want to give the interviewer the impression that the last challenging project you worked on happened a decade ago.

Also, give the interviewer an example of a project that was successful, unless you’re specifically asked for an unsuccessful project. Furthermore, explain what your role was clearly because the interviewer is not only interested in what you did, but also based on what you made your decisions.

Mistakes to avoid

Avoid rambling on about a challenging project you have been involved in. Your goal is to answer the question and keep your answers short and concise. The only way to do this is by preparing your answers before the interview. You can avoid these mistakes by writing down a list of situations you have been in and the characteristics of that particular situation. Detail for each situation how you contributed to them being successful. In addition, as discussed earlier, do not use example situations that had an unsuccessful outcome.

Sample answers to job interview questions about the most challenging project you have worked on

Below you will find an example answer that you can use as inspiration to create and structure your answers.

Situation and Task

‘In my previous job at a marketing firm, I have worked on several challenging projects. One time, when I just started at the company, I was asked to work with a small team on a marketing pitch deck for a new client. We got the project because of our reputation and ability to take on the project on short notice. It was a great opportunity for us to show what we were capable of doing in a short amount of time. Then, two weeks before the pitch deck presentation the client requested us to change the entire plan. It turned out that they were unhappy with our first concept and stated that it differed too much from the initial idea that they had in mind.


We organized a brainstorm meeting with the team to figure out what exactly went wrong at which point in the development of the pitch deck. After several hours we concluded that some parts of the project were developed based on assumptions without clearly asking the client for approval before moving on. I asked if I could take the lead on redeveloping the pitch deck. For me, this was a challenge, as well as a great opportunity.

It was a challenge because I had never created a pitch deck working at this company and we had a short amount of time, but it was a great opportunity because I had experience with creating these decks in several of my prior jobs, so it was a great chance to demonstrate my skills. I overcame the challenge by getting the goals clear of what the client exactly wanted, analyzing their feedback, and setting up small milestones to track progress in the two weeks we had left.


We kept in touch with the client throughout the redevelopment process of the pitch deck and finished and submitted it one day before the deadline. Ultimately the client was very happy with our work, and we are still working with them today.

Include what you’ve learned from the situation

For me, the most important learning from this project is that it’s important to get the goals clear before a project starts. Furthermore, my experience taught me that the best way to work on challenging projects is to create milestones to track progress. Now, at the start of a new project, I focus on the most difficult parts and challenges of the project so that I know as soon as possible if there are any issues or attention areas. If this is the case I have more than enough time to work on this before any deadlines. A detailed plan to work on a project is essential to finish it successfully.’ 

Job Interview Topics – Common Job Interview Questions & Answers

Below you can find a list of common job interview topics. Each link will direct you to an article regarding the specific topics that discuss commonly asked interview questions. Furthermore, each article discusses why the interviewer asks these questions and how you answer them!

  1. Accomplishments
  2. Adaptability
  3. Admission
  4. Behavioral
  5. Career Change
  6. Career Goals
  7. Communication
  8. Competency
  9. Conflict Resolution
  10. Creative Thinking
  11. Cultural Fit
  12. Customer Service
  13. Direct
  14. Experience
  15. Government
  16. Graduate
  17. Growth Potential
  18. Honesty & Integrity
  19. Illegal
  20. Inappropriate
  21. Job Satisfaction
  22. Leadership
  23. Management
  24. Entry-Level & No experience
  25. Performance-Based
  26. Personal
  27. Prioritization & Time Management
  28. Problem-solving
  29. Salary
  30. Situational & Scenario-based
  31. Stress Management
  32. Teamwork
  33. Telephone Interview
  34. Tough
  35. Uncomfortable
  36. Work Ethic