What Was the Most Challenging Project You Ever Worked on?

What was the most challenging project you ever worked on?

Ever sat in an interview hall, sweating from nervousness, the interviewer is about to be done and you’re hopeful because you’ve answered everything they’ve asked for so far. But then, they drop the dreaded question- What is the most challenging project you have ever worked on? 

Sounds easy? But anyone who has been asked this very question in an interview knows how hard it can be to give the perfect answer. 

So how exactly do we answer this question?

Simple- Tell them about the most challenging project you’ve ever worked on. No, really. Chances are that the only reason you think that your projects are simple is that you’ve already worked on them. But, for a person who knows nothing about your past work, those projects may sound intriguing and difficult enough. 

All you need to do then is to present your project in such a manner that the interviewer has no choice but to consider you as a potential candidate. But, before we move on to that, how exactly should you select the ideal project to talk about at your interviews? And why do interviewers even bother asking this question?

Everything You Need to Know

This particular question is a great way to let the interviewer know that you’re a perfect candidate. They want to know about your strengths. So, use this opportunity to highlight that. Let them know about your adapting skills, planning skills, and decision-making.

When the interviewer asks you about the challenging projects you’ve worked on in the past, there are certain aspects and elements in your answer that they’re seeking out and analyzing. They want to know how much they would benefit from you as their employee. For this, they focus upon a few things like:

  • How do you deal with challenges?
  • What is your approach towards work ethics?
  • What skills do you utilize when facing a difficult or important project?
  • How do you grapple with stress?

Hence, when preparing for an answer, keep in mind that there’s a much larger purpose of asking you about your past projects and when answered earnestly, the interview can swing in your favor. 

What Project Should I Talk About?

Do not go completely unprepared. Prepare for such questions a day or two before the day of your interview. This question does not require a spontaneous response, and so before the day of the interview, give yourself a few minutes to think about the projects you’ve worked upon so far.

In the case of fresh graduates who may think that they don’t have a very long list of fancy projects that they’ve been a part of, here’s some advice- Consider Everything. If needed, feel free to talk about college projects, society events, and even projects that you took up just for your self-fulfillment. They’re all valid and can be used to boost up your chances of being hired when compared to other candidates.

“So far, I think my biggest and most challenging project has been in University. I had to film a documentary which took me about four months. The project required utmost dedication and detailed research along with studio work, editing, and on-field experience which also required time and capital. The documentary was later screened during a national screening competition, so all that hard work did pay off.”

Remember, the project should not be too old! Your interviewers do not wish to hear about how good of a job or an assignment you got a whole decade ago. Stick to a recent timeline, something maybe a year or two old. You want to give off an impression that you’re constantly striving to face challenges head-on and are keen to add to your achievements. 

Think of projects which are closely related to the job that you’re applying for. You do not want to talk about two distinctive fields in an interview. This goes without saying, but your interviewers, who are trying to hire a designer, probably do not care much about your experience as an engineer. So, try coming up with examples that are closely rooted in the job title you’re applying for. 

In the case of a group project clearly state your role. Even though group projects are a team effort, each individual still plays a distinct role. In case you end up discussing a group project that you worked upon in the past, make sure that you very clearly state what role you played in your group and your efforts that helped overcome the challenge.

To make the process easier, we recommend preparing in advance. A day or two before the interview, pick up your pen and paper and make a list of all your relevant and recent projects. In case you’re stuck, try thinking of all the things you’ve worked on and you’re bound to come up with something. Once you’re done making the list, ask yourself the following questions:

  • What was the goal of these projects?
  • What part did I play in each of these projects?
  • What did I learn from them?
  • Which one required me to make the most of my skills?
  • How recent is the project?

Chances are that by the time you’re done answering all these questions, there’s a project which stands out. Something which changed your work ethic, perhaps your outlook towards handling stress, or even how you approach big projects. The point is to choose a project which not only reflects your skills but also how you benefit from them. They wish to know if you’re resilient enough to take up big and stressful projects and make the best of them and even face day-to-day challenges in a charismatic manner. 

The next step is to think over the project you wish to speak about in your interview and prepare an answer. The answer should not seem very boisterous, however. You need to be confident in yourself, humble, and let the interviewer know that even though you’re proud of your difficult projects, it only adds to your skills.

How To Formulate Your Answer

A challenging project is most likely going to have a certain time, economic, or quality constraints to them. Highlight what the challenge was, the hindrance posed to the overall project, and how you overcame it and delivered. In the end, you can also add how that certain project enhanced your skills and ability to deal with future challenges. 

Your answer should focus on demonstrating your decision-making abilities, deadlines, delegations, etc. 

You can consider referring to the STAR interview technique if you’re looking to give a structure to your answers. It is a straightforward and organized way to give a detail-specific answer which can help you stand out from the rest of the candidates. STAR is an abbreviation for Situation, Task, Action, Result. 

Below, is a more detailed discussion on these headings. 

● Situation

‘Situation’ requires you to describe the specific event- The situation you faced. Start your answer by letting the interviewers know about the project. Describe the what, why, where, and when. Setting the scene in detail from the very start will help the interviewers follow your story more clearly and give you a firmer foundation. Try answering these questions:

  • What was the situation or the project like?
  • Who was involved? 
  • Why did the challenge occur?

A lot of times when referring to a group project, candidates tend to refer to themselves as ‘we.’ While group projects are indeed a team effort, make sure to refer to your efforts separately and distinctively. Use ‘I’ when talking about a specific role you played in the group and your contributions.

“Around a year back, I was assigned a month-long project on the feasibility of Microsoft systems, along with two other people. The project required dedicating long hours to understanding and analyzing Microsoft applications. I mainly dealt with their client-based software, that is, Microsoft Office.”

This is just a sample example of how you can start your answers. Further down, we discuss complete sample answers and what makes them complete.

● Task

Use this opportunity to talk about objectives, issues, and obstacles. Try to highlight the challenging aspect in this part of the answer. Along with that you can also try and expand upon the responsibilities you had during the term of the project and how you managed them.

  • You can use the following questions to try and formulate your answer.

Try focusing upon giving logical reasoning behind everything that you talk about. Answer the ‘why’ aspect of the things that you talk about to give more depth to your answer. 

“I was mostly looking at Microsoft Office Suit because of the amount of experience I have with those applications. One big challenge was the updates. Microsoft Corporation at the time was going through major update changes and so to keep up with those while working on a report, it seemed extremely dizzying.” 

Picture the obstacle. Give it reasonings, depth, and why that challenge was a major one for you.

● Action

Use this opportunity to talk about the actions that you took to resolve the conflict and overcome the challenges. In any case, there must have been something your solution would have focused upon, say leadership, collaborative efforts, or new initiatives. Try focusing upon these aspects and the skills that you utilized while finding these solutions and working upon them.

Here are some questions that you can refer to for a better understanding:

  • What steps did you take to resolve the situation?
  • Why did you go for this specific solution?

“The updates, since they were tricky, I came up with the solution that one of us should focus upon keeping up with journals and news updates so we are always notified of all the changes happening around us. I took the initiative of handling this seemingly extra work.”

It is important to highlight your role as an individual. Talk about your ideas and your initiatives and highlight them so that the interviewer knows what role you played and how important it was for the group as a whole. 


Use this section to give a conclusion. Tell them how your role saved the day. Quantify the result in terms of time, capital, or quality aspects which the company or the organization profited off. However, before doing that let the interviewers know how successful the solution was, why was it successful, and if you as an individual learned something through that experience?

The questions you should try answering are as follows:

  • What was the outcome of your solution?
  • Why do you believe the solution was successful?
  • How did this situation influence you as a person?

“The outcome, even though it added extra work, was successful. In the course of a single month, we were able to keep ourselves updated on all new changes which were taking place and simultaneously add it to our reports. The result was that the report is a compilation of all the latest changes which had happened and all studied its feasibility. It was a learning experience for me too. My teammates and I were able to utilize our skills at researching and writing to keep up with the latest trends and updates giving our report an edge.”

End your answer with a learning experience, showcasing that you’re an individual who is open to adapting to changes and growing as a person at every step. This also gives off the impression of humbleness and approachability.

To better understand how to make up an answer for such a question, we discuss a few sample answers below. Try looking at those and hopefully you’ll get an idea of what your interviewers expect you to answer and how to make the most of this question.

Sample Answers

Sample Answer 01

“One of the biggest projects that I’ve worked upon was during my apprenticeship. I was assigned to work on a new layout for X app. While I started the project rather enthusiastically, I soon realized that my app didn’t just have to be easy to use but also minimalistic, in the sense that it had to look good but not overcrowded. The problem here is that the market was already flooded with similar apps and so to become a competing challenger in such a cutthroat market, I had to give something new. It was a long time before I came up with an idea to personalize the app. 

Users after using the app for a certain amount of time would have access to their history of searches and exploration of the app in the form of minimalistic visuals. The idea was approved by my seniors and a subsequent rise in the capital was also approved. Although it took me a long time and a lot of grieving and brainstorming in the end, I believe, it was all worth it.” 

Sample Answer 02

“My biggest assignment was in the university itself. In a group of four, we had to design our magazines. The project was going to be graded. The problem was that due to the raging pandemic, my group mates and I could not hold a physical meeting, and hence, communication caused a lot of hindrances. We had to eventually work on different devices altogether and had to spend a large amount of time on compilations. 

However, in the process, we overly-familiarized ourselves with collaboration techniques which helped me later collaborate with an international client when I was working as a freelancer. While the magazine started at a rocky start and we were afraid that it would be disastrous, it was not so. Our solution was simple: communicate as much as we can. 

I believed that an online platform would be troubling when working on such a huge group project, but fortunately, I was proved wrong. I eventually learned that connections can be easily formed even on an online platform and across distances.”

Frequently Asked Questions

Q1. Should the project that I talk about be recent? 

Yes, go for a more recent project. You want to give off the impression that you are constantly seeking out newer opportunities and striving for accomplishments.

Q2. How recent should the project be?

It can be 2-3 years old or as recent as six months! Go for the most successful and challenging project you’ve ever worked on. However, the project should not be too old. You don’t want to talk about something you worked upon ten years ago. Go for something considerably recent. 

Q3. What should I talk about if I do not have a lot of experience?

In case you don’t have a lot of experience in a field or industry, likely, you won’t get interviewed for a big management position. In the case of a more junior position, feel free to talk about even smaller projects and assignments. In case you’re fresh out of college, you can also talk about your experience in college, society activities, and volunteering events that you’ve taken part in. 

Q4. How should I formulate my answer in a coherent and organized manner?

The STAR Interview Technique is a straightforward way of focusing upon your event and project in great detail and organizing your experience concisely. If you wish to know more about it, scroll upwards. We’ve discussed it in more detail under the subsection titled, ‘How to Formulate your Answer.’ 

Q5. What if my project solution did not have a successful outcome?

In case your solution was not successful, try not to talk about it. Choose some other project or assignment and focus upon the positives. At the end of that day, the interviewers want to know about what makes you a good employee and you want to leave a good impression on them.

What Was the Most Challenging Project You Ever Worked on?

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