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What Is The Most Challenging Project You Have Worked On?

The Most Challenging Project You Have Worked On

A commonly asked competency-based interview question is, “What is the most challenging project you have worked on?“. These types 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.


Interviewers want to get more information on how well you can manage projects and challenging situations. Furthermore, they want to assess your approach to dealing with situations at work and how your skills could be of value in the position that you’re applying for.

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.

The best way to answer the questions: “Describe a project you have worked on,” and more specifically, “Describe your most challenging project” is by focusing on providing a concise yet comprehensive response. Begin by briefly outlining the project and highlighting its scope and objectives.

Clearly articulate your specific challenges, emphasizing technical and non-technical aspects. Discuss the strategies and problem-solving skills you applied to overcome these challenges, demonstrating your adaptability and resilience. Conclude by highlighting the positive outcomes or lessons learned from the experience. Keep your response structured and relevant, ensuring that you balance the challenges with the successful aspects of the project.

Other ways the interviewer can ask you questions about challenging work situations and your most challenging project:

In this blog, we discuss why the interviewer is asking you about working on challenging projects. Also, we tell you what you should focus on when answering this question. Furthermore, read more about frequently asked job interview questions here and check our job interview preparation checklist.

Why Interviewers Ask About The Most Challenging Project You Have Worked On

The interviewer is interested in learning how skilled you are in managing projects and situations. In other words, how do you react to complexities, challenges, and new or unexpected tasks?

As discussed earlier, the interviewer can ask you questions in several ways to find this out. These questions are designed to assess your attitude toward challenges and determine 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?
  • Describe your most challenging project

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 answers you give to questions regarding complex and your most challenging project will give them insights into the following:

How To Answer ‘What Is The Most Challenging Project You Have Worked On?’

Like other behavioral job interview questions, preparing scenarios before the interview is crucial. Doing so makes bringing up concrete examples during the interview easier without hesitating. This shows that you came prepared, are self-aware, and take the interview seriously. You can imagine it’s difficult to bring up a complete example scenario if you did not prepare these before the interview.

When discussing your most challenging 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 concisely convey your answer.

STAR Interview Technique

The STAR interview technique helps you to provide a logically structured answer. It’s a way to give the interviewer an answer in the form of a story.

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.

The STAR technique is perfect for answering behavioral interview questions, such as ‘What is the most challenging project you have worked on?’. These questions require you to provide the interviewer with a real-life work example.

Behavioral interview questions often start with the following:

  • Tell me about a time when
  • Describe a time when

Below, the STAR acronym is broken down into steps with more information on what you can include in your answers.

1. Situation

When you give your answer to the interviewer, start by setting the stage. Provide context around the situation or challenge you were facing. Also, make sure to provide relevant details.

When the interviewer asks you questions about challenging situations or projects you have worked on, ensure that you provide all the details necessary for them to understand what you were up against.

2. Task

After you describe the situation, talk about your specific responsibilities and what your role was. The interviewer must get an understanding of your task during that specific situation.

3. Action

Then, talk about your actions to resolve the challenges you were facing while under stress. Provide the interviewer with a step-by-step description of what actions you took.

4. Result

Finally, talk about the outcomes of your actions. Make sure to take credit for your behavior that led to the result.

Here, you answer questions such as What happened? And What results did you get?

Also, provide the interviewer information about what you learned from the situation.

TIP: Make sure to focus on positive results and positive learning experiences.

Choosing the right example situation

When preparing your answers that include example situations about your most challenging project, try to create a list of situations that relate to the job you’re applying for.

Providing examples relevant to the job’s responsibilities is 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 from 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.

Furthermore, give the interviewer an example of a successful project unless you’re specifically asked for an unsuccessful one. In regard to your most challenging project, explain your role clearly because the interviewer is not only interested in what you did but also based upon your decisions.

Learn more about work experiences that you can include in your answers.

Be specific and to the point

Interviewers ask questions about your most challenging project to get more information about how you approach and handle situations. Therefore, ensure you provide the interviewer with what he or she is looking for.

Don’t just focus on a few responsibilities, but be specific and walk the interviewer through what you’ve done to deal with the situation, how you led your team, or how you made decisions. You must explain your thought process in a particular situation you choose to discuss. This is especially important when discussing your most challenging project. The interviewer is interested in relevant details.

Include tangible outcomes

If possible, always talk about the tangible outcomes of your actions. If your actions saved the company money or time, improved a process, or gained a competitive advantage, make sure you quantify this in your answers as much as possible.

Tangible outcomes give your answers more weight and are more convincing to interviewers.

Mistakes to avoid

Avoid rambling on about a challenging project you have been involved in. You aim 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 and 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 Question “Describe your Most Challenging Project You Have Worked On?”

Below, you will find a specified STAR 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 worked on several challenging projects. But the most challenging project was when I had 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 brainstorming meeting with the team to determine what went wrong and 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.’ 

Other Examples Answers to ‘Tell me about a project you worked on?’

Below, you will find more answer examples that you can use for inspirational purposes.

Example Answer 1:

A large-scale website redesign for a client was the most challenging project I’ve ever worked on. This was a complex project involving a lot of coordination with many different stakeholders.

Our goal was to maintain the existing brand identity while maintaining a modern, up-to-date design. The client also had multiple user personas with very different needs and expectations, so we had to ensure we catered to them.

The biggest challenge of this project was the tight deadline. We had to deliver a complete redesign in just two months. This meant that we had to work quickly while still ensuring that every detail was perfect. In order to ensure that all aspects of the project were completed on time, we also had to coordinate our work with other teams and departments.

It was my most challenging project, but one that was incredibly rewarding. We successfully completed the project within the timeline, and the client was extremely pleased with the results.

Example Answer 2:

The most challenging project I have worked on was a web application for a client in the healthcare industry.

The project was complex and had a great deal of technical complexity and large scope. To create an intuitive user experience while maintaining the system’s security, reliability, and scalability, I used a variety of technologies and frameworks, including React.js, Node.js, and MongoDB.

My responsibilities also included developing and integrating third-party services such as Stripe and Twilio into the application and designing and developing custom APIs.

Moreover, I was responsible for ensuring the application met HIPAA compliance requirements. The combination of all of these elements presented a significant challenge, but I was ultimately successful in delivering it within the given timeframe.

Example Answer 3:

The most challenging project I ever worked on was a large-scale website overhaul for a global company. The project involved building a new website from scratch and integrating it with the existing platform.

Due to the large volume of traffic, multiple languages, and integration with numerous third-party applications, the website was a complex endeavor. Furthermore, the website had to be accessible from mobile devices and tablets as well.

From coding issues to design and UX issues, the development team faced many challenges throughout the project. We had to work closely with them to meet the client’s expectations and build the website according to their specifications. Every decision we made had serious repercussions, so we had to consider their implications.

Despite the fact that it was extremely challenging, it took a great deal of effort to complete. For the project to be completed on time and within budget, we had to be focused, organized, and diligent. However, we achieved a successful website that exceeded the client’s expectations despite the challenges.

Key Takeaways

When discussing your most challenging project during an interview, it’s crucial to convey not just the hurdles you faced but also the resilience, creativity, and strategic thinking you applied to overcome them.

Your ability to transform a significant challenge into a notable accomplishment demonstrates your capacity to handle complex situations, which is invaluable in any role. Remember to:

  • Structure your response to highlight the challenge, your actions, and the positive outcome.
  • Use the STAR technique to provide a clear and compelling narrative.
  • Choose examples relevant to the job you’re applying for, emphasizing skills and experiences that align with the role.
  • Focus on positive results and learning experiences, showcasing your growth and adaptability.

In discussing your most challenging project, you’re not just recounting a past experience; you’re illustrating your problem-solving skills, adaptability, and potential value to the prospective employer.

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