What has been the most Challenging Situation that you have faced? – Interview Question with Answers

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Whether or not you mention about the different types of ‘duties’ and ‘responsibilities’ those you have handled in the past (either on your previous job or in college days), the interviewer is expected to ask this question from you- ‘what has been the most challenging situation that you have faced while being on a particular position or while being in a particular authority?’. This question sure is a ‘challenging’ question in itself because you are supposed to answer it in an appropriate or let’s say modest manner. Since different people have their way of handling different challenges, this question becomes more difficult to answer as you have to come up with a scenario that you have faced and which shows you as a person with the capability to work under pressure and stress and not as a person who holds vanity in making it through that tough situation.

That just makes one part of the question. There is one more, somehow, the latent question that is attached to it. Even if the interviewer doesn’t specifically mention it at first, the candidate is expected to continue the answer to the ‘hidden’ question with the answer to the above question. This question may be one of the hard questions to answer but this one gives you a chance to prove that your candidature is strong enough for the job you are looking for.

What Interviewer is trying to judge?

Is the interviewer trying to judge you or your intelligence on the basis of the kind of ‘challenging’ task that you’ve handled in the past or is there some other motive to it? Yes, of course, there’s some other motive to it. The interviewer is trying to assess your ‘true-potential’ through this question. While seeking an answer to this question from you, the interviewer wants to know:

  1. Your ability to handle stress: Interviewer is interested in knowing to what extent you have faced pressure or stress in the professional capacity, as a job in their company comes with its own-packet of ‘stress and pressure’. So, he/she wants to know whether you can handle it or not.
  2. Your problem-solving skills: It’s not just that interviewer will listen up to your challenge story, but he’ll like to know about your approach to that problem or challenge as well to know your skills of problem-solving.
  3. Evaluating the ‘kind of person’ you are: Since the interviewer will be testing your problem-solving skills as well as your stress-handling ability, this helps him/her to know actually what kind of person you are and how will you act, behave in various situations at work.
  4. Making predictions about the future: The interviewer wants to learn more and more about your past in order to assess your future. The interviewer wants to assess the future ‘you’. So, your potential capabilities for the job can be matched.

While seeking an answer to this question, most of the times, the interviewer is interested in knowing your personality, your challenge-handling capability, and problem-solving ability; however, it may be possible that interviewer asks you this question to know ‘what is the situation that is/was challenging for you’; ‘how do you take the meaning of the word ‘challenge’ and ‘how you see yourself as a person after facing and tackling with that challenge”.


As stated earlier, this question may be one of the most challenging questions of the interview but if you know how to answer this question, you would be able to prove that your candidature is a perfect fit for the job that you are seeking. Forgiving a well-prepared answer, you need to prepare for the following three things:

1. Which was the most challenging situation for you: It depends on person to person. So, define the level of ‘most-challenging’ as per what you feel. E.g.- working on a particular project can be a challenging task for a fresher while that may prove to be an easy task for an experienced professional. Select the challenge of professional capacity.

Think about all the responsibilities and duties those you’ve handled while being on your previous job or the responsibilities those you’ve resumed while being a student in your college times. This might help you to zero-on a situation that fits apt to ‘most-challenging’ definition.

2. How did you respond to it: This tells your ability to work under pressure. This will help the interviewer understand whether or not you will be able to handle all the responsibilities relating to the job in the desired manner. While answering the question, try to inculcate your action/reaction towards the challenge at that particular time when you faced it.

3. How you tackled the challenge: This forms the most important aspect of your answer. After defining what the challenge was all about and your response at first-stage to it; you need to mention your strategy towards solving it. Did you tried to ignore it or you tried solving it? If yes, then how?

Talking about the above mentioned three things in your answer will give weightage to it and help you structure your answer in a well professional manner that will surely impress upon the interviewer.

Tips on what to include and what to avoid


Structuring the answer as per the above points is one thing and knowing particularly about what to include is another. So, giving certain tips about what ‘you should mention’ in the answer to this question:

1. Clarify: You need to clarify the challenge that you faced and in what capacity you faced it? Did you face it being a person in authority or you were working under someone? Also, give clarity regarding the root cause and main problem arising out of the challenge that you faced.

2. Providing resolutions: After defining the problem, you may go on mentioning all the solutions that were available at your disposal. Then talk about which solution you chose and why did you choose that particular solution to tackle that challenge.

3. Stay positive: Staying positive and answering the question with your confidence will make this question easy to crack. Go with a good tone to make the interviewer believe in every positive thing you talk about. More than the problems try to talk about your positive attitude for solving it.

4. Form story: The interviewer will be more interested in knowing a particular pattern of the issues than randomly listening to the challenge and the solution to it. Try to give a proper structure or story-like structure to your answer.

5. Be honest: To impress upon the interviewer, don’t go on making tall claims regarding the kind of challenge you have faced and then your response to it. Go as per the reality otherwise, if the interviewer will be sensing the doubt in your story, this bragging will do a lot of loss to you.

Things to AVOID:

While there are certain things to surely mention or take care of while answering this question, also there are things that should be avoided completely. Those are:

  1. Don’t focus on negative aspects: The question may be negative in some way but make sure that your answer remains positive. Mentioning of the challenge does not mean that you will be just stressing over the challenge and its difficulty level only. Focus on the positive aspect too about your way of handling it.
  2. Mention your response: Many candidates forget or do not specially mention about their response or reactions towards the challenge because they think that they will be judged over it. But, to quite opposite to it they must mention it because otherwise, they are giving an open end to the interviewer to judge anyway about their personality.
  3. Don’t rush: Just in case you encounter this question in the interview without actually preparing for it; then first, don’t ignore or skip this question; second, don’t rush as to talk about it just for the sake of answering it. Answer this question to prove your candidature and capabilities for the job.
  4. Don’t talk ill of the others: While there can be tough situations where you’ll like the company or some other person was the reason that you faced a particular]r challenge. Your interview is not the place to talk about that. Don’t talk negatively; neither about your previous company nor about the employees there.

Preparing your answer:

Now, since you know the purpose of this question, things to include, and to avoid while answering, it’s time to start structuring your answer.

The best strategy to use for this question is to opt for the STAR format.

STAR stands for:
SITUATION: Start by clearly defining the context of the challenging situation. Provide important information to ensure that the interviewer gets an idea about the situation you were facing. You may use the words like- “I was working on a tedious project and suddenly the company gave me the task of developing the website as well.”

TASK: Task aims here to show what you had to do to define the situation as a challenge. What were you supposed to do that was difficult for you. Like in the above example the person was required to develop the website as well as manage his project.

ACTION /APPROACH: Action and your approach define what you exactly and did to tackle the situation. You can start by mentioning what all ways you had. What solutions were available to you and which action you chose and why?

RESULT: The outcome needs to be mentioned. This defines whether you were able to tackle the challenge or not. Mention positively about the result of your action or the approach taken to meet up the challenge.

Sample Answers:


I take every new task or responsibility of my job as a challenge and then try to give my best to come up with the most-right solution to each situation. Talking about the most challenging of all, it was when I was a sales executive during my previous job. I sold a product to a client, which I usually did. Selling was not tough here, handling the consequences were. The product that I sold to the customer reacted to the customer’s skin oppositely. She developed rashes on her skin and was angry enough to sue the company. It would have the worst consequences on the image of my company. I could not have let that happen. The most-tough task for me was to convince her not to sue the company and have a refund and compensation from it. After so long and so much of deliberations I was finally able to convince her to settle for a refund and compensation.


The most challenging situation for me, I would say was when our company was dealing with a big project. All the employees were very serious about this BIG PROJECT because it was one of the largest projects in monetary terms that the company had ever received. The project was, however, in our reach and we would have done it without much of hustling. But, the problem arose here when our software expert resigned in the middle of the project and our work halted. Since I had tried my hands on software’s work earlier, I was asked to do it for that Big Project. It was quite a time since I had done that work. I was afraid that I won’t be able to do it. But, I recalled all that I have learned and gave it a shot and hit the bull’s eye.


The most-challenging situation in my career yet was when my team and I had to manage an advertising job with a very limited budget. The advertisement was supposed to be ‘one of its kind’ as it was for our company’s new range of products. Providing top-notch results with that small fund available was challenging. I discussed it with my team and we finally decided to do much of the work in –house. I encouraged everyone for not losing any hope for the project and that we all will do it together. With the little creativity contribution and complete dedication from every member towards the completion of the task, we were able to produce the desired goal within the required time frame.


During my job in the previous company as an accounts manager, one day, I had to deal with renegotiating the prices with not one but multiple vendors. It was the time when we were facing financial difficulties in the business. I was to renegotiate the payment schedules and requested many vendors to extend the deadlines by 1 or 2 months. It was tough because some of the vendors were fairly new. I thought of a way out. I directly contacted them and asked for a meeting. All the new and old vendors were called so that new ones can have some base for their trust in us. I started by explaining the situation, presented my company’s plan to repay them without causing any loss to them. Finally, we managed to renegotiate three out of the five deals and sailed the company through tough times.


I had to deal with many tough situations daily and many of them have taught me a few ‘life lessons’. The most-challenging situation in my life taught me that ‘quality supersedes quantity’. I used to receive complaints about our business newsletter constantly since I was given the duty to look over the task of the business-newsletter. The complaints mainly were that it never got sent within the deadline and it had a lot of mistakes. It was surely a bad look for the company. I thought upon it and decided to look into the issue. I came up with an idea of cutting down the content to make it easier for delivering error-free content on time. I discussed the idea with the editor and he liked them. Later, the number of complaints about the newsletter is pretty much-low, and in fact, it went on being a super-popular business newsletter.


It is not always that you face a challenging task just out of all professional reasons. Sometimes, your personal life too causes some trouble in your work. I had my work piled up due to my health issues and bad management of time. I had a lot of pressure and stress in completing the work. But I decided that worrying won’t help it and I need to prioritize the works. So, I wrote down all the work I was supposed to complete and segregated them based on submission deadlines. This helped to finish my tasks well in time although I was required to push my limits due to my health I submitted my work on time. This taught me how taking a ‘prioritizing task’ for granted can cost you so much.


It was during my internship-period with a public relations firm. One of the clients suddenly asked to change an entire campaign plan-strategy just one day before its launch. As the client was not satisfied with the first draft that we presented to him; we were required to redo the entire plan. We had to work till late at night that evening to finish the task on time. Thanks to my team which was super-supportive that night and worked for extra hours. This was very challenging because I had to encourage and motivate the team to work for extra time with the same level of efficiency and effectiveness. The next day we gave our presentation and the client was thrilled with the plan. We were able to meet this challenging situation collectively.


The most challenging situation that I have ever faced in my life was when I was given the duty of bringing sponsors for one of the events of my committee. I was head of a student’s placement cell of my college and we had to organize a workshop on ‘Personal Interview and Group Discussion strategy’. The speaker that we talked to had some prior-requirements for those we were supposed to arrange for. The funds that college allotted to us were not enough to incorporate all that was needed. So, I was required to get sponsorship either in cash or kind. It was very challenging for me to convince them as I neither had any prior-experience nor anyone to guide me over this work. But at the end of the day, I was able to convince 3 sponsors for the event, and that even was completed successfully with a lot of positive feedback from everyone.


Every new day at a job brings its own set of challenges and problems those one needs to tackle most effectively and seriously possible. Mentioning the most-challenging situation, I was required to handle a team of such members who were naïve and didn’t know much about the work. I am a serious person and very dedicated to the work. I cannot bear any irresponsibility at the work-space. However the team was quite the opposite, it was carefree to an extent. And it was very tough for me to handle them. But, since I was given the task to train them, so, I thought of handling them their way. In a fun mood and tone, I made them realize how important it is to work seriously. It’s for the benefit of not just the company but for themselves too. That trick worked and the other team-heads praised me for the approach.


Taking up challenges and tackling them effectively is what was taught to me during my graduate studies. It is always a hectic schedule in college for someone who always wishes to try her hands on something new. From assignments to projects to workshops, your time is always filled with some activity or the other. Although all the days are a kind of challenge in themselves, the most challenging time for me was when I tried out something new amid various other things those I was handling. I had my assignments and projects to finish but still, I took on the offer of acting in a stage-play. I had long practice sessions for it because I was to learn a lot and the time was less. Managing that whole was very tough for me. But, I did it with a good time management strategy and ended up with giving good results in drama-acting and all assignments, projects.

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