Home » Answering “Tell us About a Time When You Found it Difficult to Work With Someone” Interview Question

Answering “Tell us About a Time When You Found it Difficult to Work With Someone” Interview Question

The workplace is not always a very easy place to be in, and you have to manage your tasks as well as deal with your superiors and your colleagues. Instances, where employees have complained about toxic workplaces are rampant enough, and it is not always easy to wade through the murky waters of office politics. Hence, when you start looking for a job again, you prioritize a happy and open work environment where the work culture is inclusive, and you get to be productive and satisfied.

However, although you might have your own personal reasons when you are faced with the question of whether you have found it challenging to work with someone in a job interview, you might find it difficult to answer the question. Even if one person at your previous job made it difficult for you to work in peace or one client you could never satisfy, speaking about them in a job interview might seem quite awkward.

However, there is a way to answer this question.

Why Do Employers Ask Candidates whether they have Ever Found it Difficult to Work with Someone at an Interview?

Why Do Employers Ask Candidates whether they have Ever Found it Difficult to Work with Someone at an Interview?
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Employers often ask prospective candidates the question of whether they have ever found it difficult to work with someone to ensure what kind of person the candidate is. The manner in which you answer the question will reveal a lot about you, and it will tell the employer whether you are only complaining about the person or whether you have taken it in your stride and you have learned anything from the process.

Much will also depend on your employer’s or your hiring manager’s perspective. Hence, it is essential to gauge their perspective before you begin answering the question. You need to understand what your employer means by “difficult.” Does it imply that the person concerned was too much of a perfectionist or that the person was going over and beyond the demands? Unless you have gauged the question correctly, you will not be able to answer the question well yourself.

How to Answer the Question “Have you Ever Found it Difficult to Work with Someone?”

How to Answer the Question “Have you Ever Found it Difficult to Work with Someone?”
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Here are some things to keep in mind while answering this question.

1. Do Not Be Too Negative

While answering this question, you need to ensure that you do not come across as overly negative. Whether the person who you found it challenging to work with was a former employer, a client, a customer, or a colleague, you should not criticize them too much before your prospective employer.

Your employer wants to see how you navigate this question, and coming across too strongly could give the impression that you are not a team player. One cannot expect everything to be smooth sailing at the workplace, and your prospective employer wants to see whether you are a team player or not to take it in your stride.

Unless the person concerned had resulted in physical or emotional trauma at the workplace, you need not be too critical about them. And even then, you should speak about them with utmost professionalism.

2. Learn from the Process

If you have ever found it challenging to work with someone, your prospective employer will want to know what you have learnt from the process. Yes, maybe your previous employer was tough to work with, but did that mean that you became more stringent about your quality of work as well?

Did you become more vigilant about the minor errors you made at work? Or, if it was a demanding customer you were dealing with, did you become more adept at communication and learn how to handle difficult customers better?

Learning something from every difficult situation is always going to pay off in the future, and this is one of those instances where you can truly speak about it to your prospective employer.

3. Be Clear and Concise

When you are faced with the question of whether you have ever found it difficult to work with someone, make sure you answer the question in a clear and concise manner. Keep your response short and professional. You could add a touch of humor, but not at the expense of the person you are talking about.

Simply mention the person who you thought was quite adamant about some of the things at the workplace and how you made sure the issues were resolved to the best of the company’s interests. You could end up by saying what you learned from the process.

4. Do Not Provide Lengthy Anecdotes

Unless you are asked to talk about any particular incident, you shouldn’t start giving lengthy anecdotes. Workplace anecdotes can be very circumstantial- you never know whether the employer or hiring manager sitting in front of you might have done some of the same things that you bring up!

Hence, it is best that you keep the specifics aside and simply answer the question politely and with utmost professionalism. If the interviewer finds merit in your answer, they will ask for more information.

Can You Say You Have Never Found it Difficult to Work with Someone?

Can You Say You Have Never Found it Difficult to Work with Someone?
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One way of answering this question is to reply by saying that you have never found it difficult to work with anyone. It could be true, and this shows that you are very adaptable and can work with any people in any scenario. If that is the case, you could answer that you were fortunate enough not to work with anyone particularly difficult at your workplace.

However, this answer also comes across as too diplomatic, and your employer will know if you are simply saying this to evade the question. Every workplace has some quirks, and it is highly unlikely that you have never had any trouble working with anyone. Answering the question truthfully and professionally will earn you far more brownie points.

How to Answer the Question Based on Specific People?

How to Answer the Question based on Specific People?
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As mentioned earlier, there could be any number of people at work with whom you might have found it difficult to work. Here are some things to remember while answering the question about different people which can help you showcase your emotional intelligence.

1. Boss

Your previous employer might have been a very difficult person to work with, but you cannot say that directly to your prospective employer. Instead, you could say that your boss often put challenging situations in front of you and relied on you to overcome them. You had to brainstorm to develop new strategies, and it has helped you become more resourceful in the long run.

2. Client

Everyone knows how difficult it is to please a client, but you have to get the work right, no matter what. You could say how a client wanted innovative and out-of-the-box ideas, and you had to push yourself more and more to satisfy him or her. On the other hand, if the client had made unreasonable demands, you could go on to say that how you stayed true to company work ethics and did not give in to those unjustified requests but found a way to mitigate the situation. This will show your loyalty to your company.

3. Customer

Dealing with demanding customers is not easy, and you have to satisfy them as they bring the maximum business to the company. You could say how you had to put all your thinking caps on to provide the best possible solution to your customer and how it helped you improve your communication skills.

4. Colleague

You have to work with your colleagues by your side every day, and workplace tensions can hinder productivity. Hence, working with a colleague who always tries to pull you down or tries to take credit for your work can be disconcerting. You could say how you made sure that you became more assertive and that your role in the company was duly recognized.

5. Rival Agents

Sometimes, for their benefit, people from rival companies can try to make things very difficult for you. They often resort to unethical means to gain leads or bring in more clients. Dealing with such agents can be difficult, but you have to make sure that you remain ethical in your approach to work. You could say how you found a better way to one-up the rival and strengthened your communication with your clients and customers so that the rival could not get the better of you.


While answering whether you have ever found it challenging to work with anyone, always remember that the employer wants to know about you rather than the other person who has caused you all that difficulty. Hence, the focus of the response should also be on yourself. Tell them what you learnt from the situation and how you made the most of it. Finally, tell them how you found a way to deal with the difficult person that led to better workplace dynamics. This is undoubtedly going to impress your new employers.