Tell Us About a Time When You Found it Difficult to Work With Someone

Tell us about a time when you found it to work with someone

In your job interviews, you’re likely to be asked about a time when you found it difficult to work with someone.

Coming up, I’ll share exactly how to answer this question in your next interview, with sample answers…

I’ll also share a critical mistake you should avoid when answering because it can cost you job offers.

Let’s get started…

Why Employers Ask This Interview Question

Here’s why employers ask you about a time you found it difficult working with someone:

In almost every job, you’ll encounter difficult people, whether it’s customers/clients, or even team members.

The employer wants to know how you’ll handle future situations, and they feel their best shot at this is to understand how you’ve dealt with difficult people in the past.

So, hiring managers are listening for a few key factors in your response:

  • They want to make sure you can handle conflict and difficult personalities.
  • They want to understand how you communicate (and how you listen).
  • And they want to make sure that your overall approach to working with people fits with the current team and workplace culture.

How to Answer Interview Questions About a Time When You Found it Difficult to Work With Someone

The best answers to this question will show how you stay calm and professional and focus on getting a positive outcome for the company, even if a team member or customer is difficult to get along with.

When coming up with a good example for your answer, try to look for a story that is relevant to the job you’re discussing, had a positive resolution, and taught you a valuable lesson, too.

One warning: this question is not an invitation to badmouth.

Hiring managers don’t want to hear job seekers complain about the difficult person; they simply want to hear how you handled the challenge.

So when answering this interview question, explain briefly explain the situation, the person involved, and why this person was so difficult to work with.

But focus more on describing how you overcame the challenge of working with this person.

How did you bring the situation to a positive outcome, and what did you learn from it?

The best answers will end on a positive note. Hiring managers will be concerned if you share a negative story and dwell on the negative aspects of the experience.

When answering this interview question, it’s critical to show a positive attitude along with a positive outcome.

This is why it’s a nice touch to end your answer by sharing a lesson you learned.

The Best Type of Example/Story to Choose

Most people can think of more than one difficult person they’ve had to deal with, so which type of story is best to choose for your response?

Your best option is to share an answer that fits the role you’re discussing. Think of a past example that relates to how you’ll be dealing with people and communicating in your next job.

In a job interview, the employer isn’t just deciding whether you seem smart and competent overall.

They’re far more interested in whether you seem able to step into this exact job and handle the technical aspects, based on your past experiences, hard skills, etc.

If you’re interviewing for a customer service position, try to come up with a great example of a difficult customer and how you did an excellent job of winning them over.

If you’re interviewing for a sales job and you have previous sales experience, give an answer that shows you how turned an extremely difficult prospect into a customer.

If your role is more focused on internal collaboration and communication, give a specific example of how you handled a tough situation with a team member in your last job.

And if you’re an entry-level job seeker, then of course you’ll need to point to someone difficult to work with in your academic work. This could be faculty members, a classmate or team member, etc.

Overall, you’re more likely to make a good impression on the interviewer if your answer shows that you’re prepared for the exact type of work that you’ll be performing in this job.

6 Traits that Hiring Managers Look For in Your Answer

When answering interview questions about a time when you had to work with a difficult person, you’ll help yourself win the job by demonstrating the following traits:

  1. Professionalism
  2. Strong interpersonal skills and listening skills
  3. Patience
  4. An approach that keeps the company’s best interests in mind
  5. Optimism and a positive outlook
  6. An ability to learn from tough experiences and recognize the key takeaways from a difficult situation

If you can give an answer that shows the above traits, you’re going to make a good impression in your job interview.

Coming up, let’s look at word-for-word examples of a good answer…

Sample Answers to “Tell Me About a Time When You Found it Difficult to Work With Someone”

We’ve covered a lot of steps and key pieces that the best answers should include.

So let’s pull all the advice above together.

Here are word-for-word sample answers to describe a time when you found it difficult to work with someone.

Example Answer 1:

In my last job, the company hired a new project manager who started overseeing some of my work. She had a strong, outspoken personality and I wasn’t accustomed to working for someone like this.

She was also critical of my work and pointed out mistakes rather frequently.

Instead of reacting right away, I took a couple of days to think about how to best approach this situation.

I decided that this was simply her leadership style, and I needed to adjust. I realized that she was pointing out areas for improvement in my work because part of her job as a leader was to help me get better.

I realized that she meant well, even though I wasn’t used to her abrupt style.

So I made it my goal to learn to get along with her, build rapport, and incorporate her suggestions and feedback into my work.

I ended up building a great relationship with her and learning so many valuable lessons from her, in terms of how to do my job better and succeed in this industry.

The experience taught me a lot about working with all different personality types and how to take criticism and feedback the right way.

Example Answer 2:

In my last customer service job, I was approached by a customer who was angry about a phone conversation they’d had with a different customer service rep.

This was the first meeting between the customer and myself, but they were shouting from the beginning.

I asked questions and calmly listened to avoid escalating the situation, which worked well.

By using active listening, I was able to determine the issue. They had been promised a full refund for a faulty product but were then told that we would only be issuing them a replacement unit instead.

I was able to apologize for the mix-up, make sure they felt heard and understood, and provide a solution.

In this case, they were entitled to a refund, and I handled it on the spot.

The customer appreciated this and returned two weeks later to buy a different product from us, which was fantastic to see. My manager noticed this and told me they appreciated my efforts in winning this customer’s trust back.

Example Answer 3:

In my current sales representative role, I recently had to lead a meeting and sales presentation with a potential client who was quite difficult to communicate with.

He was combative, felt like he already knew our product wasn’t a good fit, and didn’t seem open to absorbing new information.

Still, because I took the time to prepare a presentation with examples of how a few of his competitors were using our software, and their real-world data and results, he agreed to try us out for a test project and give our company a chance.

So I think in this case, my key to winning over this client was to over-prepare and demonstrate exactly what was in it for this client, and what they were missing by not working with us.

Example Answer 4:

In my last job, I worked with a colleague who was difficult to collaborate with.

This person wasn’t open to feedback or discussing their work at all, and they didn’t seem interested in being a team player.

I wasn’t the only person they took this attitude with, either. Our project manager had struggled to get this person to integrate with the team.

I came up with a solution, though:

I talked to this person and explained that the reason I was asking certain questions about their work was to make sure we were on the same page and to ensure that the project would be a success.

I explained that I wasn’t checking or judging their work, but simply trying to improve the overall project.

Meeting and talking with this person helped them understand where I was coming from and that we have the same end goal: a successful project that made us both look great in the company.

By clarifying and communicating better, I resolved a difficult situation and got them to buy into the team effort.

Their communication and work ethic improved, and I was able to produce better work after this talk, too.

The project ended up turning out great, and although this person gave their two weeks’ notice and left the team later that year, we were able to work better together during their time on the team.

Use the STAR Method to Organize Your Answer

With this interview question or any behavioral questions (questions beginning with phrases like “Describe a time when…”) I recommend organizing your answer with the STAR Method, which is short for:

  • Situation
  • Task
  • Action
  • Result

This ensures that you’re telling a clear, concise story to the interviewer and helps you know where to begin and end your response.

Otherwise, one of the big ways you can go wrong in your interview is to get sidetracked, fail to tell a clear story, and realize you’ve talked for three minutes and still haven’t been able to describe what you wanted.

So as you think back to a difficult person you worked with, begin with the situation. What job was this? When did this occur? Who was the person?

Then, describe the task at hand. In what capacity were you working with this difficult person, and what goal did you need to achieve?

Next, talk about the action or approach you took in dealing with this difficult person.

And lastly, talk about how you got a positive result and describe any lessons learned from this difficult colleague or customer.

Remember to keep the story positive. Unless the hiring manager specifically asks for an example of a time when you failed, you shouldn’t be sharing a negative story.

Conclusion and Key Takeaways

To recap, many companies will ask an interview question about a time you had to deal with a difficult person.

Make sure your answer shows professionalism, communication, patience, and problem-solving skills.

When you think back to the difficult people you’ve encountered, choose an example that is relevant to the job you want and had a positive outcome.

And in general, when answering behavioral questions in your interview, try to tell a clear and concise story without getting sidetracked.

Use the STAR Method that I explained earlier to organize your response, and aim for an answer that’s 30-60 seconds long.

By showing you were able to get a positive result despite a past conflict, you’re showing the hiring manager that you can turn a future negative situation, conflict, or difficult person into a success, too.


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