How to Answer “Tell Me About a Person Who You Found Most Challenging to Work With” (With Sample Answers)

flat art illustration of two coworkers having an argument

Why do employers ask this question?

Employers ask this question to gauge your ability to work with difficult people and handle challenging situations. They want to see how you handle conflict and whether you are able to find a way to work effectively with someone who may be difficult to work with.

How to answer the question

  1. Describe the person you found most challenging to work with and provide context for the situation. Be specific about the challenges you faced and how you dealt with them.
  2. Discuss the actions you took to try to improve the situation. This could include seeking additional support, finding ways to communicate more effectively, or finding common ground with the person.
  3. Emphasize the positive outcome of the situation, if possible. If you were able to find a way to work effectively with the person and complete the project or task successfully, be sure to mention it. If the situation was not resolved, discuss how you were able to continue working effectively despite the challenges.

How to prepare for the question

  • Think about a specific person you found most challenging to work with and how you handled the situation. It could be a coworker, a client, or someone else you had to work with.
  • Practice describing the person and the challenges you faced in a clear and concise manner. Focus on the actions you took to try to improve the situation and the positive outcome, if possible.
  • Emphasize your ability to handle difficult people and situations in a professional manner. Avoid coming across as confrontational or inflexible.

Remember, everyone has to work with people who are challenging at some point in their career. How you handle those challenges is what matters. By showing that you are able to find a way to work effectively with difficult people and handle challenging situations, you demonstrate your ability to be a valuable team player and adapt to different working environments.

Common Mistakes

1. Being confrontational or disrespectful It's important to remain respectful and professional when discussing a person who you found challenging to work with. Avoid being confrontational or disrespectful in your language or tone. Even if you had a difficult time working with this person, it's important to remember that you are being evaluated on your ability to handle challenging situations in a professional manner. 2. Failing to provide specific examples It's important to provide a specific example of a person you found challenging to work with, rather than simply saying that you "sometimes have to work with difficult people." Providing specific examples shows that you have experience handling challenging situations and can provide concrete examples of how you handle it. 3. Not demonstrating resolution or compromise Employers want to see that you are able to effectively handle challenging situations and work towards resolution. If the situation was not resolved, it's important to discuss how you continued to work effectively despite the challenges. If the situation was resolved, discuss how it was resolved and what you learned from the experience.

Sample Answers

  1. "One person I found most challenging to work with was a colleague who had a very different communication style than me. They would often interrupt me or talk over me in meetings, and it was difficult for me to get my ideas across. I found it challenging to work with them because it felt like they weren't listening to me. To improve the situation, I made an effort to communicate more effectively by speaking up and making eye contact when I was speaking, and I also tried to find common ground by finding areas where we agreed. Ultimately, we were able to work effectively together and complete the project successfully."

  2. "There was a time when I found a client most challenging to work with because they had very specific and demanding requirements for a project. It was difficult to meet all of their demands and still keep the project on schedule and within budget. To improve the situation, I worked closely with the client to understand their needs and priorities and found ways to meet their requirements while still being efficient. By working together and finding ways to compromise, we were able to complete the project successfully and maintain a good working relationship."

  3. "One person I found most challenging to work with was a supervisor who had a very hands-off management style. It was difficult for me to get guidance and feedback from them, and I often felt like I was working on my own. To improve the situation, I made an effort to seek out additional support and guidance from other team members and found ways to stay connected with my supervisor, even if it meant reaching out to them outside of regular meetings. Ultimately, we were able to work effectively together and complete the project successfully."
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