Tell me about a time you worked with a difficult person.

Added: 5 months ago
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Ajay Thakur
Ajay Thakur 5 months ago

Hi Shikhar, Employers know that difficult people are everywhere and situations come up frequently. Explaining how you’ve been able to handle a challenging person in a mature way demonstrates your ability to manage difficult moments successfully.

In my opinion, these can be the best replies.


"My boss assigned me to a big project that entailed working across multiple teams. I had to collect and analyze data that would help her make an informed decision about a new service we were introducing to our customers.

One of these individuals I needed to collect data from had a bit of a difficult personality. He was late to provide the data, and when he did provide it, it was incomplete or inaccurate.

Without getting the right information from him I knew I wouldn't be able to complete my assignment. After I asked a few times, he agreed to have coffee with me so we could talk about the situation and I could get a better sense of what his challenges were.

I asked what I could do to help make the request easier for him. He shared that he was overwhelmed, as he had multiple competing deadlines, and that there were errors and delays with all the data.

We brainstormed ways that I could break down my request into more bite-size chunks so he could squeeze in the request in between bigger projects.

I then customized each of my requests in a way that would work with his schedule. He appreciated how much I was able to tailor my request to meet his needs. And ultimately, he helped me complete my assignments on time."


"My company had kicked off a highly controversial cross-functional initiative. I was the project lead with a team of three Product Managers, though I was not their direct manager.

One of the Product Managers was many years my senior and a level above me in the organization. Throughout the process, I found that he was working around me, looping me out, and stalling the process by surfacing problems without recommending solutions.

I set aside time for us to chat directly. I shared some of the challenges and pressure I was facing, making myself vulnerable to create space for him to be receptive. I explained the tension I was feeling with regards to our working relationship and asked what I could do to help improve the situation.

This allowed us to clear the air, identify issues, brainstorm solutions, and commit to a healthier form of partnership moving forward.

It was a powerful reminder of the value of communication and the importance of transparency and honesty on teams. Seeing one another in a humanizing light allowed us to build a stronger team."


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