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

 Sample answer 1

By Linda Raynier CPA, CA, Career Strategist

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.

Why this answer worked well:

• She described a tough situation and the difficulties that she experienced with this person.
• She explained the action steps she took and its positive outcome.
• She took the time to understand this individual's issues, which is a crucial skill you need when working with others.

Sample answer 2

By Product Manager Professional

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.

 

Why this answer worked well:

The candidate demonstrated strong leadership with the ability to “manage up” when team members have seniority.

The answer outlined important soft skills like problem solving, communication, and emotional intelligence.

Sample answer 3 By Business Portfolio Manager Professional As a Business Analyst, my job was to create requirements documents or pitches for new projects to present to a board of directors for approval. One of the board members was notorious for poking holes and asked us to gather more information, causing significant delays. This made stakeholders very unhappy. I reached out to this board member to better understand his concerns and identify ways to streamline the process. I looked back at the proposals and identified three themes of concern that kept coming up. We ran proposed changes by the board, and then modified the template accordingly. We also implemented a new practice to share the proposals with the board before meetings to stay ahead of questions. Our approval rates tripled! In the end, uncovering the root of a difficult relationship was beneficial to our process and all parties involved. Why this answer worked well: The answer shows that the candidate has a proactive problem-solving mentality and is capable of turning challenges into opportunities. Resolving this difficulty prevented delays for future projects and improved collaboration with board members and stakeholders.

Sample answer 4 By Marketing & Brand Manager Professional I don’t really believe that there are inherently difficult people. In my experience, different backgrounds and levels of information can make it difficult to understand another’s point of view. As a product manager, I really wanted to push for a shopping feature within our app. I saw a great opportunity to open a new potential revenue stream, but one of our key stakeholders — an engineering team lead — was concerned that we’d need to staff up in a significant way, and that the investment wouldn’t pay off. I did a little digging and spoke to his team members to understand his concerns better. I realized that I would need a quantitative analysis, rather than just a business plan. So I mapped out potential revenue to prove that this endeavor would not only be profitable in the short term, but over the next 5 years. He was impressed that I had run the same analytics as his engineering team would, which helped him move from a blocker to a strong advocate of the project. Why this answer worked well: The candidate showed a willingness to work through a difficult relationship by understanding another point of view. The approach was a blend of soft and technical skills, and the result was a clear win for the company.