Tell me about the most difficult supervisor you have ever worked with and how you went about working with them.

Explain how you went about working with this difficult supervisor. Give a brief reason why the supervisor was difficult and explain how you worked it out.

Do not talk badly about an old boss. You can describe a person as "difficult" without saying "the guy was an idiot."

"My former boss was a couple of generations older than I was, and he was adamant about keeping all office procedures as they had been for the past 30 years. This caused the whole team frustration, as we were trying to utilize antiquated equipment and processes to keep up in a high-tech world. At first, I made suggestions on how to automate processes, but he just wouldn't hear it. He was a very nice guy in general, and so I just figured I'd do it his way. He was the owner, after all! But we took about a year to do tasks that could have been done in five minutes!"