Tough Interview Questions - Who was your worst boss and why?

Following is a tough interview question:

Who was your worst boss and why?

Similar interview questions:
Who was your worst manager and why? Who was the worst person you worked for in your career? Is there a boss you would not want to work with again?

Why the interviewer is asking this question:
The interviewer is seeking to identify potential areas of concern with regard to either your ability to work under authority or your ability to work well with others. It is a minefield question which can lead an interviewer into the opportunity to rant about a bad boss from the past.

The best approach to answering this question:
While there may be aspects about different bosses which are less than ideal, it is important to only focus on a singular quality, rather than the person. No ranting. And if you may have been blessed with great bosses throughout your career, most practiced interviewers will not let you off the hook with a "no worst boss" answer. They will ask which boss was the lesser boss and why. So be prepared to talk about a quality of one of your bosses which could have brought out better results in you or your team.

An example of how to best answer this question:
"I have been fortunate to have a series of good to great bosses throughout my career. If I had to focus on the shortcoming of one of my bosses, it would have been my boss from [company A], who worked well with her direct reports, but was not equally respected by her peers or upper management. As such, she frequently had difficulty getting requests for timely technology upgrades needed for the team. She eventually moved on to another role internally which was more suited for her skills. She was a wonderful person, but she was simply in the wrong role at the time. The manager who followed her was better at enabling our team for success.

An example of how you should not answer this question:
"Wow, where do I begin? Most of my bosses have been bad ones, but I guess the absolute worst boss is the one I have right now. He is constantly riding me to know what I'm doing and when am I going to deliver my project. If he would just leave me alone and let me work, I might be able to actually deliver something. Instead, I spend most of my time in meetings and completing status reports. I've started closing the door to my office so that he would stop bugging me. Now my team members all know my secret knock, and that's the only knock I will answer. If it's not my secret knock, it's probably my boss, so I simply do not answer the door."

Remember to answer each interview question behaviorally, whether it is a behavioral question or not. The easiest way to do this is to use an example from your background and experience. Then use the S-T-A-R approach to make the answer a STAR: talk about a Situation or Task (S-T), the Action you took (A) and the Results achieved (R). This is what makes your interview answer uniquely yours and will make your answer a star!