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

Following is a tough interview question:

Who was your best boss and why?

Similar interview questions:
Who was your best manager and why? Who was the best person you worked for in your career? Have you had any "star" bosses in your career? What makes a great boss?

Why the interviewer is asking this question:
The interviewer is seeking to understand your perception of best working environment and what type of manager motivates you. The question will also give insight into how to best manage you as a potential future employee, so it is often asked by your potential future manager.

The best approach to answering this question:
Ideally, you will have more than one great boss over the scope of a career. However, you can answer the question succinctly by focusing in on one manager. The key is to focus on two aspects: 1) the managerial aspects of the boss; 2) how that boss brought out the best in you. While you may have had a boss with whom you connected as a personal friend, the personal nature of the relationship is not an area where you should focus. Stick with work behaviors on both sides of the relationship. And tie it to measurable deliverables resulting from that relationship.

An example of how to best answer this question:
"I've had several great bosses in my career. Probably the most notable would be my current boss. She is a true strategic thinker and able to articulate the company vision and mission in a way which focuses the energies of those reporting to her to achieve high quality results. It was under her personal direction and encouragement that we pursued an entirely new product line focus, which expanded our market share within the broader category from 4% to over 6% in just 3 years. She was the visionary and she worked closely with me to implement this vision at the tactical level within our team. Would you like to hear more about the implementation project?"

An example of how you should not answer this question:
"Most of my bosses have been way too involved in what I am doing, while I prefer to work alone. Probably my best boss was when I was a summer intern in college where I was given one project to complete and then he pretty much left me alone. At the end of the summer, I presented my results, which I did pretty much on my own. It wasn't exactly what they were looking for, but it gave me the opportunity to interpret things in a creative way. So I guess the best boss is someone who gives me time to myself."

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!