Whenever I interview someone who’s applying for a job I always ask a set of specific attitude questions. Whether the person is interviewing for a senior management position or for an entry level position, one question I always ask is “Could you tell me about your best boss?” You learn an awful lot about a person from their answer to that question. You learn about their attitude toward authority and leadership in general. You learn about how they define “good” and “best”. You learn about how they define “leadership”. You learn about how they prefer to be managed.

These insights can be very helpful in a hiring decision. For example, if someone’s best boss was a person who managed them very closely so they always knew what the next step was, but the position I’m looking to fill requires that a person be able to work independently for a long period of time, the chances are good this candidate is not a fit.

What About the Worst?

I also ask the opposite question, “Could you tell me about your worst boss?” Also very revealing. An interesting thing about the answers I’ve heard to those questions, again whether entry level or leadership level, is that they include statements about how that boss made them feel. “I felt like I was being scrutinized and criticized at every turn.” “She gave me the freedom to ‘fail forward fast.'” From which category, best boss or worst boss, do you think each of those comments came? One of the benefits I have personally received from asking these questions is a kind of measuring stick for my own leadership. When I hear a candidate describe their best boss, it gives me a chance to reflect on whether or not I provide that kind of leadership for my people. Conversely, well, you get the idea.

What About You and Me?

That whole process also makes me wonder whose list I would make. Hopefully, your wondering the same thing or at least thinking about how you would answer those questions. I’ve been blessed to hear from some of my people that they considered me to be the best boss they’ve had. What a humbling joy to hear something like that! Who wouldn’t want to be the best boss someone has had?

How do you become that best boss? Think of the question from the point of view of ”The 7 Habits of Highly Effective People: Habit 2 – Begin with the End in Mind”. Steven Covey suggests imagining you are attending your own funeral. What would you want people to say about you? What about if you were to leave your current position or your company; what would you want people to say about you and your leadership? Whose list of “Best Bosses” would you be on? What does it take to be or become a “Best Boss?” That’s what this blog is all about. Keep checking in and feel free to leave comments.

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