10 Questions Great Bosses Ask Themselves

Humble reflection is critical to excellent leadership

Max Klein
7 min readOct 26, 2021
Credit: ESB Professional on Shutterstock

One of the most famous, and best, leaders I served under was General James “Mad Dog” Mattis who eventually became the Secretary of Defense. He said of self-reflection:

“If I was to sum up the single biggest problem of senior leadership in the Information Age, it’s a lack of reflection.”

All leaders must embrace self-reflection to stay focused on why they are doing what they do and evaluate honestly how well they are doing it.

Self-reflection involves asking questions of yourself, answering with humility, then doing something about it. Humility is the operative term because without it you won’t be honest in your answers, especially if the truth involves you needing to improve.

As someone who has studied and more importantly, practiced leadership in military, corporate, and volunteer settings for over two decades, I have seen the below questions asked by the best leaders.

#1. What Can I Be Doing Better or How Am I Wrong?

Arrogant or incompetent bosses think they don’t need to improve. Good leaders know they can always improve and must always improve because situations are always changing and they aren’t…

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