10 Questions Great Bosses Ask Themselves

Humble reflection is critical to excellent leadership

7 min readOct 26, 2021


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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 always right.

Good leaders ask themselves these questions especially if an individual or the entire team is underperforming. As Navy SEAL Leader Jocko Willink says:

“There are no bad teams, only bad leaders.”

Bad performance is always a leadership problem. If you don’t look at it that way you’ll never correct things in a productive way.

Because of this, a good leader always looks in the mirror first when something is going wrong while a bad leader points fingers.

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.” — Margaret J. Wheatley

#2. Am I Prioritizing Well?

This one seems obvious but many people, including bosses, have a hard time prioritizing their actions to maximize their effectiveness.