The Four Questions Great Leaders Ask

“Judge a man by his questions rather than his answers.”

—Voltaire

Ever notice how great leaders ask the best questions?

A masterful leader will sit Yoda-like in a meeting, listening intently to the dialogue and then, with Zen Master timing, ask a question that will change the tenor, the focus and the performance of the entire team.

Seeing a seasoned leader ask questions is like watching a great musician or athlete who just seems to know what note to play or what play to call. In my opinion, this rare ability is the performance art of business.

I aspire to be this kind of leader and hope that with age and experience, I will eventually have the wisdom and timing to use less oxygen and get greater results.

(As my mother used to explain—often, I am afraid—God isn’t finished with me yet.)

From my experience, many of the best questions revolve around the following themes. My hope is that by asking these questions of yourself and your team, you get the outcome you want and your people get the leadership they need.

Question 1: Is this urgent or essential?

Urgent matters have a way of getting in the way of the essential. For example, you and your team checking emails first thing in the morning may feel essential but in reality, it may not even be that important. There is a growing school of thought—one that I endorse—that if you start each day by knocking off one or two of the most essential things on your list (before the urgent matters get in the way), you’ll be successful. As a leader, setting the context around what’s super important versus what feels important at the time is a great thing to question.

Question 2: What should you stop doing?

In order to have time to focus on the essential, you must eliminate the less important and distracting activities that occupy your time. Does your team have a “stop doing” list? Helping people become aware of what they might stop doing first will allow them more time and energy to focus on the essential “to-do” list.

Question 3: What makes you feel strongest?

Here’s a well-kept secret: Great leaders know what they suck at. More important, they know how to find working partners with superhero powers that disguise this suckiness through masterful delegation, thus giving them time and energy to focus on their strengths. Just because you can manage a project, drive the P&L, come up with the new marketing hook, and recruit good people doesn’t mean you are passionate and, for that reason, have the potential to be great at all of the above. If your friends or teammates think they are good at everything, lack of awareness and/or humility will conspire to keep them from being outstanding. Asking questions that help focus them on their passions and strengths is a gift that keeps giving.

Question 4: What might we be missing?

Great leaders are open to the fact (and it is a fact) that they are missing something—be it in new service offerings, make up of the senior leadership team, or “simply” in the assumptions they are making about the competitive environment. Pressing the team to consider what WE might be missing, demonstrates humility, awareness and openness to possibility. Wherever you find an innovative culture, you find leaders asking this question.

Extra Credit

The way you ask questions is critically important. By starting questions with “How to” or “I wish” and finishing them with the challenge that you can’t figure out, e.g., “I wish I knew how to get this idea through our legal hurdles,” you are modeling great leadership. Why? Because great leaders humbly share their biggest challenges with their teams and ask them to help solve them.

I was interviewing a young person the other day. As our time together came to a close she said, “You interview inexperienced but driven people like me all the time. Would you mind sharing some of the questions that I should be asking you that I am missing?”

Yoda would be pleased.