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  • Writer's pictureDr. Patrick E. Crawford

What Would You Ask?

Leadership Thoughts | Issue #84

Would you pay $100 for 30 minutes of top leaders’ time to ask seven questions?

Leadership guru John Maxwell did; early in his career, he persuaded top religious leaders to meet with him so he could ask questions about success. A $100 was almost a week’s salary at the time. During this learning session, he asked the following question:

  1. What is the greatest lesson you have learned?

  2. What are you learning now?

  3. How has failure shaped your life?

  4. Whom do you know whom I should know?

  5. What have you read that I should read?

  6. What have you done that I should do?

  7. How can I add value to you?

In 2014 Maxwell published Good Leaders Ask Great Questions: Your Foundation for Successful Leadership. The book’s premise is that to learn, grow and improve requires the ability to ask yourself and your team key questions. John Maxwell is masterful at asking great questions that help to connect people to a vision, improve his team, develop better ideas, and challenge himself.

Four Questions to Ask Yourself

I was first introduced to the Eisenhower Matrix, sometimes called the Urgent-Improvement Matrix, while reading works by Stephen Covey. The matrix can help determine priorities by sorting out the task based on their importance and urgency.

I believe a leader does four things: learn, visualize, strategize, and do. The first three are internal actions, and the fourth is external actions. Many leaders get caught up in the doing that they can’t find time for learning, visualizing, and strategizing. The Eisenhower Matrix provides a framework to think about doing. Everything a leader must consider can be placed into one of the quadrants. The four questions a leader should consider before jumping into the doing are:

  1. Is it urgent and important?

  2. Can it wait and be put into my schedule?

  3. Can I delegate it, and to whom?

  4. What will happen if I don’t do it?

Three Questions to Ask Your Team

Leaders can’t be successful in isolation. Teams are the lifeblood of organizational success. Leading teams is a learned skill that requires intentionality. I’ll save my thinking about the art of coaching teams for another issue of Leadership Thoughts.

The same thing happens with teams, like someone who gets too busy driving the car to see where they are going. If teams don’t take the time to select a destination and develop a strategy for getting there, they are just taking a drive. I recommend the following three questions for teaming.

  1. Where are we going and why?

  2. What are the tactical and strategic strategies to arrive at our destination?

  3. How will we know if we are making progress?

Two Questions for Everyone to Ask

There are four parts to asking good questions. The first step is to determine why to ask the question. Part two is to design one simple one-sentence questions that encourage thoughtful responses. Part three is deciding whom to ask, and part four is when to ask the questions.

Everyone who participates in leadership by asking good questions should consider the following:

  1. Am I asking the right questions?

  2. Am I asking the right people?

Think About!

My good friend and thought leader, Duff Rearick, calls the following a “think about.” I encourage you to consider who (living today) you would be willing to pay a week’s salary for 30 minutes of their time to ask them questions. What are the seven questions you would ask? If you want to turn your think about into a thoughtful learning opportunity, list three people and not more than seven questions. Send your list and questions to me, and I will send you my list and questions.


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