In 2007, The Bucket List starring Jack Nicholson and Morgan Freeman popularized the idea of writing down your life dreams—things you aspire to do before you “kick the bucket”—and finding a way to make them happen. This lesson introduces a different sort of “bucket list,” one that’s intended to help you gain wisdom rather than to fulfill wishes.

Everyone we meet has the potential to teach us something. Of all the sources of knowledge available to us in the Digital Age, the richest repository of wisdom still resides in the hearts of the people we interact with each day. The Internet can help us track down information, but life’s deepest truths are best learned in the context of relationships, from people who have lived and breathed them.

According to an ancient Hebrew aphorism, “Counsel in the heart of man is like water in a deep well, but a man of understanding draws it out” (Proverbs 20:5, Amplified version). Well-crafted questions are like buckets that leaders can lower into the souls of others to draw on their wisdom. By inquiring into the life experiences and accumulated insights of others, a leader nourishes her mind and enlarges her fund of knowledge. At the same time, these questions are revelatory. They allow a leader to learn about the hopes, dreams, and concerns of their people.

A Leader’s Bucket List of Questions

What is the Greatest Lesson You Have Learned?

This question enables you to draw out principles of wisdom that others have acquired over the course of their lifetime. Typically, people need prep time to be able to answer this question well, so you may want to give advance notice before seeking a response to it.

What Are You Learning Now?

This question uncovers another person’s passion. People aren’t passionate about something they discovered twenty years ago. Although past lessons may have profoundly shaped someone’s convictions and beliefs, they don’t have the same capacity to kindle and excite the emotions as a fresh insight does.

How Has Failure Shaped Your Life?

This question highlights the importance of attitude. Adversity reveals more about people than anything else. Once you know the battles someone has been through, you’re far better suited to assess their character.

Whom Do You Know That I Should Know?

This question is all about networking. The best leaders continually seek to connect with people who have specialized knowledge or expertise. We often must travel beyond the bounds of our immediate circle of friends and family to access the knowledge and opportunities that can take our leadership to a higher level.

What Have You Read That I Should Read?

This question aids personal growth. As leaders, we don’t develop in a vacuum. We have to equip ourselves with resources that can challenge our thinking and expand our horizons, and others can guide us to them. 

What Have You Done That I Should Do?

This question clues us into experiences that have the potential to expand our influence. Leadership is more caught than taught; we learn by observing and doing as much as by reading and researching. Others can expose us to training initiatives, mentoring programs, and other interactive learning environments that can stretch our abilities to lead.

How Can I Add Value to You?

After you have learned from a person, the greatest way to say thanks is to offer to serve or help them. Expressing gratitude in a practical way honors the other person, adds value to them, and builds goodwill for the future.

Thought for Application

Think of two leaders whom you deeply admire and with whom you have enough of a relationship to schedule a one-on-one appointment. Set up a time to talk with them, bring your bucket list to the meeting, and be prepared to capture the insights they share.

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