Better Questions, Better Leadership

I love books that crack through the clouds and send a shaft of light — fresh insight arriving where you least expected it. In my recent reading, The Art of Asking Better Questions delivered exactly that.

Leadership consultant J.R. Briggs makes a compelling case that the questions we ask shape the quality of our lives—our relationships, our leadership, our faith. That promise alone earns your attention.

The return on investing in better questions is remarkably high. Questions build connection. They unlock new perspectives. They create space for growth in others—and in ourselves.

Jesus, the Master Questioner

In His short earthly ministry, Jesus was a prolific asker of questions. His questions called for deep personal reflection, and they consistently opened the door to conversations that led to transformation. Numerically, his questions far exceeded his statements. According to Briggs’ research, Jesus was almost forty times more likely to ask a question than to give a direct answer.

What Your Questions Reveal About You

Here’s something worth sitting with: when you ask a genuine question, you reveal something meaningful about your own character.

You show selflessness—shifting focus from yourself to someone else’s interior world. You demonstrate humility—your questions signal that you don’t presume to have all the answers. And you display courage—because some questions are genuinely hard to ask.

A Starter Kit for Deeper Conversations
The next time you sit down with someone, come prepared with questions that are designed to go somewhere deeper. Here are a few that I carry with me, but be sure to create some of your own:

• What’s an area you’re working on to enlarge your leadership influence?

• Are you leading during this season out of overflow or exhaustion?

• What refuels your soul?

• What is God asking you to trust Him with right now and how do you feel about it?

• What are you saying yes to that may require a no somewhere else?

• In what ways are the people closest to you flourishing under your leadership?

• How do you encourage others to stay strong in their walk with Jesus?

• What relationships are helping you stay honest before God?

• If Jesus evaluated your leadership today—what would He affirm, and what would He need to call to your attention?

In a world filled with talkers, let’s change it up. Let’s lean in and listen by asking thoughtful questions—questions that create heart-to-heart connection and lead to long-term benefits.

Chuck Olson
Founder | Lead With Your Life