7 Practical Ways You Can Grow to Ask Better Questions

Cultivating diverse and vibrant conversations

Part 3: This is the third of a three-part series on how leaders can grow into living a question-led life.

Your life is a reflection of the questions you are asking—of yourself, of God, and of others. And the quality, significance, and depth of your questions determine the quality, significance, and depth of your leadership. Management expert Peter Drucker has argued that “The leader of the past may have been the person who knew how to tell, but certainly the leader of the future will be a person who knows how to ask.” Elsewhere he writes, “The number one difference between a Nobel prize winner and others is not IQ or work ethic, but that they asked bigger questions.” Questions are crucial to engaging with God, with Scripture, with others, and with ourselves.

Small group and Bible study leaders spend time preparing, studying, researching, and organizing their thoughts and notes before the group meets. But how much of that time is spent developing thoughtful, engaging, and incisive questions to ask of others? Here are seven ridiculously practical ways to sharpen our question-asking skills as we prepare to lead:

1. Be aware of the four levels of questions.

Most conversational questions fall into one of four levels of depth. As a leader, it’s important to be aware of these levels and know when, how, where, and with whom to use them. Make sure your groups are clear on expectations and boundaries, as well.

Level 1: simple facts. Questions that are unintimidating and easy to answer, even with strangers.(What is your name? Where do you live? How long have you lived here?)

Level 2: feelings/emotions. Questions that express intention and care and are usually asked when a relationship has already been established (When that happened to you how did that make you feel? On a scale of 1 to 10, how excited are you about this opportunity?)

Level 3: desires/passions. Questions that require more self-disclosure and opening up. These are asked when trust is present, commonly among closer friends or cultivated among small groups. (What do you want—really want—in your life? What breaks your heart? What are you absolutely passionate about? What would you do if you weren’t afraid?)

Level 4: vulnerability/intimacy. Questions that require us to bare our souls, usually with a select few of the most trusted friends. (If crying: what “prayer” is your face praying right now? Can you identify your heart’s cry in this moment? What would you want people to know right now that you might not have ever shared with others?)

Think about the levels like swimming in a lake: ankle deep (Level 1), knee/waist deep (Level 2), chest/neck deep (Level 3), and swimming without touching the bottom of the lake (Level 4). If you ask open-ended questions well, you are giving people a chance to keep it at the current level or to take it deeper. People will only feel comfortable to move naturally to deeper levels if trust is established with you and the group. As leaders, we need the discernment to know which level is the most appropriate in a particular relationship or group.

2. Be curious and inquisitive about the passage.

We have to start with the right mindset when it comes to questions. Andrew Carnegie is credited with saying, “Don’t try to be interesting. Be interested.” Questions draw people out, and similarly being curious and interested can lead to significant breakthrough when engaging with Scripture. Any rabbi will tell you that without questions, it is impossible to discover and explore what the text says. Try writing out two dozen questions you have of the text. Then ask others to jot down several of their own. Cultivate interest, curiosity, wonder, and an inquisitive spirit as you explore God’s Word.

3. Develop or collect a list of ten great questions you can use at any time.

When you come up with significant, engaging, and incisive questions, write them down in an accessible journal or the notes section on your phone. And when you hear others ask a great question, write it down as well. Keep the list handy and don’t be afraid to pull out the questions and use them, especially when you’re feeling stuck.

4. Study people you know who ask great questions.

Think of the people in your life who ask great questions. Ask them if they would be up for a phone call or if you could treat them to lunch or coffee. Pick their brain and ask them how they became great question-askers. Ask them to share advice about asking better questions.

5. When studying the gospels, get a red-letter edition of the Bible and circle every red question mark you find.

Red-letter editions of the Bible mark the words of Jesus in red—including his questions. Every time you see a red question mark circle it, pay close attention to it, and ponder the question Jesus asked. Ask yourself, Why did he ask it? Who was the question directed to? Where did he ask it? What did he expect as a response from his listeners? Explore those Jesus questions together with others as well.

6. Follow up with more questions to keep the conversation going.

When people are sharing their perspectives, especially in a group setting, learn to ask brief follow-up questions to draw them out further. Try Why do you think that? Or why is that? Tell me more. Keep going. Have you always felt this way? or even Is there anything else you want to share? Oftentimes the depth of conversation is found when someone asks a follow-up question in the midst of discussion.

7. Pray for the ability to ask great questions.

Many people want to grow in the ability to ask better questions, but we forget to ask God to teach us. Commit to praying that God would give you the passion and ability to be a great question-asker for his glory. God loves to hear what’s on the heart of his kids. Don’t hesitate to ask the great Question-Asker himself.

Bonus: if you get stuck and still aren’t sure what to do when engaging with Scripture, use these five meta-questions. You can ask these same five questions every time to cultivate wonderfully diverse and vibrant conversations and explorations about Scripture.

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J.R. Briggs
J.R. Briggs

J.R. Briggs started Kairos Partnerships in 2011 where his role is expressed through coaching, consulting, speaking, teaching, equipping and writing to serve a wide variety of leaders, pastors, churches, non-profits, ministries, companies and denominations. Over the past several years, he has invested in kingdom leaders in over 23 states from over 40 different denominations. In addition to starting Kairos Partnerships, he planted The Renew Community, received a master’s degree in Missional Theology at Biblical Theological Seminary, and is currently working on a Doctor of Ministry degree at Biblical. His doctoral thesis focuses on how question-asking in leadership can advance God’s mission. He is an author, co-author and contributed to nine books that seek to equip and care for kingdom leaders. J.R. and his wife Megan have been married for over 16 years and have two sons, Carter and Bennett.

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