Practice #2: Asking Good Questions

Written by on February 9, 2018

This week I want to highlight the second of three primary practices that give shape to walking well with others as a friend or a mentor. Last week I addressed the practice of listening, this week question-asking, and next week prayerfulness. My reflections here are again adapted from our VP3 resource entitled Walking Alongside Others: A Mentoring Guide. 

Practice #2: Question Asking

If listening is about presence and attentiveness to another, question asking is about a genuine interest in the other. Good questions reflect a real caring for the person—what is it like to be in their shoes? How are they making sense of their lives? As we learn to walk compassionately with others we discover that people more often need honest and caring inquiry rather than advice or input.

Educator Parker Palmer underscores the importance of asking honest, open questions in our companionship with others. He writes,

Many people, including me, have trouble framing questions that are not advice in disguise. “Have you thought about seeing a therapist?” is not an honest, open question! A question like that serves my needs, not yours, pressing you toward my version of your problem and its solution instead of evoking your truth….

What are the marks of an honest, open question? An honest question is one I can ask without possibly being able to say to myself, “I know the right answer to this question, and I sure hope you give it to me”—which is, of course, what I am doing when I ask you about seeing a therapist….

An open question is one that expands rather than restricts your arena of exploration, one that does not push or even nudge you toward a particular way of framing a situation. (A Hidden Wholeness, 132)

Good questions seek to uncover what is happening in a person’s life and story. Consider your time together like a great exploration—as standing before a great expanse, a mountain range, an ocean, a jungle; rather than as standing over a map. Pay attention to how this individual’s story all fits into God’s larger storyWhat might God actually be up to?  

You will likely be drawn to one or two questions that will help you develop a rhythm in your mentoring sessions:

  • Tell me something good about your week and something that has been difficult.
  • What has become clear to you since we last met?
  • What are you praying about these days?
  • Where in your life have you been feeling most alive? Most drained?
  • What are you thankful for?
  • Whom do you need to forgive?
  • How’s your soul? Or, how’s your heart?

Being comfortable with doubt, confusion, exploration, wonder, and silence will create space for the Holy Spirit to show up. Your questions should not be approached like a checklist. Rather, they must grow out of genuine interest in the other person. Allowing space for thought then acknowledging the answers that come—this will foster an atmosphere of growth. Follow-up questions such as these will invite further thought and discussion:

  • Tell me more.
  • How did that make you feel?
  • What are you finding yourself saying to yourself right now?

Practicing the art of asking open, inviting questions can help us all grow in our capacity to make space for others as they explore and mature into what God is graciously up to in their lives. 

Simone Weil captured the heart of what good questions reflect when she wrote:

The love of neighbor in all its fullness simply means being able to say to him: “What are you going through?”

May we continue to learn to be such neighbors, friends, and mentors… In Jesus’ name. 


I highly recommend Walking Alongside Others: A Mentoring Guide as a resource that could be both  fairly quickly mined for lists of practical, open-ended questions as well as provide a more leisurely, devotional immersion in the attitudes and applications needed to walk compassionately and insightfully with others. We all need help in personalizing these practices for who we are as friends and mentors. And this small book will be of great help in that regard. 


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