Mentors ask great questions. We don’t always know the impact our questions will have until they are heard by the mentee. Often, these great questions emerge from a pool of mentors, perhaps as starters or simply as something to introduce at the right moment.
These questions can also serve you well as you journal—simply writing thoughts, prayers, experiences, questions, memories, in a carefully kept notebook for you to read again. Journaling is a spiritual practice that takes you deep into your inner landscape. Many find it a valuable way to explore fears, dreams, aspirations, and convictions through regular writing.
We’d love for you to keep these questions for spiritual friendship close at hand. That’s why we’ve created a printable PDF of spiritual mentoring questions—a free resource that includes all 25 questions and the first practice prompt. Print it, tuck it into your journal, or bring it to your next mentoring conversation.
25 Great Questions for Spiritual Friendship
- Are you at a crossroads in your life? Can you describe the intersection as you see it?
- What are you afraid to talk about?
- If we were to meet in a year, what would we be celebrating?
- Tell me about a time you adapted well to change. Didn’t adapt well?
- What’s working well in your life right now?
- What’s giving you life (or saving you) right now?
- If the past 5 years were a chapter in your life, how would you entitle that chapter? Why?
- If the next 5 years are a chapter in your life, what is that chapter about?
- Can you be faithful to your spiritual identity in your current career?
- What have you said yes to that you no longer really believe in?
- Have you ever withheld forgiveness from anyone? How about now?
- How did you come to believe in _____________?
- What did your parents want you to be?
- How do you hope to spend the years ahead?
- Isak Denisen said, “All sorrows can be borne if you put them into a story.” Do you have such a story?
- Are you at peace?
- What came into the room with you today?
- Respond to this question: What do you know now that, had you known it 5, 10, or 20 years ago, would have changed your life?
- When you were ten years old, did you know yourself to be a beloved son or daughter?
- When have you seen redemption in your story? How long ago was this?
- When have you experienced pain, sorrow, or grief that just won’t heal?
- If God gave you a name written on a white stone (Revelation 2:17), what might it be?
- Describe your ideal self to a trusted friend: who are you, ideally, as a friend, worker, spouse, parent, sibling, citizen, and follower of Jesus?
- God forms you through pain and brokenness, as well as shalom or wholeness. Can you identify times you were formed by pain? brokenness? shalom?
- Can you name what you uniquely bring to others about the person and character of God by how you live your life?
Practice: Your Best Questions
Take time to identify your own “best questions”—the ones you’ve asked others or been asked yourself. Journal your answer to one of them.
Then, share your question in the comments below so others can benefit from it. Or, if you have a mentor or mentee, bring your best question into your next conversation.
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Keith Anderson, D.Min., is a Faculty Associate for Spirituality and Vocation at VantagePoint3 and President Emeritus of Seattle School of Theology and Psychology. He is the author of several books, including his most recent: On Holy Ground: Your Story of Identity, Belonging and Sacred Purpose (Wipf & Stock, 2024). His other works include Reading Your Life’s Story (IVP, 2016), A Spirituality of Listening (IVP, 2016), and Spiritual Mentoring (IVP, 1999). In his writing, teaching, and mentoring, Keith seeks to set a table for people looking to enter the “amazing inner sanctuary of the soul” in the most ordinary and extraordinary moments of life.
2 Comments
Similar to your #2 in your list, my mentor would often say, “Tell me something you don’t want to tell me.” That’s always when the conversation became real. This level of intimacy in conversation needs the stability and trust in the relationship. I’ve used this in some of my own mentoring relationships but it takes a while to be bold enough to throw this into the conversation. Thanks for this list! You’re a valuable and wise resource to the larger community of faith, Keith! And to the larger VP3 group, you also have become an important resource for the churches we serve in Kansas & Oklahoma. Thanks for regularly posting these thoughts!
Question: If you think God is calling you to grown in _____________, what small, medium and hard steps will you take with Him to grow, when will you start, and who will hold you accountable to do so?