Book: The Discipleship Blueprint – Chapter 12: The Art of the Ask
- Dr. Layne McDonald
- Jun 9
- 7 min read
“The purposes of a person’s heart are deep waters, but one who has insight draws them out.” , Proverbs 20:5 (NIV)
Most mentors think their job is to have all the answers. They believe that to be a spiritual guide, they must be a walking encyclopedia of theology, a fountain of perpetual wisdom, and a tireless dispenser of "the right advice." But if you look at the life of Jesus, the greatest mentor the world has ever known, you see a very different pattern.
Jesus didn’t lead with answers; He led with questions.
Out of the 307 questions Jesus was asked in the Gospels, He only answered three directly. Conversely, He asked 307 questions Himself. Think about that for a moment. The Son of God, who held the mysteries of the universe in His hands and the secrets of the human soul in His gaze, chose to ask more than He chose to tell. Why? Because an answer provides information, but a question facilitates transformation.
In Chapter 12, we are stepping into the holy ground of intentional mentoring: The Art of the Ask. We are learning how to become like the one Proverbs 20:5 describes, the one who has the insight to draw out the deep waters of another person’s heart.
The Master’s Method: Jesus and the Question
To understand why questions are the primary tool for spiritual growth, we must look at how Jesus used them. He didn’t use questions to gain information; He didn’t need to (John 2:25). He used them to create a collision between the human heart and Divine Truth.
When Jesus stood with His disciples and asked, "Who do people say the Son of Man is?" and then followed it with the piercing, "But what about you? Who do you say I am?" (Matthew 16:13-15), He wasn’t conducting a Gallup poll. He was forcing Peter to give voice to a conviction that would change the course of history.
Questions bypass our defensive walls. They invite us to own our beliefs, confront our fears, and articulate our internal world. When we tell a mentee what to do, we are giving them a map. When we ask them a Spirit-led question, we are giving them the opportunity to walk the path themselves.
Why We Struggle to Ask the Hard Questions
If the art of the ask is so powerful, why is it so rare in our churches and mentoring relationships? Why do we default to "advice-giving" or surface-level "How are you doing?" pleasantries?
The Fix-It Reflex: We hate to see people in pain or confusion. Our natural instinct is to jump in and "fix" the problem so they feel better (and we feel more competent).
The Fear of Silence: Deep questions often lead to long pauses. In our fast-paced culture, we view silence as awkward or unproductive. In discipleship, silence is often the sound of the Holy Spirit working.
Lack of Discernment: We haven't trained our spiritual "ears" to listen for what is not being said. We stay in the shallows because the deep waters require more effort to navigate.
The Desire for Authority: It feels good to be the "expert." Asking a question requires us to lay down our status as the one with the answers and become a co-traveler on the journey.
To be a blueprint mentor, you must die to your "Fix-It" reflex. You must realize that your primary goal is not to solve a problem, but to foster a relationship between the mentee and the Holy Spirit.
The Anatomy of a Transformational Question
Not all questions are created equal. In the world of Christian coaching and intentional mentoring, we distinguish between questions that close doors and questions that open hearts.
If you want to move into deep discipleship, you must master the shift from Closed Questions to Open Questions.
A closed question can be answered with a "yes," a "no," or a single fact. It puts the mentor in the driver's seat and limits the mentee’s reflection. An open question, however, requires the mentee to look inward, process their emotions, and explore their motivations.
Examples of the Shift:
Spirit-Led Discernment: The "Nudge" of the Holy Spirit
As an Assemblies of God-aligned mentor, you must believe that the Holy Spirit is the true Teacher (John 14:26). The "Art of the Ask" is not just a psychological trick; it is a spiritual discipline. It requires you to listen with two sets of ears: one for the mentee’s words, and one for the Spirit’s promptings.
I call this "Dynamic Discernment." While the mentee is speaking, you are asking the Lord: “Father, where are You working right now? What is the root issue here? What is the one question that will unlock this door?”
Often, the Spirit will give you a "holy nudge." You might feel a prompt to ask about a seemingly unrelated childhood memory, a specific fear, or a recurring pattern of behavior. When you follow that nudge, you are no longer just having a conversation, you are participating in a divine encounter.
The 4 Layers of a Deep Question
When I train mentors, I encourage them to visualize the heart as having four layers. Your questions should aim to penetrate each one:
The Surface Layer (Behavior): "What happened?"
The Emotional Layer (Feeling): "How did that make you feel?"
The Root Layer (Belief): "What do you believe about yourself or God in that moment?"
The Surrender Layer (Action): "How is Jesus inviting you to trust Him in this?"
Most mentoring stays at Layer 1 or 2. Transformation happens at Layer 3 and 4. You cannot get to Layer 4 without the bravery to ask the questions that make Layer 3 visible.
Practical Toolkit: 20 Questions for Transformation
Here is a resource you can use in your next mentoring session. These are not a script, but a starting point for drawing out the "deep waters."
If you could change one thing about your spiritual life right now, what would it be?
What is the most frequent "lie" you find yourself believing during the day?
When do you feel most "alive" in your walk with God?
Where is the "friction" in your life right now? What do you think God is trying to teach you through it?
What are you currently avoiding?
If Jesus were sitting in that empty chair next to us, what do you think He would want to say to you about your current situation?
What is the "shadow" in your success right now?
Whose approval are you most afraid of losing?
When you think about the future, do you feel more fear or more hope? Why?
What part of your story are you still trying to hide from God?
How is your current pace of life affecting your intimacy with Christ?
What was the last thing God clearly asked you to do? Did you do it?
What "old habit" is trying to make a comeback in your life?
If you had to describe your current season of life in one word, what would it be?
What are you most grateful for that you haven't thanked God for yet?
Who are you currently discipling, and what are you learning from them?
What is the biggest barrier between you and total surrender?
How are you stewarding the gifts God has given you in this season?
What would your life look like if you truly believed you were fully loved by the Father?
What is the one thing you need to lay at the feet of Jesus before you leave this room?
The Ethics of the Ask: Grace, Not Interrogation
A word of caution: The power to ask deep questions must always be balanced with the heart of a servant. We are not prosecuting attorneys; we are spiritual surgeons.
If you ask a hard question without building a foundation of trust (which we covered in Chapter 11: The Architecture of Trust), the mentee will feel exposed and attacked. The "Art of the Ask" must be wrapped in the "Spirit of Grace."
Always give the mentee permission to "not go there" yet. Respect their boundaries. If you sense a wall going up, don't kick it down. Ask: "I sense that this is a difficult area to talk about. Is this something you feel ready to explore today, or do we need more time?" This gives them the power and ensures the mentoring relationship remains a place of safety.
Conclusion: The Gift of Being Seen
When you ask a transformational question, you are giving your mentee one of the greatest gifts a human can receive: the gift of being truly seen and heard.
Most people live their lives in a fog of unexamined thoughts and unvoiced fears. By asking the right questions, you help them clear the fog. You help them see what the Holy Spirit is doing. You help them take the next step toward the likeness of Christ.
Start today. In your next conversation, whether with a formal mentee, a spouse, or a child, stop yourself from giving advice for the first ten minutes. Instead, try to ask three open-ended, Spirit-led questions. See what the Lord draws out of those deep waters.
Takeaway Action Step: Choose three questions from the "Practical Toolkit" above. Spend time in prayer asking the Holy Spirit which one He wants you to ask yourself first, and then which one you should bring to your next mentoring meeting.
What if the very answer your mentee has been searching for is already inside them, just waiting for the right question to unlock the door?
About Layne McDonald, Ph.D. Dr. Layne McDonald is a dedicated author, leader, and mentor with a passion for helping individuals and organizations align their lives with biblical truth. With dual Ph.D.s and decades of experience in ministry and executive leadership, Dr. McDonald specializes in creating resources that foster spiritual maturity, cultural discernment, and heart-centered leadership. His work is rooted in the authority of Scripture and the transformative power of the Holy Spirit, aiming to guide every reader toward a deeper relationship with Jesus Christ and a life of eternal purpose.
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