Coaching with the Questions of Jesus

How Thoughtful Questions Help People See Clearly and Move Forward

Questions as a Form of Care

Some of the conversations that shaped me most did not begin with advice. They began with a question.

My friend and mentor Paul Stanley knew how to ask a thoughtful question and then remain quiet long enough for me to hear my own answer. He did not ask one question and hurry on to the next subject. He listened carefully, stayed with what I was saying, and often followed the thread with another question.

Paul gave me plenty of counsel. He shared what he had learned from his own life and helped me avoid mistakes he had already made. Yet he never tried to make me into another version of himself. His questions helped me recognize how God had formed me, what I was learning, what I needed to face, and what might be possible.

Paul also helped me learn from what I had lived. Experience by itself does not necessarily make us wiser. We have to stop long enough to consider what happened, what it revealed about God and ourselves, what we might do differently, and what wisdom we should carry forward.

Because Paul listened that way, I felt known, valued, and believed in. Only later did I understand how intentional Paul had been in mentoring, coaching, and developing me. His questions had become a form of care.

Why Questions Matter

The value of a thoughtful question can appear in very different settings. During a difficult season at Intel, the company’s memory-chip business was losing ground, and its leaders had been unable to agree on a clear direction. Andy Grove asked Intel co-founder Gordon Moore to imagine that the two of them had been replaced. What would a new chief executive do? Moore answered that a new leader would take Intel out of the memory business. That allowed Grove to ask the question they had been avoiding: If that was what new leadership would do, why shouldn’t they make the decision themselves? Intel eventually left the memory-chip business and focused on microprocessors, a decision that helped redefine the company.

The question did not make their decision easy. It helped them acknowledge what they already knew but had been reluctant to act upon. A thoughtful question can bring into words what we sense but have hesitated to face. It can cut through the noise, reveal what matters, and help us take responsibility for what comes next.

When I use the word coaching in this resource, I mean helping another person think more clearly, recognize possibilities, and take greater ownership of the next step. Spiritual coaching gives particular attention to what God may be doing and how the person might respond. Yet the practice of asking good questions reaches far beyond a formal coaching relationship. It can serve us in mentoring, leadership, discipleship, friendship, parenting, and ordinary conversations around a kitchen table.

Questions are only one way we care for people. A mentor may need to share wisdom. A leader may need to make a decision or provide direction. A parent may need to establish a boundary. A friend may need to speak honestly. Good questions do not remove those responsibilities. They help us understand the person and the situation before deciding what we have to offer.

How Jesus Used Questions

Jesus was not a coach in the modern sense, and He understood the human heart in a way we never will. He did not ask questions because He lacked information. He taught with authority, comforted, corrected, confronted, and gave clear direction. He is the Truth, and His questions were never a substitute for truth. They were one of the ways He brought people into an honest encounter with it.

When we read the Gospels, we find Jesus asking questions in many different settings. Some were gentle. Others were direct and uncomfortable. Almost all of them reached beneath the surface.

Questions That Clarify What We Believe and Trust

“Who do you say I am?”Matthew 16:15 NIV

“Where is your faith?”Luke 8:25 NIV

Jesus moved the conversation beyond what other people believed. He asked for a personal response. Who do you believe I am? Can you trust Me here?

Questions like these bring belief out of the abstract and into the circumstances we are actually facing. They can help us recognize the distance between what we say we believe and the way we are responding. They may also uncover where fear has displaced trust or why a familiar pattern keeps returning.

Questions That Reveal What Is Happening Within Us

“What do you want me to do for you?”Mark 10:51 NIV

“Why do you entertain evil thoughts in your hearts?”Matthew 9:4 NIV

Jesus did not deal only with outward behavior. He invited people to name their desires and face what was happening within them.

Our first answer is not always our deepest one. What we say we want may be different from what we are willing to pursue, receive, or change. Our choices may also be shaped by motives we have not fully examined, including fear, pride, ambition, judgment, insecurity, or self-protection. A thoughtful question can help bring those things into the light without immediately accusing or condemning the person.

Questions That Open Our Eyes to God’s Activity

“What are you discussing together as you walk along?”Luke 24:17 NIV

“Why are you troubled, and why do doubts rise in your minds?”Luke 24:38 NIV

On the road to Emmaus, Jesus entered the disciples’ disappointment with a question and allowed them to tell their story. Later, when He appeared to the gathered disciples, He named their trouble and doubt. God is often at work before we recognize what He is doing. A good question can help someone slow down, revisit what has happened, and notice what may have been missed. It can also help a person distinguish between what they fear, what they assume, and what may actually be true.

Questions That Call for a Response

“You do not want to leave too, do you?”John 6:67 NIV

“Do you love me?”John 21:15 NIV

Some questions bring us to a point of decision. They move the conversation from reflection to response.

Jesus did not force people to follow Him. He made the invitation clear and allowed them to choose. After Peter’s failure, Jesus’ question also opened a way toward restoration and renewed responsibility. His questions called for personal ownership. They remind us that insight cannot remain theoretical. Eventually, it must shape the way we live.

Across these encounters, Jesus was not merely collecting answers. He was helping people name reality, recognize what was happening within them, notice God’s activity, and decide how they would respond. His questions show us that truth and care belong together.

A Simple Way to Guide the Conversation

Good conversations are rarely as orderly as we might prefer. Still, over the years I have found it helpful to keep six movements in mind:

1. Clarity→
2. Awareness→
3. Possibilities→
4. Discernment→
5. Action→
6. Accountability

These movements are not a formula or an attempt to reduce Jesus’ conversations to a method. They simply help me listen for what may be needed next. Not every conversation will move through all six areas, and the order may change. Sometimes one thoughtful question is enough.

1. Clarity—What Is Really Going On?

Most people begin with the part of the story they can see most easily. As I listen, I am trying to understand what truly needs attention rather than hurrying toward a solution. A concern about a difficult coworker may eventually reveal fear about the future, disappointment over something that happened, or uncertainty about a decision. Questions such as “What would be most helpful for us to talk about?” or “What seems most important beneath all of this?” can help bring the real issue into view.

2. Awareness—What Is Happening Within You?

Once the concern is clearer, I want to help the person notice what is happening within them. What are they thinking and feeling? What assumptions are shaping their response? Are there repeated patterns, unspoken desires, gifts, fears, or tensions they have not yet recognized? In a spiritual conversation, I may also ask where they sense God at work. We cannot take responsibility for something we have not yet been willing or able to see.

3. Possibilities—What Else Might Be Possible?

When we feel stuck, our world can become very narrow. It may seem as though we have only one or two choices, neither of them very hopeful. A thoughtful question can create room to see something more: What else could you do? Who might help? What strength or resource have you not yet considered? The purpose is not to produce an endless list of options. It is to loosen the hold of the first answer—and sometimes the most fearful answer—so that a better way forward can emerge.

4. Discernment—What Seems Wise and Faithful?

Possibilities alone are not enough; eventually, they must be weighed. Which path is consistent with the person’s values, responsibilities, calling, and present season? What are the likely consequences? What light does Scripture bring? What might God be doing, and what do trusted people see? Discernment helps us move beyond what is merely possible or personally appealing toward what is wise and faithful.

5. Action—What Will You Do?

At some point, insight needs to become a response. The next step may be quite small: begin a conversation, gather more information, make a decision, offer an apology, practice a different response, or stop avoiding something that needs to be faced. Whatever the step may be, it should be clear enough for the person to express in their own words and genuinely own. We are not assigning a task; we are helping someone choose a responsible way forward.

6. Accountability—What Will Help You Follow Through?

Good intentions can disappear when life becomes busy. Accountability provides agreed-upon support for doing what a person has chosen to do. When will they act? What might get in the way? Who else needs to know? When will you return to the conversation? Accountability is not control. At its best, it is a simple expression of care that helps intention become commitment.

Asking Questions Wisely

When Questions Are Not Enough

Questions are one way of helping people, but they are not the answer to every situation. Jesus asked penetrating questions, and He also taught, corrected, challenged, comforted, and gave clear direction. We need similar discernment.

A leader should not use questions to avoid a decision that belongs to them. A parent should not turn a necessary boundary into a conversation with no conclusion. A mentor should not withhold wisdom that could genuinely help. There are times when encouragement, correction, or difficult truth needs to be offered plainly and graciously.

Coaching also has limits. It can help someone think through a concern, but it is not a substitute for professional counseling or other specialized care. When a need goes beyond our experience or responsibility, part of caring well is helping the person find the right support.

Ask Less and Listen Longer

Ask one question at a time, and give the person room to answer it. Several questions strung together can feel overwhelming and may reveal that we are doing more thinking than listening. Silence is not necessarily a problem. People sometimes need a little time to hear their own thoughts before they can put them into words.

Keep Questions Short and Open

Simple questions usually create the most room:

“Tell me more.”

“What makes that important to you?”

“What do you think is beneath that?”

Questions beginning with what or how often invite reflection more naturally than questions that can be answered with yes or no. Even a question beginning with why can be helpful when it is asked with warmth rather than accusation.

Follow the Person’s Words

Listen for the words a person chooses, especially anything they repeat. Notice changes in tone, pace, emotion, or hesitation. Those moments may point toward something worth exploring.

Sometimes reflecting what we hear is more helpful than immediately asking another question:

“I hear both excitement and hesitation. What do you think is creating that tension?”

Know When It Is Time to Speak

A conversation should not feel like an interrogation. Sometimes the most helpful response is empathy, encouragement, truth, or simply remaining present.

When I have an observation or experience that may be useful, I often ask:

“Would it be helpful if I shared something I have noticed?”

After sharing it briefly, I can return ownership to the other person:

“What do you make of that?”

The deeper work is not mastering a questioning technique. It is becoming more attentive to the person, the situation, and what God may be doing.

Common Pitfalls

Even with good intentions, several habits can limit the value of a conversation:

The purpose of a question is not to demonstrate our skill. It is to serve the person in front of us.

Closing Reflection

The questions Jesus asked have not lost their power. They still reach us in the quiet places of our own lives:

“Who do you say I am?”Matthew 16:15 NIV

“What do you want me to do for you?”Mark 10:51 NIV

“Why are you so afraid?”Matthew 8:26 NIV

“Do you love me?”John 21:15 NIV

These are not questions we answer only once. We continue answering them through the choices we make, the relationships we cultivate, and the way we live.

When we walk with others, our task is not to impress them with our answers. It is to listen well enough, care deeply enough, and ask the question that helps them see what is true and decide how to respond.

The right question, asked with genuine care, can help open a life.

Appendix: Questions to Help People Grow

These questions are starting places, not a checklist. Choose one or two that fit the person, the relationship, and the situation. A conversation may not move through all six areas, and the order may change. Listen for the question that may help most.

Clarity—What Is Really Going On?

• What would be most helpful for us to talk about today?
• As you think about it now, what seems to be the real issue?
• What have you tried so far, and what happened?
• What would make this conversation useful?

Awareness—What Is Happening Within You?

• What are you noticing in yourself as you talk about this?
• What do you really want?
• What fear, assumption, or familiar pattern may be shaping your response?
• Where might God already be at work?

Possibilities—What Options Do You See?

• What options do you see right now?
• What might you consider if fear were not shaping the decision?
• What strengths, relationships, or resources could you draw upon?
• Who might help you see a possibility you have missed?

Discernment—What Matters Most?

• What matters most here?
• Which possibility seems wisest, and why?
• What is most consistent with Scripture and the responsibilities God has given you?
• What do you sense God may be inviting you to do?

Action—What Will You Do?

• What is the next practical step?
• What part of this is yours to do?
• What preparation will that require?
• What could get in the way, and how will you respond?

Accountability—How Will You Follow Through?

• When will you take the next step?
• Who could support or encourage you?
• What will you do if you become stuck?
• When should we revisit your progress?

Source Note

The account of Andy Grove and Gordon Moore is paraphrased from Andrew S. Grove, Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company and Career (New York: Currency Doubleday, 1996), 89.

My understanding of evaluated experience and the formative power of thoughtful questions was deeply influenced by my mentor, Paul Stanley. The six-movement pathway presented in this resource grew from my years of coaching, mentoring, and leadership conversations.