Ask good questions.


Learn how to listen, ask questions, and guide a conversation that helps people to learn, grow, and discover for themselves.

A good question can literally change someone’s life. Dr. Joseph Umidi, on whose work much of this training is based, tells a story about a time when during the course of a 25 minute conversation a man he had never met before asked him five questions that changed his life.

One of the questions was, “If you keep doing the things you’ve been doing for the last five years, where will your life be in the next five years?” It caused him to re-evaluate what he was doing and where he was going and ultimately resulted in a major course change in his life.

In this training we will explore how you can ask questions that have a radical impact on the members of your small group.


  • Assignment 1 // Read Matthew 16:13-16 & Answer Questions

  • Assignment 2 // Read Listening for What Really Matters & Answer Questions

  • Assignment 3 // Read The Best Questions & Answer Questions

  • Assignment 4 // Practice Asking Good Questions


Matthew 16:13-16 (ESV)

Now when Jesus came into the district of Caesarea Philippi, he asked his disciples, “Who do people say that the Son of Man is?” And they said, “Some say John the Baptist, others say Elijah, and others Jeremiah or one of the prophets.” He said to them, “But who do you say that I am?” Simon Peter replied, “You are the Christ, the Son of the living God.”

This was the first time that one of Jesus twelve closest followers unequivocally declared that Jesus was the the Messiah (Christ), the savior who had been promised.

When Jesus began his public ministry and invited people to follow Him, He didn’t sit down with each of them and work through a point by point proof that he was the savior that they were expecting. They followed Jesus because he was a teacher, a rabbi, because they knew there was something special about Him, but they didn’t necessarily know who He truly was. He invited them to come and see, to explore and learn for themselves.

By the time Jesus asks these followers who they believed he was, they had been following him for awhile. He could have simply said, “I am the Christ, the Son of the living God,” but by asking the question, it forces them to make a choice, to crystalize in their own minds what they believe about Him.

There’s something powerful that happens when people figure something out for themselves. The journey to discovery is as important as the discovery itself. That journey is the difference between a true, fully-orbed understanding and the comparatively superficial knowledge that comes from learning something from a book.

The Inca Trail begins near Cusco, Peru, the ancient capital of the Incan empire, and is the route that the Incans used to get from Cusco to Machu Picchu, an unbelievable city built into the side of a mountain. Machu Picchu is a masterpiece of engineering, especially for the 15th century, and it’s an incredible place to explore. But key to the experience is the journey that it takes to get there.

To get to Machu Picchu, travelers hike the Inca Trail. It’s a hard but not undoable four day hike during which you ascend up a mountain to nearly 14,000 feet, where you hike through the cool, thin air at Dead Woman’s Pass. On the fourth day you get up extra early to arrive at sunrise and look out over Machu Picchu from the sun gate before descending to explore the city.

Or, you can take the train to a bus that will take you up to look around.

If Jesus had tried to explain who He was up front to the people He invited to follow Him—or later just told them that the was the Messiah—they could have simply thought to themselves, “Ok, maybe… we’ll take that into consideration and keep thinking about it.” Rather, Jesus asked them a question that forced them to articulate for themselves what they believed.


  1. What is one experience you’ve had that has shaped you in a way that simple book-learning could not have replicated?


Key to being able to ask good questions is listening to the person or persons with whom you are dialoguing. There are three levels of listening:

Level 1: Self-focused listening

Self-focused listening is, just as the name indicates, all about the listener. When practicing level 1 listening, questions like “What does this mean to me?” and “How will this impact my life?” are running through the listener’s head. The focus is on the listener and how what is being communicated impacts him/her.

Level 2: Others-focused listening

Others-focused listening is about the speaker. When practicing level 2 listening, questions like “What does this mean to this person?” are running  through the listener’s head. The focus is on the speaker and what he or she is communicating.

Level 3: Purpose-focused listening

Purpose-focused listening is still about the speaker, but it’s listening for what is really happening below the surface. Questions like "What does this really mean?" and “What would cause the speaker to respond in this way?” are in the listener’s head. The focus is not only on the other person but also on the underlying meaning and significance of what is happening.

Obviously Level 1 listening is a terrible basis for developing questions that will help people learn, grow, and discover for themselves. If someone tells you they’re struggling to find a job and all you’re thinking is, “I hope they don’t ask me for money,” you’re not likely to ask them any questions that help them deal with the situation they’re in.

Level 2 listening is clearly better. In the above scenario, if you’re practicing level 2 listening, you’re concerned about the person and his or her situation. You might ask questions like, “What can I do to help you find a job?”

Those aren’t bad, but level 3 listening will allow you to help the person figure out what it is he or she really needs to navigate the situation. With level 3 listening, you’re looking for what’s below the surface. You’re trying to figure out the why behind the what. You might ask a question like, “What has made it so difficult for you to find a job?”

Now we’re getting somewhere. Maybe the person says that when they apply they’re told they don’t have enough education. So then you follow up with, “What would it take for you to get the additional education you need?” You can see where the question you asked when practicing level 2 listening wasn’t bad—you were clearly concerned about the person and their situation—but it also wasn’t the most helpful.

The likely response to the question, “What can I do to help…” is something like, “If you hear of any openings in my field, let me know.” But if the person doesn’t have the needed education, while you might be able to help them find a job if you’re good friends with a hiring manager, you probably can’t, especially if that hiring manager friend doesn’t owe you a big favor. Hiring someone who doesn’t have the qualifications for a position is no small thing. And either way, what happens when that person needs to change jobs again?

But with the level 3 question you’re able to get at the root cause of the person’s inability to find a job and begin helping him or her think through how to deal with it.

Notice that in this scenario, you didn’t have any answers for the person. You didn’t solve his or her problem. You didn’t even figure out the solution. You simply asked questions that caused the other person to come up with solutions. Intuition Indicators Level 2 and especially level 3 listening requires looking out for intuition indicators, key markers that will help identify underlying issues. They include:

  • A person's own discernment - Is there anything the person has already figured out that maybe they just don’t realize? Look for statements like, “I know that ultimately I need to get more education to have the job I want, but school is so expensive.” He or she knows what to do but needs help figuring out the how.
  • Patterns and fruit - Listen for recurring themes or results in what the speaker is telling you. If the speaker mentions that he or she has been laid off twice before, you might ask a question like, “You’ve mentioned you’ve been laid off three times, is there common thread that runs through these that might help explain why?”
  • Strong emotions or reactions - Perhaps the speaker angrily responds to your question with, “All of my bosses have been terrible people!” Often when people respond with an intense emotion, there’s something more going on. Maybe they had a particularly damaging relationship with a boss that has colored their relationship with their other bosses. Maybe their bosses have been fine and they simply don’t like authority. Ask questions like, “What are some specific experiences that made you dislike them so much?” And then you might ask follow-up questions about how the boss might have felt in that situation to help them see the other side.
  • History items - This is something in someone’s past that might be impacting their present situation. Maybe they state that they didn’t have a very good relationship with their parents and then later mention they struggle relating to their bosses. It’s possible that the problems with their parents are coloring their interactions with their bosses. You might ask, “What do you think makes it difficult to relate to your bosses?”
  • Confirmation and counsel - What advice or perspective has the speaker gotten from other trusted friends or advisors? Listen for things like, “My last boss encouraged me to…” “My mom said I should…” The speaker may need you to ask questions that help analyze and evaluate the advice already given.
  • Red flags - This could be anything that raises a level of concern in your mind.
    • Someone being laid off three times is a red flag.
    • If the person seems intent on ignoring the good advice others have given, that’s a red flag. You: Do you see any merit in that advice?
    • Maybe the speaker has an unrealistic view of his or her employability or the salary he or she can expect to make. You: Have you done any research on what folks in similar positions make?
    • Perhaps the person mentions doing something unethical or illegal to land a job. You: You mentioned doing _____ to get a job. What do you expect will result from that?


  1. What level of listening do you tend to default to? What can you do to move up a level?


Open Ended Questions

The best questions are open-ended questions, questions that invite dialogue or provoke thought rather than simply have a correct answer. Close-ended questions don’t tend to invite much self-discovery or sharing.

Closed: Where did you go to college?

Open: What made you decide to go to college?

Closed: What does John 11:32-36 say was Jesus’ response to Lazarus’ death?

Open: What does John 11:32-36 teach us about Jesus?

Closed: Do you want to find a job in the tech field?

Open: What type of work are you interested in doing?

Leading Questions

Leading questions and advice-giving can kill dialogue. Sometimes as leaders we need to give advice or to ask leading questions, especially when the person isn’t seeming to come to something on their own. But ideally, and to begin, we want to ask questions that help people figure things out or themselves. Only after exhausting the productivity of asking truly open questions should we ask leading questions.

Leading: What does this passage teach us about how much God loves us?

Translation: God loves us a lot!

Open: What can we learn from this passage about God’s character?

Leading: Are you concerned about the potential repercussions of your actions?

Translation: There will be repercussions if you do that!

Open: What do you think the possible outcomes are?

Powerful Questions

The best questions are also powerful questions. You can ask open questions that are okay at creating dialogue but aren’t likely to have the impact that a powerful question will have?

Consider the question asked of Dr. Umidi that we referenced earlier, “If you keep  doing the things you’ve been doing for the last five years, where will your life be in the next five years?” That’s a powerful question. “Where do you see yourself in five years?” and “How would you like to see your career develop?” are fine, open-ended questions. But by getting people to evaluate not only what they out of life but how their current actions are impacting where they’re going, the question is far more powerful.

We all know that if you want something different than what you have now, you have to change what you’re doing. But so few of us actually make those changes. This question forces the people to think through what needs to change now to get the desired result, not just to daydream about the desired result. Here are four characteristics that can help make a question powerful:

  • Believing in people

Good: What impact would it have on your family if you were able to accomplish your goal?

Better: What impact will accomplishing your goal have on your family?

  • Leveraging motivation

Good: What impact will this have on your life?

Better: How will this help you achieve your dream of running your own company?

  • Empowering others to take responsibility

Good: What would help solve this problem?

Better: How can you help solve this problem?

  • Recognizing uniqueness

Good: What advice would you give to someone looking to advance in your company?

Better: Based on what you know about Sally’s skills, interests, and experience, what advice would you give her to help her advance in your company?


  1. Write down three examples of powerful, open questions that you might be able touse at work, with your family/friends, or in your small group:


It’s great to read about asking good questions, but the best way to get better at it is to practice. Pair up with someone else from the group and practice asking good questions of each other. Depending on your schedules, you can either do this in-person or on the phone.

You will take turns playing the roles of speaker and listener. The listener will begin by asking the speaker the question, “What is one challenge you are currently facing?” The speaker may respond with something huge and personal or with something smaller. It’s totally up to the speaker to set the level of the conversation.

The listener should focus on asking open, powerful questions. He or she cannot give advice and should not ask leading questions.

After 10 minutes, spend 3-5 minutes debriefing the conversation. The speaker should give the listener feedback on which questions were especially helpful and let the listener know if they felt any questions were leading or were otherwise unhelpful.

Then, switch roles and repeat the process. During the session, record notes/thoughts/comments.


If this content intrigues you and you’d like to explore it further, check out Dr. Joseph Umidi’s online course, “Real Talk: When Ordinary Conversations Become Extraordinary.”

LEADERSHIP TAKEAWAY (To be completed during group discussion)

*(1) Listening levels and intuition indicators adapted from the work of Dr. Joseph Umidi.

*(2)  Question types adapted from the work of Dr. Joseph Umidi.