Sean McDowell | May 11, 2022

The Key to Asking Great Questions

Bob Tiede is one of the best leaders I know. He was the CEO of Josh McDowell Ministry, and thus worked closely with my father for 24 years (1979-2003). He now leads a ministry called Leading with Questions, which I follow closely. More than anyone, he has taught me the value of asking questions for ministry and relationships. He has a new book out on the questions of Paul, which you can download for free. Check out our conversation and think about downloading 262 Questions Paul the Apostle of Christ asked.

SEAN MCDOWELL: Why are questions such a powerful way to engage people in spiritual conversations?

BOB TIEDE: My friend Andrew Sobel says, “Telling creates resistance! Asking creates relationships!” This quote from David Augsburger hangs on the wall in my office, “Being heard is so close to being loved that for the average person, they are almost indistinguishable.”

Not only spiritual conversations—but all meaningful conversations—have to begin with us being interested in the other person!

When we start by asking questions—and then carefully listening—a new relationship starts! People feel valued! And now we have created the opportunity for a potentially meaningful spiritual conversation.

Sean: You wrote a great book that compiles all the questions of Jesus. What did you learn from studying his questions?

Bob: For all of us who would like to improve our communications skills we would do well to study the communication practices of Jesus! I frequently ask audiences, “What did Jesus’s communication focus on?” They almost always come up with the correct answer: “He told great stories and asked great questions!”

I ask a lot of questions because I don’t know the answers. Jesus being God never asked a question to which he did not already know the answer. So why did he ask so many questions?

The title of that book is, 339 Questions Jesus Asked. When you add up all the questions recorded by Matthew, Mark, Luke and John in the New International Version of the Bible—you come up with 339 questions!

Several years ago, this thought occurred to me, the Scriptures teach that Jesus was involved in Creation. Therefore, might Jesus—who created the brain—understand exactly how it works? Might it be when Jesus asks a question, he is actually leveraging the design of the brain he created? Might he have known that asking questions was a far more effective way to connect with people, to engage people, to help them discover truth, than telling them what they should believe? Might Jesus have known that if he asked someone a question—they would own their answer and that their answer had the potential to change them? Might Jesus have known that asking would be far more effective than telling? Yes! Yes! Yes! Yes! & Yes!

Sean: When you are in spiritual conversations, what are some of your favorite questions to ask people?

Bob: Two of my favorite questions to start almost any conversation with someone I am just getting to know are:

What is your story?

What would you say are the 3-4 events that have most shaped your life?

And then I frequently will ask second and third questions about something they share in their answers.

The result is that by asking and listening they will feel valued and almost always a new relationship has started. With that foundation there is frequently the possibility of asking spiritual questions.

Here is a question that I have started to use that comes from Jon and Paim Strain in her book You Gotta Ask, "Assuming there is a God, and you could ask God anything, what would you ask?" No one I have ever asked this question of has even been asked this question before, so you have to give them time to think. When I asked a waitress she said, "Wow, I am going to think about that one. She left my table but came back about 5 minutes later and shared her answer. And of course, the answers you hear will again open the door for second and third questions.

Sean: You have a new book out on the questions of the Apostle Paul. What did you learn by studying his questions? How are they similar or different from the questions of Jesus?

Bob: The main difference is the questions Jesus asked—recorded by Matthew, Mark, Luke, and John—are questions recorded from conversations Jesus had with people. Whereas, with the exception of the questions recorded by Luke in the Book of Acts, all of Paul’s questions were part of the letters he wrote to the New Testament Churches he had planted. They were questions within the letters he wrote, not part of spoken conversations. Paul used questions in his letters as a way to get his readers to think. After asking a question, Paul shared the answers to most of the questions he wrote.

My past experience in reading and studying Paul’s letters is that when I read a question from Paul, I simply continued reading to see Paul’s answer. In 262 Questions Paul the Apostle of Christ Asked, we only shared Paul’s questions and none of his answers. Obviously, you can open your Bible and find Paul’s answers, but I am encouraging people to not instantly do this. Instead, imagine you are sitting with Paul, and he asks you a question. Take time to think how you would answer before you open your Bible to see how Paul answered. I am guessing that when Paul did ask questions he would wait for their answers before continuing!

Sean: What else would you like to tell us about your new book?

Bob: Three things may be helpful:

First, one of the most fun things about putting this book together was that I got to do it with my Grandson, Reed Davidson! Reed is a Junior in High School and a really great kid! At his church he is discipling a group of junior high boys.

Second, I want to express my thanks to you and your dad for giving me your kind permission to excerpt chapter 9, “Did You Hear What Happened to Saul” from your best-selling book, More Than a Carpenter. Somehow, knowing the story of the person asking the questions gives more meaning to their questions. Understanding how Saul—a man who was involved in plots to kill those who had placed their faith in Christ—later placed his faith in Christ, gives greater depth to his questions!

Third, 262 Questions Paul the Apostle Asked is available as a free eBook @

Sean: What advice would you give to help people become better question askers?

Bob: Pre-kindergarten kids ask something like 300 questions a day. Little Johnny starts school asking tons of questions. His teachers keep sharing with Johnny that it is their job to ask questions, it is his job to answer the questions. And by the time Johnny—now called John—graduates from college, he will only be asking about 20 questions a day! We have an educational system that highly values answers—but gives almost no value to questions.

A few years after college, John becomes a leader and thinks that as a leader he needs to have all the answers. What an incredibly heavy burden for any leader to carry. When he is asked a question for which he doesn’t have the answer, he is tempted to make one up on the spot and sometimes does!

Now, here is the good news! Leadership is not as much about knowing the right answers as it is about asking the right questions!

A leader who leads with questions will often be up to 10 times more effective than a leader who only leads by telling!

Now, here is the great news! Some of the best questions are so simple. Two of my favorite questions are printed on the back of my business card:

"What do you think?"

"Can you please tell me more?"

When a leader asks his/her staff “What do you think about ________?” and “Can you please tell me more,” he/she will often hear better ideas than any they have thought of. And when they empower their staff to execute on their ideas the results are almost always superior!

The leadership guru, Dr. Peter Drucker said, “The leader of the past may have been a person who knew how to tell, but certainly the leader of the future will be a person who knows how to ask.”

Today when I am asked a question I don’t know the answer to, here is how I respond:

“Wow—that is a great question! How would you answer it?”

If they respond with, “I don’t have an answer either, that is why I am asking you,” I then ask, “Who might know or where could we go to find the answer?” They almost always have some ideas of how we can find the answer!

I then follow with, “Could you please follow through to get that answer? And then come back to share it with me?”

And I am continually motivated to ask more questions because of the model of Jesus—who knew that if you wanted to see change in someone, asking them a question would greatly increase the probability, because they would own their answer!

Of course, I invite everyone to subscribe to my blog: Subscribing is free! When they do, they will be joining leaders from more than 190 countries who are committed to growing their leadership effectiveness by moving from “Leading by Telling” to “Leading with Questions.”

Sean McDowell, Ph.D. is a professor of Christian Apologetics at Biola University, a best-selling author, popular speaker, and part-time high school teacher. Follow him on Twitter: @sean_mcdowell, TikTok, Instagram, and his blog: