How to Ask Good Questions


Question: How can we provide answers that our disciples can fully grasp?

Answer: With questions.

So, how do you ask great questions?

Let’s see what the ancient rabbis have to teach us about this.

Sh’eilah is the Hebrew word for question, and sh’eilot is Hebrew for a series of questions asked of one expected to have answers. Notably, The Jewish New Testament Commentary points out that this ‘putting of sh’eilot,’ or asking questions, was not one-sided. Instead it led to a dialogue, as in Jesus’s conversation with the teachers in the temple at age twelve. ¹ Some Bible scholars estimate that Jesus was asked 300 questions during His ministry, but He gave a straight answer to only three. They also say that Jesus Himself asked around 125 questions, many of which were in answer to questions He was first asked. In other words, if you asked Jesus a question, you had better than a one-in-three chance of being asked one in return!

Rabbis answer by asking.

Why? For the purpose of understanding.

Many years ago, I came up with a simple but effective way of teaching this. I take a short piece of rope, about 10 inches long, and explain that one end of the rope represents a question we might ask, while the other end represents the answer we want. Almost every human being who asks a question is hoping to get from one end to the other as soon as possible. We want answers, and we want them fast.

However, when we ask a question, the question itself can reveal something vital that we do not yet understand—significantly, something more important than the actual answer!

A very simple example of this occurred when the rich, young ruler approached Jesus.

Just then a man came up to Jesus and asked, “Teacher, what good

thing must I do to get eternal life?”

“Why do you ask me about what is good?” Jesus replied. “There is only

One who is good.” ²

The first part of the question, “Why do you ask me about what is good?” may seem odd. Stranger, however, is the rest of it: “There is only One who is good.” The rich, young ruler wants to know what he can do to enter heaven. Jesus’s first question reveals something more important that the young man needs to understand. By asking the question to point out that only

God can do good, Jesus is hoping that the rich, young ruler will realize the true identity of Christ. The real question the man needed to ask was not:

What do I need to know?”

But rather:

Who do I need to know?”

Sadly in this case, the man does not grasp what Jesus is saying, and, therefore, Jesus simply continues to answer the questions presented to Him.

When someone asks me a question that reveals something more important that they do not understand yet, I put a knot in the rope. The knot represents a mystery that they have not yet grasped. Helping them first understand this principle or pattern becomes my primary goal. Sometimes I create the knot in my mind and sometimes physically in front of them, depending on the situation. Then I follow the rabbinic process, which is to keep asking questions until the person understands that primary mystery:

When the spirit saw Jesus, it immediately threw the boy into a convul-

sion. He fell to the ground and rolled around, foaming at the mouth.

Jesus asked the boy’s father, “How long has he been like this?

“From childhood,” he answered. “It has often thrown him into fire or

water to kill him. But if you can do anything, take pity on us and help us.”

“‘If you can?’” said Jesus. “Everything is possible for one who believes.”

Immediately the boy’s father exclaimed, “I do believe; help me over-come my unbelief!” ³

The man thought that the answer to his distress lay in Jesus’s ability to heal, but through two questions he came to understand his answer lay in his own ability to believe. Once he grasped this, the answer was obvious to him. He no longer asked for a miracle for his son, but a miracle for himself. Note that Jesus did not tell the father that this was the key; He led him to that  understanding through questions. In the same way, once my disciple understands the mystery, I can unravel the knot and they will often be able to answer their question for themselves.

In fact, once the principle is understood, the answer tends to come immediately afterwards.

** This excerpt is taken and adapted from author Paul Clayton Gibbs’ book Talmidim: How to Disciple Anyone in Anything. Learn more about how to ask good questions and discipling others by getting your own copy of Talmidim today! **

  1. David H. Stern, Jewish New Testament Commentary (Clarksville, MD: Jewish New Testament Publications), p. 110.

  2. Matthew 19:16-17.

  3. Mark 9:20-24.