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Asking the Right Questions

Updated: Mar 25, 2021

Did you ever wonder why Jesus asked questions all the time? Well, that was a common practice of the ancient rabbis. Educators of our own day know that people learn through a process known as critical reflection – a process of pondering and thinking about things so as to understand something. This is specifically true for adults – we learn through our own reflection, figuring the meaning of something out for ourselves. Andragogy is a term used for learning by adults, where pedagogy relates to the education of children, with the latter meaning “to lead the child.”

When Jesus entered into a dialogue with someone, He would ask questions to help other people think reflectively on what He was saying, helping them to come to the understanding of what His teaching meant. Dialogue – and questions – played a big part in how the rabbis taught. Here is an excerpt from my book The Way of the Master: The Leader Methodology of Jesus, which elaborates a bit more deeply on His use of questions:

One of the core elements of Jesus’ verbal exposition was the use of dialogical methodology. An excellent example of this was Jesus’ dialog with the woman of Samaria at Jacobs well (ref. John 4:1-25). Here, Jesus uses the setting of the encounter – Jacob’s well – as the crux of the metaphor at the heart of the discussion in a truly integrated teaching moment. Life is the curriculum, there is an andragogic discovery learning process based on dialog, and as always, there were questions.

Critical reflection is a fundamental element to the rabbinic process, and the use of questions plays a key role. Jesus was famous for His questions. Steven Silbiger pointed out how the rabbinical process of question asking has come down to the current era: “The Jewish religion focuses on the individual and his or her own spiritual life and journey. It is therefore important that Jews are involved in spirited discussion and debate about the various stories and laws in their religious texts as a means of forming a personal and intellectual attachment to their religion (Silbiger, 2009, p. 24).

He contrasts this with contemporary Christian religious education and its dogma which is to be accepted by faith – with little or no dialog or questions asked. Noting this departure from the rabbinical process, he goes on to point out how the inclusion of dialog in education plays out in the critical thinking skills of Jews:

Beyond the context of religious readings, critical thinking skills are encouraged and developed in the Jewish community. These highly transferable skills also form the basis for many secular pursuits in the humanities, the sciences and business. It is therefore not surprising that 40 percent of American Nobel Prizes in science and economics have been awarded to Jews, and Jews have won 25 Percent of all Nobel Prizes awarded to Americans. Despite a lack of secular educational opportunities throughout their history, the Jews’ religious training created a literate and intellectual culture that celebrated academic achievement (Silbiger, 2009, p. 25).

A very poignant example of Jesus use of questions as part of His illuminating methodology is found in His discourse with His disciples in Matthew 16:13-20. He asks an initial observational question (“Who do people say that the Son of Man is?”). This is followed by an affective/interpretive question, making the dialog much more personal (“But who do you say that I am?”). Here he draws out His learners, helping them differentiate from the thinking of the crowd, and therefore come to the discovery of who they think He is. In the shaping of His cadre of proto-leaders, Jesus does more than just communicate a core body of knowledge; He uses questions as His main methodology in even His most basic instructional settings. Such questioning is essential to the development of the leader, as Logan and Miller note:

Because each new leader is a unique person asking questions, each one needs a guide. Someone to come alongside them as they learn, providing direction, encouragement, and feedback. Someone to act as a sounding board for their questions and help them process their options. It takes time to get people started well; they don’t learn everything all at once. No initial orientation can cover everything that needs to be covered. So it shouldn’t try (Logan & Miller, 2007, p. 37).

As Whitworth noted “Powerful questions invite introspection, present additional solutions, and lead to greater creativity and insight” (Whitworth, Kimsey-House, & Sandahl, 1998, p. 69). It is this insight derived from the critical reflective process facilitated by the rabbi’s questioning. It is the integrated understanding of Torah the rabbi is looking for, and questions are the discovery methodology. Whitworth, when speaking of the professional development of leaders, so eloquently stated: “Think of questions as caves and tunnels. Asking a powerful question is like sending the client into a vast and intricate tunnel system that leads to other tunnels, discoveries, and mysteries” (Whitworth, Kimsey-House, & Sandahl, 1998, p. 69). It is this “tunneling” back behind the superficial aspect of some aspect of life that Rabbi Jesus is seeking to do, engaging His learners at a deeper level.

Another example of His use of questions is in His response to a question asked about paying taxes. Seeking to engage Jesus in a classic rabbinic debate on the observance of the Law, the Pharisees and Herodians try to trick Him by bringing into the debate Roman occupation of Palestine. They want to see if He will support the Romans and, in their view, violate the Torah or if He will speak openly against the Romans:

Then the Pharisees went and plotted how to entangle him in his words. And they sent their disciples to him, along with the Herodians, saying, “Teacher, we know that you are true and teach the way of God truthfully, and you do not care about anyone’s opinion, for you are not swayed by appearances. Tell us, then, what you think. Is it lawful to pay taxes to Caesar, or not?” But Jesus, aware of their malice, said, “Why put me to the test, you hypocrites? Show me the coin for the tax.” And they brought him a denarius. And Jesus said to them, “Whose likeness and inscription is this?” They said, “Caesar’s.” Then he said to them, “Therefore render to Caesar the things that are Caesar’s, and to God the things that are God’s.” When they heard it, they marveled. And they left him and went away (Matthew 22:15–22).

They begin with flattery, but Jesus calls out their hypocrisy. He then answers their question with another question (observational/perceptive) to make His point: God is not concerned about the Kingdom of the Romans and their taxes, what He wants is what should be in His Kingdom – an offering of the whole life. Through questions, Jesus often sought to reveal the hearts of people as to which kingdom their allegiance belonged.

As Kreeft noted, the ability to reflect through questioning is a uniquely human ability, and differentiates us from other living things:

But there is one simple, observable behavior that clearly distinguishes humans from both computers and animals: asking questions. Computers never question their programming (unless they have been programmed to do so); computers never disobey. They have no will, therefore no will to know. And animals, though curious, cannot ask formulated questions; their language is too primitive. There is a story that Aristotle, after one of his lectures, was disappointed that his students had no questions afterwards, so he said, “My lecture was about levels of intelligence in the universe, and I distinguished three such levels; gods, men, and brutes. Men are distinguished from both gods and brutes by questioning, for the gods know too much to ask questions and the brutes know too little. So if you have no questions, shall I congratulate you for having risen to the level of the gods, or insult you for having sunk to the level of the brutes?” (Kreeft, 2010, p. 35)

From this except we can Jesus using questions to help people see the Kingdom by confronting their behaviors, processing their own beliefs, and coming to their own realization of what the Lord was teaching. Such questions confounded His adversaries, exposed the hearts of people with whom He spoke, and brought revelation to those with open hearts.

In the church which I have the privilege of pastoring, you might find quite a few people who will have a humorous story about my own use of questions – and some who may roll their eyes and chuckle when you ask. I frequently answer a question with a question, often causing momentary frustration with the person who asked, yet leading them towards a deeper discovery process of their own. I encourage people to understand, not just know. Question are powerful tools which can help people come to their own understanding of the Jesus way, one which they “own” and internalize, making it part of their life. Questions are a key element in the way of the Master, Jesus.

More on how Jesus used questions in our next installment!

Excepted and edited from The Way of the Master: The Leader Methodology of Jesus, Pgs. 75-77 now available for Kindle on

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