Good teachers ask good questions. Why? Because they have been humbled by this simple point:
People learn more from what they say than from what they hear. ~ Josh Hunt
Think about it. If I can lead you in a series of questions that end with you talking about the truth I'm teaching, most often this truth will stick. Jesus knew this. That's one reason why he asked so many questions. He knew that if his listeners voiced the truth with their own lips instead of him telling them, their minds would be affected and they would remember.
Here's a few familiar examples:
"Who do people say that I am?" - Mark 8:27
"Which of these three, do you think, proved to be a neighbor of the man who fell among the robbers?" - Luke 10:36
"When I sent you out with no moneybag or knapsack or sandals, did you lack anything?" - Luke 22:35
These examples show how Jesus used questions to draw out from his listeners the correct answer he sought. Robert Stein, in his book, The Message and Methods of Jesus' Teachings, says, "By drawing out the correct answer from his listeners rather than simply declaring it, Jesus impressed the point more convincingly upon their minds."
In other words, Jesus asked good questions to make his teaching stick. So should we.