Jesus knew who He was speaking to and used examples that were at His audience’s level. With the crowds He spoke parables using examples that they saw everyday. Yeast in flour, marriage feasts, and sowing crops are examples of things He used in parables to illustrate the Kingdom of God. His parables could be taken on multiple levels of understanding but I think the meanings were always hidden because Jesus wanted people to ask questions. Isaiah had talked about this fact when he said that they would be “ever hearing but never understanding”; just because you enjoy a story does not mean that you understand the symbolisms and metaphors that are written into it by the author. With the leaders His meanings were still veiled but they knew when he was talking about them; the example here is the Good Shepherd vs. the hired help.
He used current events as part of His teaching like when he talked about the tower that fell or when Pilate mixed pigs blood into the sacrifice.
Jesus used various strategies for where He was and whom He wanted to reach. He talked to massive crowds, small groups, and even one-on-one when the people or persons needed that in order for His message of the Kingdom to be gotten out and understood. He would launch a discussion question like, “Who do the people say I am” or He would ask a question and patiently wait for an answer like when the woman was about to be stoned for adultery. (Of course that could be Him as a Master Judge also.)
Since He had chosen the disciples they got special treatment. He would explain parables to them but He knew that He would have to send the Holy Spirit (re-teach) because they were not progressing fast enough. They got quantity and quality time with Jesus and I think He even gave them tests. If I may, the teaching that God can provide was the feeding of the five thousand and their test was the feeding of the four thousand. (see Test Revisited)
The picture was taken at Houston Baptist University.