Teachers need to know their students, addressing them according to their abilities. Many do this by finding a way to work as a catalyst, helping their students draw conclusions for themselves. A student who believes they have accomplished something will more likely retain what they learned than if they were just given a lecture and told to remember what they were told. This is not to say there should not be any lectures; they have their uses, but we must always keep in mind how limited they are. What is important is that a teacher should know their students, and knows how their students think; that way, they can engage their students in a way which best suits their needs.
Teachers will likely address various groups of students, and will need to do so differently for each of them. Every group, each student, has a different level of knowledge and understanding, and what that understanding is should serve as the foundation for a teacher’s engagement with them. This is why we must be careful when we are given collections of saying by famous philosophers or teachers; such collections often given the words said without context, and without that context, it might appear that there are various contradictions in what was said or written down. However, if we understood the context in which those words were said, we would better understand the meaning of the words, and so see how and why they are not self-contradictory but serve as different ways to express one and the same point. For example, if a teacher were asked where Indiana was in relation to the state they are in, the response will be different if they are in Ohio than if they are in Illinois. If that teacher had lived in both states, and had been asked that question in each of them, their response, written down without context, would be “West of us” and “East of us.” While the teacher would be correct in both situations, without context, it could seem as if his or her answers contradicted each other, indicating that the teacher was hedging his or her bets as they didn’t really know the answer.
A teacher needs to be skillful when engaging their students, using the appropriate means, the best words, symbols, and facts they can, to direct their help their student learn what they need to learn. “A teacher who is full of wisdom stammers along with his stammering young students. But the teacher’s stammering does not come from a lack of learning; it is a sign of the concern he feels toward the children.” To do this, a good teacher will often take on characteristics and qualities of those he or she is teaching, becoming like them, as a way of engagement, or, as Paul said, they can become all things to all (cf. 1 Cor. 9:22). Those who take on the youth will often take on their joys, playing with them, engaging them in a way which makes it appear they might themselves have returned to their own childhood:
Unless the one who is devoted to bringing up children regresses to childhood in every way, he never leads children to mature adulthood. For this reason at such a moment, he softens his voices, he emphasizes his words, he nods and gestures, he suspects his judgment, he changes his diet, he reduces his strength, he neglects to exercise, he slows his pace, he strives not to walk but to crawl; he pretends to laugh, he feigns fear, he sheds false tears, because in his case to lie shows his dedication, to have acted foolishly indicates his prudence, and his weakness in his strength. 
Understanding how good teachers engage their students, addressing them with the means they believe will most effectively make their points, should help us appreciate the way Jesus taught during his own earthly ministry. He came as a teacher, and as a good teacher, he addressed his audience by engaging them on their own level, using their own thought processes to serve as the foundation for what he wanted to reveal. Sometimes, to be sure, he would simply preach, but often his best lessons were given when someone directly engaged him, either by challenging him and his wisdom, or asking him for help in their lives. Such encounters allowed him to address his audience, engaging them on a personal level, indeed, it allowed him to put himself on their level so that he could then raise them up, just as he accommodated humanity (and the whole of creation) by way of the incarnation:
If he were not willing and ready to accommodate himself, it would be useless to teach sublime doctrines to those who would not listen or turn their attention to them. As it is, even if it were of no benefit to them, yet it did instruct us, it did prepare us to have a suitable conception of him, and it did persuade us that he changed to a more lowly mode of discourse because these people could not yet accept the lofty and sublime things he was saying. Therefore, when you see that he is saying lowly and humble things, do not think this is a mark of any meanness in his essence. See it is an accommodation and condescension on his part because the understanding of his hearers was weak.
And, as St. Cyril of Jerusalem pointed out, Jesus continues to address people by being accommodating to them and their needs, which is why he can be said to address the world in many different forms:
The Savior comes in various forms to each man for his profit. For to those who lack joy, He becomes a Vine; to those who wish to enter in, He is a Door; for those who must offer prayers, He is a mediating High-Priest. Again, to those in sin He becomes a Sheep, to be sacrificed on their behalf. He becomes “all things to all men” remaining in His own nature what He is. For so remaining, and possessing the truly unchangeable dignity of the Sonship, as the best of physicians and a sympathetic teacher, He adapts Himself to our infirmities. He is Lord in truth, not having advanced to the Lordship, but possessing that dignity by nature. He is called Lord, not improperly as we are, but in the very truth He is Lord, since by the decree of the Father He has Lordship over His own works. 
Once we appreciate this, we can better engage the Gospel accounts we have which indicate some of what he taught during his temporal ministry. We will understand, in each story, in each lesson, in each engagement, his words were carefully chosen to deal with the situation at hand. Though there can be and are universal truths presented in them, often that truth is pointed to by his words instead of expressly stated by him. We can’t take his words at face value; we must look beyond the letter to find the meaning which lay be them. As a good teacher, he often asked questions, not because he did not know the answer, but because he knew by asking it, he could lead his interlocutor to a higher truth as they tried to find the correct answer to the questions for themselves, or else, he wanted the person to reveal to others what he or she had done so that the grace which was imparted in the situation could be known by all. Thus, when he asked the rich man why he called him good, Jesus was not denying his own goodness, but rather, he questioned the reason why the rich man called him good and he wanted the man know he was not accepting flattery (cf Mk. 10:17-18). Similarly, when a woman suffering a continuous flow of blood touched him, he asked who touched him, not because he didn’t know, but because he wanted her to reveal herself to everyone so that everyone can see her for her great faith (cf. Lk. 8:43-48). We can also see this in the way he engaged a Canaanite woman– he did not want to deny her grace, as he had come to save the whole world, but he wanted her to make the case for his ministry to be of universal value, that is, through her, he wanted to reveal that everyone could be seen as included in his ministry (cf. Matt. 15:21-28). This is also why Jesus spoke in parables, for he knew parables were able to teach people to think for themselves, to reflect upon what was taught, so that once they discerned the truth, they would feel they have accomplished something and would want to put the truth they learned into effect.
Teaching requires many skills. A great teacher must have wisdom and knowledge which is worthy to impart. They must also understand what their students know and use that as the starting point of their teaching. Because of this, when we find Jesus teaching someone, we should understand the context in which his words are found. If we do not do so, we can easily confuse the simple letter of the text as being the intended meaning and totally misunderstand Jesus’s point in using particular words and phrases. Thus, there are some, after reading the Gospels, who think Jesus was denying his own inherent, or that he seriously thought his work was to be done exclusively for the Jews. The point of his words, however, was not to conclude such, but rather, the opposite; he wanted the rich man to know he was good because he was God, even as he wanted the Canaanite woman to have her wishes fulfilled and bring spiritual healing to her and her family. Those who misread his words, especially if they overly literalize them without understanding the meaning intended by them, not only cause confusion, they end up suggesting Jesus constantly contradicted himself. Jesus didn’t. He was a good teacher. He knew words alone were not enough to impart truth. He knew they should be used as pointers so as they can lead his audience to greater and greater truths. And thus, when we engage him, when we engage what he said, we should do what we can to understand his intended meaning instead of engaging the letter of what he said and think that is all we need to know.
 St. John Chrysostom, On the Incomprehensible Nature of God, 196 [Homily 7].
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