Socrates assumes a number of guises. He partakes of the Greek ideals of rational discourse and intellectual "combat", but "rationalism" is not his teaching, as the moderns think. His "teaching", in fact, is rather odd. He seems to have no teaching at all and appears only to engage in enquiry. Aristotle notes, "Socrates used to ask questions and not answer them, for he used to confess that he did not know". At the same time Socrates refused to be called a master of wisdom. Epictetus says of him, "When people used to come and see him, they asked him to introduce them to lovers of wisdom; he readily complied, and at the same time willingly accepted to pass unnoticed himself." Pierre Hadot writes, "Since he had nothing to say, and no thesis to defend, all Socrates could do is ask questions, even though he himself refused to answer them." One is reminded here of Nagarjuna's paradoxical utterance in his Vigrahavyavatani: "I have no thesis (pratijna) to defend".
When we look at the "Socratic" Dialogues with this interpretive key, and consider them as literary works, we can see that "Socrates" is not so much interested in teaching a "theory of ideas", or what the "real" definition of justice is. He is actually only interested in his interlocutors. In the Apology he confesses that it has, all along, only ever been about teaching what each of his interlocutors "is". In the Dialogues, the enquiry winds about, comes to an impasse, Socrates takes it over, and then it all comes to a puzzling end, at which point both we and the interlocutor are not clear as to what it is we have learnt. But the pattern is always this: Socrates questions someone who thinks they know what they are talking about, and by the end of the interrogation it becomes quite clear that they don't know what they are talking about. The "teaching" here is simply that one should understand the limits of his knowledge and the limitations of his noetic capacities.
This same Socratic theme of knowing one's limitations reappears in the works of Kierkegaard, and here we find the other dominant "figure" in the West: that of Jesus. Here, the issue becomes not so much whether or not Kierkegaard's contemporaries are sages, but the degree to which they can be called "Christians". Kierkegaard sets an almost impossible standard here; indeed in his version of the "imitation of Christ" the only true Christian can be Christ himself. Just as Socrates finds no true sages among his peers, Kierkegaard finds no true "Christians".
We might say that for the ancients, the image of the "sage" functions entirely as a kind of "transcendent norm". Sage-hood lies beyond the grasp of the mere mortal, but it is something that should be striven after nonetheless. While sage-hood functions as a kind of transcendent norm that can only ever be approached asymptotically, the practical paradigm becomes that of the lover of wisdom, represented by the figure of Socrates (and other figures such as Pyrrho, Diogenes, Epicurus, and so on). Two of the characteristic features of this general teaching of the ancients can be said to be the teaching that the lover of wisdom is a composite of both wisdom/knowledge and folly/ignorance, and that the lover of wisdom unceasingly engages in enquiry (zetesis; skepsis).
According to Nietzsche, there are two sides to Socrates the teacher. One is the seducer of youths who rips the masks from the gods, dissolves their myths, and replaces them with the "knowledge of good and evil". As Hadot points out, this is the Socrates that Nietzsche despises, because this was what Nietzsche himself was so good at. The other is Socrates as the "midwife" of the soul, the Socrates who teaches his students to "care for their self". This is the Socrates that Nietzsche admires and envies, because he found this capacity to be so lacking in himself.
Hadot points out that the teacher as "midwife" does not so much engender the soul of the student as allow the student to engender his own soul. Somewhat paradoxically, the teacher teaches by becoming a kind of student himself. Kierkegaard writes, "The student is an opportunity for the teacher to understand himself, just as the teacher is an opportunity for the student to understand himself." Here, teaching, paedeia, becomes a kind of "spiritual exercise" in itself, and its paradigm of the teacher who remains the perennial student becomes an expression of the ideal of unceasing enquiry.