I don’t really know much of anything about Zen, but to me, one of its main concepts is essentially that whenever we think about something, we don’t really think about things, in the sense that there are no actual things present in our thoughts, but about names of things; i.e. if I think about a tree, there’s no actual tree present in my mind (thankfully, because I’d imagine that could hurt a little), but merely the concept, the idea, the image or ‘name’ my mind uses to represent a tree. All our thoughts are ever concerned with, then, are such names or representations; they never touch the actual ‘thing itself’. If we think of names – or more general, the words or whatever other elements may comprise our thoughts – as entities present in the world, that means that our mind only ever touches a vanishingly small part of the world (namely, those names, words or whatever you wish to call them).
Zen then consists at least in part in the realisation that our thoughts and the things they represent/name may well be dissimilar – hence, ‘the Tao that can be named is not the true Tao’. This has some consequences for the concepts of meaning and understanding: Generally, a word (or thought) means something if it stands in some correspondence with some concept; i.e. the word ‘tree’ means the thing tree since there is some sort of mapping from one to the other. Understanding similarly means the capacity to in some sense represent some process within the mind. However, if we recognize the difference between thoughts and things, then there is no real reason that there must exist a one-to-one mapping between the two; there might be things that are unthinkable, at least as long as thinking is restricted to the words-and-concepts mode.
Koans are designed to break this ordinary discursive mode of thought; as such, there is no real, true understanding of a koan, and it does not have a meaning in the traditional sense; rather, they are perhaps best viewed as exercises for the mind. They are necessary, for of course it would be futile to try and teach Zen straightforwardly, using words and concepts: the very idea of doing so is self-contradictory. Rather, you’re supposed ‘get used to’ a non-discursive, Zen way of thinking through the practice of koans. Perhaps an analogy is thinking in pictures: it’s hard to describe a picture exactly in words, but seeing the picture gets the information into your mind instantly. Of course, pictures are really just more general names…
In this way, there is no real metric to grade your Zen-examination: whatever will be written won’t be Zen anyway, whether it comes from a master or not; there’s no right or wrong answer to/interpretation of a koan – there’s not really an answer or interpretation at all, I think. I’m not sure there’s any good way to prove enlightenment to another, or discover another’s enlightenment, even: those are discursive concepts, and need not necessarily apply.
That said, there’s probably some sort of ‘talk of the trade’ by which you could distinguish the Zen-ness of the responses from one another; however, the Zen-ness thus distinguished won’t be the true Zen-ness.
Of course, I might just be babbling; this is really only my take on the matter, formed by rather casual exposure to Zen matters.