Thanks for all the help guys! Perhaps I should explain the pole issue further and what I tried last night, just to clarify. He is not a high energy horse, he is not spooky, he is young and not very confident. He is very sensitive and holds on to bad experiences and its NOT (just) me - I have have evidence but please just trust me otherwise this will be a long post!*if you want another good example I can give it in another post.
So last night a horsey friend came up, I didnt tell her about the pole thing. She put the pole on the ground and then went to lunge him over it. He stopped, put his head up and blowed a couple of times. She tried to encourage him forward he danced around a bit with his feet and swung his butt away from her and blowed again. She tried to keep moving him forward and he just tried to either change directions or come towards her. This is exactly what he does for me. So then I do as suggested the advance retreat (and sometimes you don't even have to do that) then he'll go over. It seems he needs to see a person or a horse go over it, then he will tentatively go over it. After that he will go over it, but if given the choice he would go around it everytime instead of over them. Anyways the point is that while I know he is learning he can stop which isn't good, this is a fear based behaviour so how to I go about convincing him he can do it on his own without intensifying his fear? (this is why I mention he's sensitive, you push him too forcefully and he wants to flight until you take the pressure off)