Monty was terribly nervous to clip the year before last - so I didn't hve him done, even tiny dog clippers sent him rearing and trying to squash people aginst the wall...
But he got sooooo sweaty, despite being rugged, being a woolly native, even his summer coat is quite thick so it was impossible to work him with a winter coat.
I ended up buying my own clippers, fortunately got them in a sale, and I spent ages choosing the quietest ones I could get hold of. I then spent six hours one day doing a three inch wide strip under his belly and up the underside of his neck - that was his first clip!
I chose a day when the yard was nice and quiet, gave him a haynet to munch, and literally took all day about it, reassuring him as I went.
His second clip that year we went a bit higher, a very small chaser, and finally in January I did a medium chase, and also clipped under his jaw (not quite a half head, more like a third!) He was perfect!
It was a combination of factors, one I'd had him a whole extra year by then (so three years last winter) and he therefore trusted me more, two I had really quiet clippers, and three I was really really patient and didn't rush him. He was only just six last year and had never been clipped, it was bound to be scary for him, but time and patience won in the end.
I'm not anticipating any major problems this year, but I will take it slowly and start off with a smaller clip just to make sure he is still confident.