When I have to medicate my dogs, I put the pill in a blob of peanut butter on my finger (they've already learned to like it with Kong toys, etc). They swallow it down before they ever realize there's a pill in there. With the head shaking after medication, at least in my cats (ear mites, yuck!), it seemed to help if I massaged the base of their ear to work it on down inside, but sometimes they still beat me to it with a head shake, and yes, medicine all over.

Good luck!