New Tew
I am also fairly new to squirrel hunting. Especially with a dog. I have two black mouth cur pups, one of which I would like to train to tree. I think one of the first things you can do is get a squirrel tail and see how interested the dog is in the scent. I am sure he will be interested. I let my pups play with the squirrel tail a little.
Then I have started laying trails with the scent of live squirrels or hides. You can hang a live squirrel or hide in a tree. See how he reacts. I am new so this is also trial and error! I have heard you don't want to show them too many hides and live squirrels put up in trees or they will slick tree, treeing where there is no squirrel.
I would say get them interested enough in the one type of game and then just go from there. Set up a few man made situations and then see where it goes from there. Get out in the woods a lot.
Also, check out the chat room at sqdog.com.