I think the easiest way, once you have rolled out the dough, is to take one side and roll it onto the rolling pin (Use a bench scraper to release it from your countertop if the dough has gotten warm and is sticking). You should be able to roll about half the crust onto the pin. Now just slide the pan underneath the rolling pin/crust and unroll the crust from the pin. You might have to do some adjusting to make sure it is even in the pie pan.