The best time to graduate your succulent to a larger pot is when you see new growth on the plant. This isn't something you'll have to do often, maybe once every year or two.
Choosing a pot that is the right size for your succulent is key. As a general rule, you'll want to leave about 1/2″ (about 13 mm) between your plant and the pot. Too little room, and your plant will become root-bound. Too much room, and your succulent roots will take off but the plant itself may not grow as quickly.
Once you have a new pot picked out then follow the directions in this post!