Hello boweevil. The trailing shoe is the larger of the two. When you buy new shoes for drum brakes, they come in pairs, 2 for the left side, and 2 for the right. 2 shoes will have slightly less friction material on them. These are the lead shoes, and will go toward the front of the car. The shoes with more material are the trailing shoes and will be toward the rear of the car.
On a side note, if this is your first time doing drum brakes, it is a good idea to do one side at a time so you can use the assembled side as a reference for the side you are working on. Also, there are a few precautions to take to ensure you get the most out of your new brakes so you do not have to do this again sooner than expected. First off, be sure to clean the backing plate off well. It should be dusty from brake wear. However, if it is greasy, then you most likely have a leaking wheel cylinder, and that should be replaced while you are in there. If you do replce the wheel cylinder, be sure to bleed the brakes after the brakes are reassembled. Another precaution is to cover the friction part of the shoe with masking tape before handling them. This will ensure the surfaces stay clean and grease free during assembly. I keep the tape on the shoes until I am ready to slide the drum on. Finally, check the drum for warpage, out of roundness, and check for a lip on the inside. If any of these conditions are present, find a machine shop to "turn" your drums, or replace them. This will ensure that your brakes will last as long as they should, and that that they will feel normal when being applied.
There is a good article on this site that shows pictures of drum brakes being replaced:
http://www.automedia.com/Replacing_Brake_Shoes/ccr20021101bs/1
Good luck.