You are required to issue a Form 1099 to each person that earned over $600 in a given year. These should be mailed by Jan. 31. However, there are exceptions to who should be issued a 1099. You also must send a special version to the IRS by Jan. 31. Here’s a tip: When you pay new people for the first time, have them fill out a W-9 that requests their address and Social Security number. This will make your annual filing requirement much easier.