You need to send him a W-9 to find out. If it is filled out that he is an individual sole proprietor/contractor, then yes, you need to issue a 1099NEC to him for his paid services. If it is returned to you with either S-Corp or C-Corp checked, then you do not need to issue a 1099. Remember to check with your state DOR to find out their requirements for 1099 filings as well.
