The foundation is collecting a W-9 from every subcontractor before you pay them. The W-9 gives you their legal name, address, and tax identification number, which you need to file the 1099. If you wait until January to chase down W-9s, you’ll spend weeks tracking people down, and some won’t respond at all. Get the W-9 before you cut the first check.

Through the year, track total payments per subcontractor. You need to know exactly how much you paid each person by December 31. If you’re using QuickBooks Online, set up each sub as a vendor and pay them through the system so the totals are already there when you need them. If you’re paying people by check or Zelle without recording it properly, you’ll be reconstructing from bank statements at year end. Good bookkeeping and tax services will keep these totals organized for you automatically.

For payments made in 2026, the federal filing threshold for 1099-NEC rose to $2,000, up from the $600 threshold that applied for years. Anyone you pay $2,000 or more for services during the year needs a 1099-NEC. The thing is, you don’t know in January whether you’ll hit $2,000 with someone by December. Collect the W-9 from everyone anyway. It costs you nothing to have it, and scrambling in January for a W-9 you didn’t collect costs you time and stress.

If you’re in Massachusetts, keep in mind the state has its own reporting threshold that’s lower than the federal. State filing can be required even when federal is not. This catches business owners by surprise when they think they’re clear federally but still owe a Massachusetts filing.

1099 preparation is something we handle for service businesses across New England and nationwide. We track who needs a 1099, gather the details, and file the forms by the deadline. If you’d rather hand off the year-end scramble to someone else, reach out for a consultation about your situation.