Get Your Year-End Contractor Paperwork Ready Before January Sneaks Up

It happens every year. Christmas comes and goes, and then your bookkeeper or accountant asks for the list of every sub you paid, their tax info, and the totals. Half the W-9s are missing. One sub changed his business name. A pile of receipts is still riding around in the truck console.

This note is for owners of small plumbing, electrical, HVAC, roofing, and building shops who pay subcontractors or independent helpers during the year. The problem is that year-end paperwork gets left until the last minute, when the people you need to reach are busy too. The fix is spending an hour or two now, in late October, using AI to build your checklist and find the gaps. Your accountant or tax preparer still decides what gets filed, and they do the filing.

Keep private numbers out of the chatbot

Don't paste Social Security numbers, tax ID numbers, or bank details into an AI tool. You don't need them for any of this. Use names, rough totals, and yes-or-no notes like "W-9 on file." The real numbers stay in your bookkeeping software or a locked file.

Make a list of everyone you paid

Pull a list of vendors and payees from your bookkeeping software, bank statements, or check register. Then paste just the names and yearly totals with a prompt like:

"I run a small Louisiana trade business. Here is a list of people and companies I paid this year with totals. Sort it into three groups: likely subcontractors or independent workers, suppliers and parts houses, and anything you can't tell. Don't guess at tax rules. Add a column for questions I should ask my accountant."

What comes back is a starting point, not a tax answer. It helps you see who you need to talk about with your accountant.

Find the gaps while there's still time

Next, ask AI to turn that list into a simple checklist for each sub:

• W-9 on file? If not, send a request now, not in January.
• Name and address current? Subs change business names, move, or form a company.
• Payments matched? Check that your totals line up with your bank records.
• Any cash or card payments that never made it into the books?
• Proof of insurance or license on file, if your contracts call for it.

AI can also write a short, friendly text or email asking a sub for an updated W-9. Read it over and send it yourself.

Round up the receipts

If receipts live in a shoebox, a phone camera roll, or the truck, set aside a Saturday morning in November to gather them. AI can help you sort a list of expenses into the categories your accountant uses, so the January meeting goes faster. The IRS explains what records a business should keep and for how long on its recordkeeping page, linked below.

A small, low-risk way to start

Pick your five biggest subs from this year. Check whether you have a current W-9 for each and whether your payment totals match the bank. That's a one-hour job, and it tells you how much cleanup the rest of the list needs. If it all looks good, great. If not, you found out in October instead of January.

If you'd like help setting up a simple year-end checklist that fits the way your shop pays people, you can book a short call and we'll walk through it with you.

Sources & useful links

• IRS: About Form 1099-NEC. The official page for the form businesses use to report payments to independent contractors, with current instructions and due dates. Rules and amounts can change, so check this page and your tax preparer each year.
• IRS: Forms and associated taxes for independent contractors. Explains the forms involved when you pay independent contractors, including the W-9.
• IRS: Recordkeeping. IRS guidance on what business records to keep and how long to keep them.
• SBA: Pay taxes. The SBA's small-business guide to federal and state tax responsibilities.