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Collect W-9s from vendors before 1099 season with AI

Find the contractors and vendors you may owe a 1099 and send them a polite W-9 request in December instead of chasing them in late January.

Estimated time saved

Estimated: several hours of January chasing, plus fewer late or wrong 1099s. (Estimate; results vary.)

Tools
  • ChatGPT
  • Claude
  • Your accounting software (QuickBooks, Xero, Wave)
  • Google Sheets or Excel
  • IRS Form W-9 from IRS.gov

The problem

Small businesses have to send 1099-NEC forms to many independent contractors by January 31. The scramble usually starts in January, when owners discover missing W-9s, wrong addresses and vendors who don't answer.

Step by step

  1. 1Run a vendor payment report for the year from QuickBooks, Xero or Wave and export it to Google Sheets or Excel.
  2. 2Mark which vendors are individuals or LLCs you paid for services and which already have a W-9 on file. Check the current 1099 reporting threshold and rules on IRS.gov or with your accountant; they changed for 2026 payments.
  3. 3Paste the prompt below (vendor types only, no tax ID numbers) to get a short W-9 request email, a follow-up and a tracking sheet layout.
  4. 4Send the request with a link to the blank W-9 from IRS.gov and ask vendors to return it through a secure method, not plain email, since it contains a tax ID.
  5. 5Track who has replied, follow up in two weeks, and hand the finished list to your accountant or 1099 filing service.

Copy-paste prompt

Prompt
I run a [type of business] and pay about [number] contractors and vendors a year. I need W-9s from the ones who don't have one on file before 1099 season. Write: (1) a short, friendly email asking a vendor to send a completed W-9 by [date], with a link placeholder [W-9 LINK] and a note to send it through [secure upload / fax / mail] rather than plain email; (2) a polite follow-up for vendors who don't answer in two weeks; (3) a tracking table with columns Vendor, Type of work, Paid this year, W-9 on file (Y/N), Requested date, Received date, Notes; (4) a short list of questions to ask my accountant about which vendors need a 1099. Don't state IRS thresholds or deadlines as fact; mark anything I should verify with [VERIFY].

Review AI output before using it. Don’t paste confidential, customer or patient data into tools your company hasn’t approved.

Free · 5 minutes

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