Preparing 1099s at year-end goes much smoother when you already have a running total per contractor, plus their W-9 information on file, rather than reconstructing everything from invoices in January. This template tracks both throughout the year.
Included in the $7/mo Tools Club · Works in Excel or Google Sheets · Includes a built-in AI prompt
January is already a busy month for year-end close and tax prep — adding "reconstruct a year of contractor payments from scratch" on top makes it worse. Keeping this updated throughout the year means 1099 season starts with the data already assembled.
Download and open in Excel or Google Sheets
Requires a Tools Club membership — log in first to access the file.
Set up a row per contractor with W-9 status
Collect the W-9 before or with the first payment, not scrambled for in January.
Log every payment throughout the year
Real-time entry keeps the running total accurate.
Review the automatic threshold flag as the year progresses
This shows you which contractors are approaching or have crossed the current reporting threshold.
Run the built-in AI prompt as year-end approaches
Attach the saved file to ChatGPT or Claude and ask if your records look complete for 1099 preparation.
Built-in AI prompt
Once you've filled this template in, it includes a ready-to-use prompt at the bottom of the sheet. Attach your saved file to ChatGPT, Claude, or any AI chat tool and paste it in — you'll get plain-English feedback on whether your contractor payment records look complete and ready for 1099 preparation, and what’s commonly missing at this stage, no accounting background required.
Not collecting a W-9 before the first payment
Chasing down a missing W-9 in January, right when you need to file, is a common and avoidable scramble.
Missing payments made outside your normal invoicing process
A reimbursement or one-off cash/check payment can be easy to forget — log every payment, not just regular invoices.
Assuming the reporting threshold hasn’t changed
Thresholds and specific reporting rules can change — verify the current requirement rather than assuming a fixed number indefinitely.
Not distinguishing contractors from vendors selling only goods
Reporting requirements often differ between payments for services versus simple product purchases — check current rules on what specifically needs to be reported.
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