January-you will thank December-you.
One sitting in December: list your contractors, collect the missing W-9s, count who crossed $600. Then January is a handoff, not a scramble.
What's inside
Two files. Records only — your CPA makes the calls.
Vendor tracker
Forty rows with dropdowns for entity type and W-9 status. W-9 missing turns red; totals at $600 or more turn amber. You can see your whole list's status at a glance.
Triage tab
Counts it for you: vendors tracked, who you paid $600 or more, and how many of those still have no W-9. That last number is your December to-do list.
CPA handoff checklist
The seven things your tax preparer typically asks for in January — tracker, W-9s, payroll reports, YTD P&L, December statements. Check them off as you collect.
One-page paper version
The rule of thumb, your five-minute December list, and room for a pen. Pin it above the desk until January.
The rule of thumb
Plain English — and your CPA always makes the final call.
Who typically needs a 1099-NEC from you
Honesty first: this is record keeping, not tax work. This workbook doesn't decide who gets a form and doesn't file anything — your CPA does that. What it does: makes sure the records are ready when they ask, so their January is cheap and your bill is small.
Questions, plainly answered
The ones people actually ask.
Does this file my 1099s?
No — deliberately. Filing is tax work, and that belongs to your CPA or tax preparer. This kit gets every record they need into one tidy place, with a handoff checklist so nothing gets asked twice.
What about my W-2 employees?
Employees are payroll, not contractors — the handoff checklist includes your payroll reports for the year so those go to your CPA complete too.
It's October. Am I too early?
You're exactly on time. W-9 requests go out while people are still answering email; waiting until January turns a two-minute ask into a chase. Future-you approves.
Pairs well with
The rest of the shelf, if you want it.
Books Health Check
Question 8 on the scorecard is literally this. See how your whole books score in three minutes.
Small Biz Books Starter Kit
If the vendor list is the easy part and the books behind it are the mess, the Kit is the cleanup system.