W-9 and 1099 Playbook: What Broke + Simple Fixes

The W-9 and 1099 playbook usually starts the same way: it’s late January, your team is tired, and someone asks a simple question “Do we have W-9s for everyone who needs a 1099?” That’s when the calm disappears. You open the vendor list and see missing forms, duplicate vendors, and names that don’t match what’s on file. Suddenly, you’re not doing accounting work anymore. You’re doing detective work.

And here’s the annoying part: the stress isn’t caused by tax season. Tax season just exposes the gaps you already had.

This post is a clean W-9 and 1099 playbook you can use right after the deadline rush so you don’t repeat the same pain next year.

What actually broke this season (and why it keeps happening)

Let’s talk about “Nina.”

Nina runs AP. She’s sharp. She cares. She follows up.
Still, January turns into a mess.

Here’s what happened:

• A contractor started in March. Someone said, “We’ll get the W-9 later.”
• Later became “after the first payment.”
• Then it became “we’ll find it in email.”
• Meanwhile, the vendor name in the accounting system was “Mike Johnson,” but the W-9 (if it exists) says “MJ Media LLC.”
• In January, Nina is chasing forms while also trying to close the books.

Nina didn’t fail. The system failed Nina.

This is the core issue: you don’t have one trusted source of vendor truth.
Instead, you have a vendor record, a spreadsheet, an email thread, and a folder called “W9s (new new).”

That’s why this W-9 and 1099 playbook matters.

If you’re still chasing forms right now, read: “Missing W-9s in January? The Late-Filer Survival Guide (With Copy-Paste Email Templates)”

The “pain points” that show up in almost every company

1) Missing W-9s because onboarding didn’t require them

If collecting a W-9 is optional, vendors treat it like optional homework.

2) Duplicate vendor records

Duplicates create confusion, wrong totals, and name/TIN mismatches.

3) Legal name vs DBA mix-ups

Invoices often show a DBA. The IRS wants the legal name tied to the TIN.

4) W-9s stored in email (or lost in downloads)

Email is not a filing cabinet. It’s a maze.

5) No clear owner

When “everyone” owns W-9 collection, nobody drives it to completion.

The W-9 and 1099 playbook rules (simple and non-negotiable)

Rule 1: “No W-9, no vendor setup”

This is the easiest win.

You don’t even need to start with “no W-9, no pay.”
Start with: we don’t activate a vendor until the W-9 is received (or the correct form if they aren’t a U.S. vendor).

This one rule removes 70% of the January scramble.

Rule 2: Stop collecting W-9s through email

Email creates:

• missing attachments,
• outdated versions,
• and no clean audit trail.

Instead, use one request link and track status in one place.
That’s the whole point of tools like GetW9: less chasing, more certainty.

Rule 3: Clean your vendor list before the “deadline week”

Most teams clean vendor data when panic is already high.

Flip it. Do a cleanup when you’re calm, not when you’re rushed:

• merge duplicates,
• fix legal names,
• confirm entity type,
• make sure addresses are complete.

Rule 4: Use reminders with a real escalation ladder

Vendors respond when your process is clear.

A simple ladder works:

1. friendly request
2. friendly reminder
3. firm reminder with deadline
4. escalation (policy language)

Keep it polite, but make it real.

Copy-paste: The W-9 Cleanup Checklist (your fast fix)

Use this checklist as your “post-season reset.” It’s short on purpose.

A) Vendor list cleanup (30 minutes)

• Export your vendor list from your accounting system
• Sort by similar names and emails (this reveals duplicates fast)
• Merge duplicates into one vendor record
• Standardize names (legal name in the vendor record)
• Flag incomplete fields (address, tax class, entity type)

B) W-9 status audit (45 minutes)

• Filter vendors paid this year (or expected to be paid)
• Mark each vendor as: W-9 on file / requested / missing
• Check the W-9 is readable and signed
• Confirm legal name + TIN match what’s in your system

C) Chasing workflow (30 minutes)

• Send request #1 (simple + friendly)
• Send reminder #2 (clear next step)
• Send reminder #3 (deadline + consequence language)
• Assign one owner to track completions daily

D) Storage + access (15 minutes)

• Store W-9s in one secure place (not email)
• Limit access (AP + controller + admin only)
• Keep submission history (so you can prove when it was collected)

This checklist is a core part of the W-9 and 1099 playbook because it turns chaos into steps.

The short debrief meeting

Run this meeting right after the busy week, while the pain is fresh:

1. Where did we waste the most time?
2. Which vendors were hardest to collect from and why?
3. How many vendors were missing W-9s in the last two weeks?
4. What rule will we enforce next year?
5. Who owns the workflow end-to-end?

Write the answers down. Otherwise, you’ll repeat the same season.

Where GetW9 fits (simple and practical)

If your W-9 process is spreadsheet + email chasing, you’re choosing stress on purpose.

GetW9 makes the W-9 and 1099 playbook easier to run because it gives you:

• one link to request a W-9,
• automatic follow-ups,
• a clear completion status,
• secure storage with submission history,
• and a cleaner handoff to filing workflows.

The goal isn’t “more software.”
The goal is a process that doesn’t collapse in January.

Final takeaway

The teams who stay calm in tax season aren’t “more disciplined.”
They’re more prepared.

Use this W-9 and 1099 playbook now right after the rush so next year you can answer that scary January question without hesitation:

“Yes. We’re good. It’s already handled.”