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Module 5 For Accounting intermediate 45 min

Systematize Your 1099 / W-9 Season

The win is the documented workflow, not the one-off.

Systematize Your 1099 / W-9 Workflow

Every year the same scramble: collect W-9s, categorize payments, hit the filing thresholds, and beat the deadline across dozens of clients. You want this to run the same way every time, with AI doing the legwork and human checkpoints on anything that triggers a filing. This builds a documented, repeatable workflow a staff accountant can run, with thresholds you confirm against current IRS guidance.

Recommended tool

claude

Strong at decomposing a seasonal scramble into clean steps and writing the SOP. It structures the workflow; you confirm every threshold and filing rule against current IRS guidance, because tax thresholds change.

Bring to the exercise

  • The steps you currently take when 1099 season starts (however messy)
  • Where the filing, threshold, and deadline decisions live
  • Your Practice Context Document
Step 1

Map What You Do Today (no cleanup)

Capture the real process before improving it.

What to substitute before pasting

  • [DESCRIBE YOUR MESSY STEPS] Your actual 1099/W-9 process, in whatever order it happens, no cleanup.
Here is my Practice Context Document:
[PASTE YOUR PRACTICE CONTEXT DOCUMENT]

Roughly what I do when 1099 season starts:
[DESCRIBE YOUR MESSY STEPS]

Ask me clarifying questions, then play it back as a numbered list. Do not improve it yet. Capture it accurately.
What good output looks like
  • Plays your process back accurately.
  • Asks before assuming any step.

Verify before using AI's output

Step 2

Decompose and Route

Split the process into steps, each routed to human or the right tool.

Turn this into a clean workflow. For each step give me:
- The step name
- Whether it is human or AI
- If AI, which tool (NotebookLM for reading documents, Claude for drafting, a spreadsheet for tracking)

Mark the pure-judgment steps that stay mine.
What good output looks like
  • Each step is routed to human or a named tool.
  • Judgment steps are flagged as yours.

Verify before using AI's output

Step 3

Gate Every Filing and Threshold Step

Put a human checkpoint before anything that triggers a filing.

Identify every step where a threshold, a filing, or a deadline is decided.

Insert a HUMAN CHECKPOINT before each one. At each checkpoint, state that the person must confirm the current IRS filing threshold and deadline against official guidance for the relevant tax year, because these change. Do not state a specific dollar threshold or date as settled fact.
What good output looks like
  • Filing and threshold steps are gated.
  • Each checkpoint says to confirm current IRS guidance, not a hardcoded number.

Verify before using AI's output

Step 4

Write the SOP

Produce a one-page SOP a staff accountant can run the same way every year.

Write a one-page SOP a staff accountant could follow the same way every season:
- Numbered steps
- The tool for each step
- The prompt to use at each AI step
- Human checkpoints in bold, including the "confirm current IRS threshold and deadline" checks

Plain language.
What good output looks like
  • A runnable SOP with the prompts embedded.
  • Human checkpoints stand out in bold.

Verify before using AI's output

Step 5

Stress-Test the Workflow

Find where it breaks and confirm the human catch.

Where will this workflow break? Think: missing W-9s, a vendor who should have gotten a 1099 but was missed, a payment miscategorized, a client who sends data late.

For each failure point, name the human catch. What did I forget?
What good output looks like
  • Names real failure points, not generic ones.
  • Pairs each risk with a human catch.

Verify before using AI's output