Chase missing tax documents with AI, for accountants

Tax season stalls when you have to open every client folder just to see who forgot their paperwork. AI compares each folder against your checklist and drafts a gentle nudge for each client.

What to gather first

Your standard tax document checklist
Links to this year's client folders
Two friendly reminder emails you sent before

Which app

For this one, AI needs to open your files itself, so use an agent app rather than a chat window. Three that a non-technical owner can install today:

Hermes AgentFree and open source. Runs on your Mac or PC, works inside a folder you choose. CodexOpenAI's agent app. Paid plan, polished, tied to their models. Claude CodeAnthropic's agent app. Paid plan, careful with permissions.

How to do it

Share the checklist and folders. Open your AI agent app. Give it your document checklist and access to the client folders for this tax year.
Let AI spot the gaps. AI looks through the files in each folder. It compares what is there against your checklist and lists what is missing for each client.
Ask for email drafts. AI drafts a short reminder note for each client with missing items. It matches the tone of your past emails and names the exact missing papers.
Review and send. Read through each draft on your screen. Fix any tax names, verify the missing items against your own notes, and send the emails yourself.

What to type first

Here is our tax document checklist, our sample reminder notes, and access to the client folders. Compare the files in each folder against the checklist. For every client missing records, draft a polite email naming the exact items we still need. Match the tone of my examples. Do not send anything to anyone.

Change the words to match your business. AI follows what you say, so say what done looks like.

Before you trust it

Make sure the client did not already email the missing file under a strange name.
Check that the requested documents match the client's actual filing type.
Verify that the tone sounds like your firm before you hit send.

Try having AI draft follow-up notes for clients who still have not replied by next week.

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