Short answer: the best document chase is specific. Let AI compare what each client has sent this year against what they sent last year, list the gaps, and draft a short request that names each missing item. A person on your staff reads it and sends it. The software does not decide what the client needs to file.
If your firm has an AI policy, this is a good first use to put under it. The data is your own client file. The output is a draft. And it shows why AI does not replace accountants: it removes the hunting, not the judgment.
Why the chase eats the season
Every firm knows the pattern. A general "please send your documents" email goes out. Half the clients send something. Nobody knows what is still missing until a preparer opens the file and finds no brokerage statement, no K-1, no childcare receipts.
Then the reminders start. They are vague, so the client sends the wrong thing, or nothing. The deadline gets closer. Extensions go out that did not need to.
What AI may do
- Read last year's file. Which forms came in: W-2s by employer, 1099s by payer, K-1s by entity, mortgage interest, property tax, charitable receipts.
- Read this year's uploads. Match what arrived against that list.
- List the gaps by client. "Last year: 1099-DIV from two brokerages. This year: one."
- Draft a specific request. Names the payer, the form, and where the client might find it. Short and polite.
- Flag changes for a person. A new employer, a K-1 that stopped, a rental that disappeared. Those may be real changes, not missing paper.
What it must never do
- Decide the client no longer needs a form. A missing K-1 might mean a sold interest. Or it might mean the client forgot. Your staff asks.
- Give tax advice in the request. "You don't need to file that one" is not a reminder. It is advice.
- Send on its own. Every request goes out from a person, from your normal portal or email.
- Put client files in a public chatbot. Tax information has its own rules on use and disclosure. Keep the comparison inside systems your firm controls, and ask whether it can run on your own hardware.
How staff run it
- Each week, the gap list arrives with a draft per client.
- The staff member who owns that client reads it. Edits anything that looks wrong.
- Approved requests go out through your portal or email.
- When documents arrive, the list updates. Clients who are complete drop off.
- Anything flagged as a "change" goes to the preparer before the next reminder.
The point is that every reminder says exactly what is missing. Clients answer specific questions faster than vague ones.
Questions to ask before you turn it on
- Can it read last year's file and this year's uploads from the systems you already use?
- Does it show why it thinks something is missing? The prior-year document should be one click away.
- Can it send anything without a person? You want no.
- Where does the data go during the comparison? Ask about retention, training, and an on-premises option.
A realistic first step
Pick ten returning clients who were late last year. Run the comparison for them. Have the staff member who chased them read the gap lists. If the lists match what she remembers chasing, you have saved next season's hardest month.
If you want a document chase that drafts from your own files and leaves the sending to your staff, talk with us. If your portal's checklist is enough, we will say so.
Related: Writing an AI policy for an accounting firm · our approach for accounting firms.