Missing Items: Using AI to Build the Client Request List

A client request list is a list of absences. Every line on it is something the Preparer expected to find in the folder and didn't. So an AI tool can draft it only against a written list of what the Firm expects. Without that list, any "missing" row the tool returns is a guess.

Work in a set order: write down what you expect, run the pass on a copy of the folder, check every row yourself, then send the client one plain request.

For pulling and citing figures from what is in the folder, see the citation piece.

Start with the expected-documents list

Build it per client, before any tool sees the folder, from two sources: last period's file list, and what the engagement says changed this period.

List every document in the prior period's final folder by what it is and which account or payer it covers, not by file name. Then go through the engagement notes and intake answers and adjust for each change. For each new account, property sale, or new state, identify the documents your Firm needs for this engagement and record why. For a closed account, check which documents are still needed for this engagement before removing an item, and record the reason for your decision.

Give every line an ID and a plain reason, such as "in last period's file" or "engagement note: new account." Have the tool cite that reason back.

A short example for a made-up client, Jane Doe, who owns a made-up entity, Doe Holdings:

• E1. Wage statement from Jane Doe's employer. Reason: in last period's file.
• E2. Period-end statement for Jane Doe's bank account. Reason: in last period's file.
• E3. Statement for the brokerage account Jane Doe opened this period. Reason: engagement note, new account.
• E4. Sale paperwork for the rental property Jane Doe sold, including the closing statement. Reason: engagement note, sold property.
• E5. Payroll records for the employee Doe Holdings hired in a new state. Reason: engagement note, new state.
• E6. Monthly bank statements for Doe Holdings. Reason: in last period's file.
• E7. Statement for Jane Doe's old savings account. Reason: engagement note, account closed. Confirm which records are needed for this engagement before deciding whether to request it.

Point the tool at a copy of the folder

Two vendors describe file access this way. Claude's help article for Cowork says: "On desktop, Claude can read from and write to your local files without manual uploads or downloads." OpenAI's ChatGPT quickstart says: "ChatGPT can read and modify files in the folder you choose." Neither statement says how a tool handles a missing-items pass, so test that before the Firm relies on it.

Both quotes say the tool can change files, not only read them. So make a copy of the client folder, point the tool at the copy, and leave the original alone. The original stays the record of what the client sent. Use only a tool and a setup the Firm has approved for client data.

Tell the tool to read every file in the copy and list each file it read, with page counts and any page it couldn't read. Compare that list with the folder's own file list first. If a file is missing from the tool's list, treat every row that could depend on it as unchecked. The failure-modes piece shows how to test a tool for skipped files and filled blanks.

The instruction for the missing-items pass

Paste the expected list into the instruction and ask for one row per item, with one of two answers:

• Found: the file name and the page where the item appears.
• Not found: the ID and the reason from the expected list.

Add three rules. Never infer that an item exists from a mention in another document; a bank statement showing a transfer from a brokerage account is not the brokerage statement. Never fill in a value, an estimate, or a placeholder for a not-found item. And list separately any file in the copy that matches no expected item.

Read that last list. A document for an account nobody mentioned belongs on that list; add it to the expected list with its reason.

Check the draft list by hand

The tool's output is a draft. The Preparer owns the list.

1. Open the folder for every not-found row. Look at scanned pages, image-only files, and anything added after you made the copy.
2. Open the cited page for every found row. Confirm the right person or entity, account, and period.
3. Strike rows the client already answered another way, such as a document sent by mail or a reply saying the item doesn't apply. Note where each answer came from.
4. Add anything you know that the list lacks, such as something the client said on a call or a note from last period's review. Give each added row its reason.
5. Initial each row you've checked.

Turn it into one client request

Send the client one request, written only from the checked list.

• One line per item, named the way the client knows it: "the statement for the brokerage account you opened," not an internal code.
• Why you need it, in the client's terms.
• No jargon, no form names, and no IDs from the expected list.
• One reply path, the one the Firm already uses, such as its client portal.
• A line asking the client to say so when an item doesn't apply. That answer closes a row too.

A short sample for Jane Doe:

Hi Jane,

I'm working on your file and still need four items. Please upload each one to the client portal you already use. If an item doesn't apply to you, reply in the portal and say so.

1. The statement for the brokerage account you opened. I haven't found the statement for this account in the documents received. I need it to review the account's activity for this period.
2. The paperwork from the sale of your rental property, including the closing statement. I need it to show what you sold.
3. Payroll records for the employee Doe Holdings hired in the new state. I need these records to understand Doe Holdings' payroll activity in that state.
4. The monthly bank statements for Doe Holdings. I need them to see the account's activity for the whole period.

Thank you,

Alex Doe

After the client replies

Make a fresh copy of the updated folder and run the same pass with the same instruction and updated expected list. Close each open row with the file that answers it, or with the client's reply saying it doesn't apply, and check each closed row by hand. Rows still open go into the next request, and only those.

Keep the record with the workpaper, so the Reviewer can trace each document to the row that asked for it: the expected list, the tool's file list, each draft, your checks, the request you sent, and what closed each row. See for reviewers for what a Reviewer checks. The Reviewer reads finished entries back to their pages later; see the readback piece.

The Firm decides whether to use an AI tool's pass for this task and which checks to require. The Reviewer concludes and signs off on the workpaper.

A one-screen missing-items checklist

Fit this to your Firm's own steps first.

1. Build the expected list from last period's file list and the engagement notes, with an ID and reason per line.
2. Copy the client folder and point an approved tool at the copy only.
3. Compare the tool's list of files read with the folder's file list.
4. Ask for found (file and page) or not found (ID and reason) for each item.
5. Forbid inferring items or filling values.
6. Open the folder for each not-found row and the cited page for each found row.
7. Strike answered rows, add known ones, and initial each checked row.
8. Send one plain request with one line per item and one reply path.
9. Rerun on a fresh copy after the reply, close each row, and keep the record with the workpaper.

Where TracePrep fits

In TracePrep's Reasonable Compensation Study, every figure traces to its source, occupation, geography, and period, at field level. A Reviewer signs off on each Study, and the audit log records who prepared it, who changed what, and who approved it. Finalized evidence stays with the Firm.

This is general information, not tax or legal advice. Your licensed professional and your Firm's Reviewer are responsible for every return and every conclusion. Keep client data inside the systems your Firm has approved. As general guidance only, not advice: if you use an AI tool with client data, firms generally look for a business or commercial plan whose terms cover how that data is handled; read the vendor's current terms before you do.

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