Enhancing Document Review with AI Checklists

What document review against a checklist is

Document review against a checklist is a method to compare a document with a written list of requirements. For each item on the list, the reviewer records one result: present, missing or unclear. The reviewer also records where in the document the evidence is.

The method has three parts:

1. The checklist: the items that must be present, the items that must not be present and the quality rules.
2. The document: an invoice, a contract, a resume, a photo, a proposal or another file.
3. The reviewer: a person who goes through the list item by item, or an AI model that does a first pass for a person.

A checklist changes the question. Without a checklist, the reviewer asks “does this look right?” The answer depends on the experience and the attention of that reviewer. With a checklist, the reviewer asks “is item 4 in the document?” Two reviewers with the same checklist usually get the same answer.

Examples of checklist items

The method is the same for all document types. Only the items change:

Document	Example checklist items
Invoice	Invoice number, date, seller and buyer details, line items, tax, total, payment terms, PO number
Contract	Scope, payment terms, termination, liability limit, governing law. Must not have: automatic renewal without notice
Resume	Each must-have requirement of the job, consistent dates, results with numbers
Product photo	Background color, size in pixels, share of the frame that the product fills, no text or logos
Proposal	An answer to each requirement of the request for proposal (RFP), page limit, required forms and signatures

How to write a good checklist

• Make each item specific. “Payment terms state the amount, the due date and the payment method” is specific. “Contract is complete” is not.
• Make each item testable. A reviewer must be able to answer present, missing or unclear without an opinion.
• Mark each item as required or optional. Then a missing optional item does not block approval.
• Add items that must not be present. For example: no unlimited liability, no watermark on the main photo.
• Group the items by section, for example parties, money, dates, legal terms and signatures.
• Name the source of each rule if it comes from a law or a platform. Then you can find out when the rule changes.
• Keep the list short. If a checklist has too many items, split it into one list for each document type or each part.
• Test the checklist on three or four real documents. If it misses a known problem, add an item. If an item gets different answers from different reviewers, rewrite it.
• Read the checklist again when a rule, a policy or a vendor changes.

How to review a document by hand

1. Open the checklist and the document side by side.
2. Go through the items in order. Do not jump to the items that interest you.
3. For each item, write present, missing or unclear.
4. For each present item, write the page, the section or the line where you found it.
5. For each unclear item, write the question that you must ask.
6. If an item must not be present and you find it, mark it as a problem and quote it.
7. At the end, list the missing items and the problems. Send that list to the author of the document.
8. Write down each decision on an unusual case. Use the same decision the next time.

How to do a checklist review with Claude or ChatGPT

An AI model such as Claude or ChatGPT can do the first pass. It reads a long document fast, and it can find an item when the document uses different words. For example, it can match “net thirty” with “payment due within 30 days”. The method stays the same. You give the checklist and the document, and the AI gives a result for each item.

1. Write the checklist first. Do not ask the AI “is this contract OK?” Give it the exact items.
2. Remove personal, financial and confidential data that the review does not need.
3. Make sure that the data settings of your AI workspace permit you to upload the document.
4. Paste the checklist into the chat, and attach or paste the document.
5. Ask for a result for each item, with a quote from the document as evidence.
6. Find each quote in the document yourself.
7. If the AI marks an item as missing, but the document uses other words, add those words to the item.

This prompt works for most document types:

Below is my checklist and a document. Go through the checklist one item
at a time. For each item, answer "present", "missing" or "unclear".
For "present", quote the exact text from the document and give its page
or section. For "unclear", say what is ambiguous. Do not add items that
are not on the checklist. At the end, list all missing and unclear items.

Do not accept a finding without a quote that you can find in the document. An AI model can miss an item, and it can report text that the document does not contain. Use the AI result as a list of things to look at, not as the final review. For legal, tax or hiring decisions, a qualified person must make the final decision.

Common mistakes

Mistake	Result	Correction
Vague items	Reviewers answer the same item differently	Rewrite each item as a test with a yes or no answer
No “must not be present” items	Bad clauses or content pass the review	Add the red flags to the list
Old checklist	The review passes documents that break new rules	Read the checklist again when rules change
Results without evidence	Nobody can find the evidence for a “present” result later	Record the page, the section or a quote
AI result used as the final answer	Invented or missed items go through	Find each quote in the document yourself
Exceptions not recorded	The same case gets a different decision next time	Write down each decision and its reason

How to measure the result

Track a few numbers for each document type. Count how many documents you review. Count how many pass on the first submission. List the reasons for failure and how often each one happens. Measure how long a review takes. If the same item fails often, fix it at the source. For example, add the field to the invoice template or the clause to the contract template.

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