Using AI to Compare Documents

Using AI to Compare Documents

Avatar of author Jacob Beckerman

Jacob Beckerman

jacob@macro.com

Updated: 2025-02-10

One of things we’re asked most frequently at Macro, especially by lawyers, is how we expect AI to change the way documents are redlined, versioned, and compared.

Many legacy tools work to compare documents by ‘reading’ each word, character by character, and generating a document that attempts to merge those differences into once place. This approach works well for comparing two standard .docx documents with excellent, consistent formatting and similar layouts, but doesn’t work as well for documents that are different file types (.pdf vs .docx), organized in different ways, formatted oddly, etc.

AI does an excellent job of filling this gap, and can be used to compare many documents of different file types, even if those documents are ill-formatted, have sections in different pages, etc.

Right now, the output of an AI-generated document comparison looks a little different than legacy comparison tools which show differences in-line within a document itself. That’s because AI is still learning how to markup a document word-by-word, instead of doing wholesale deletions and insertions of full paragraphs. Once we at Macro are happy with AI’s ability to do in-line edits, we’ll make that feature available! For now, try out this prompt to compare documents that are similar in meaning, but not quite the same.

How and When to Use This Prompt

Use this prompt to compare the content many documents of varying file types. This prompt will output a table showing differences in language pulled from the document exactly.

This prompt was written with lawyers and finance professionals in mind. Change it up for your industry by modifying the topics (such as “economic terms”) to ones relevant for your field.

 

Prompt
Acting as the world's most thorough legal assistant, please analyze the provided agreements and create a detailed comparison by doing the following:

Please provide:
1. Brief Executive Summary (2-3 sentences highlighting key differences)

2. Comparison Table with these columns:
- Category/Topic
- Market Standard (if known)
- Document 1 (with section references)
- Document 2 (with section references)
- [Additional documents as needed]
- Key Differences
- Business/Legal Impact

Make sure to cover AT LEAST the following topics, but include ALL important differences using your knowledge as the world's best legal assistant and the content of the documents. 
1. Economic Terms
2. Covenants & Restrictions
3. Security/Collateral
4. Events of Default
5. Key Definitions
6. Reporting Requirements
7. Amendment Rights
8. [Other relevant categories based on document type]

For each category, please:
- Include exact language from documents. It must be taken exactly from the document. Include citations. 
- Highlight material differences
- Note market position (if unusual)
- Flag any high-risk variations
- Identify potential negotiation points

Please focus on differences that would matter to a lawyer or finance professional reviewing these documents. It is better to be over-inclusive than to forget things, as this is a legal document and a lawyer or other professional will be reviewing your output.