Tips for Effective Use of AI in Contract Drafting

Original LinkedIn post here.

Tips for Effective use of AI in Contract Drafting

The warning 'this model can make mistakes' is hard-coded in the interface of the LLMs for a reason. Here are some tips to help mitigate the risk when using AI to draft and review contracts.

1. Rotate each task through multiple models. Paste the same prompts into Anthropic, ChatGPT and Gemini as you go. Models change constantly, even from one session to the next, so three perspectives help with quality control and completeness.

2. Work section by section. AI struggles with how provisions interconnect. A definition of "Confidential Information" may undercut a carefully constructed damages cap for data breach, but AI won't notice. Section-by-section review keeps both you and the AI focused on getting each piece right before moving to the next.

3. Set the pace. The chat format and AI's tendency to assume you're in a rush work against the flow state you need when working through long, complex documents. Set your own pace.

4. Keep the context window small. Upload the agreement you're working on, but trim unnecessary exhibits or comparison examples. AI processes text statistically and can get overwhelmed by the noise. Rotate reference materials in and out rather than dumping everything at once.

5. Be active and iterative in your prompting. Iterate as you go rather than relying on a single master prompt. Give context to fix misunderstandings and stay focused on what is coming up in the analysis, instead of front-loading long rule lists.

6. Be creative in your prompting. Assign a "red-team" role to act as opposing counsel, probing for ambiguities and vulnerabilities. Run a trace through critical mechanisms (warranty → indemnity → limitation of liability). Ask for targeted audits of definitions, cross-references, and surviving sections. This is where AI really shines: you can run any check or test you think of and get hits you might not otherwise see.

7. Continually remind yourself that AI cannot think or reason. We don't yet have good language for what AI is doing, but it's not thinking. You're flinging ideas against a math table trained to sound helpful and authoritative. But obsequiousness is the last trait you'd want in a thinking partner. Don't let it decide issues for you.

8. Use PDFs. Automatic numbering in Word documents baffles AI. Just upload the PDF.

9. Show it to another human. At my old firm, everything needed two sets of eyes before it went out: guidance emails, checklists, agreement drafts. No exceptions. Now I get to show every draft to 120 lawyers on the Bonterms Committee. AI is not a colleague or a replacement for one. Always get another human to review before you hit send.

Brought to you by your friends at Bonterms. Bonterms Standard Agreements are free-to-use, neutral agreements vetted by our 120-lawyer Committee and cover the full range of IT procurement transactions. The Bonterms Platform is the fastest, easiest way to get a deal done on a Bonterms Standard. Learn more: bonterms.com.