Key Takeaways:
- AI contract review tools are most powerful when they are directed by a contracts expert — not the other way around.
- The Oreo Cookie Method is a five-step, tool-agnostic framework that integrates AI into the contract redlining process without sacrificing the attorney’s judgment, context, or strategic thinking.
- When human expertise and AI work together in the right structure, the result is faster, more consistent, and higher-quality contract review than either could produce alone.
Here’s something I think about a lot: what does truly great contract review actually look like in 2025?
Because the answer has changed. Not completely. The fundamentals of good redlining haven’t gone anywhere. You still need to understand the deal, identify the important issues, and communicate your positions clearly and persuasively. As I’ve written about in Contract Redlining Etiquette, redlines are (and still are) an important and necessary component of the deal negotiation.
But the tools available to us have expanded in a meaningful way. Today’s AI contract review technology is genuinely useful, and the lawyers and contracts professionals who are getting the most out of it are the ones who have figured out how to integrate it thoughtfully — not as a replacement for their expertise, but as a force multiplier for it.
That’s exactly what the Oreo Cookie Method is designed to do.
I developed this framework while rolling out an AI contract review tool for my legal team. The question I kept coming back to wasn’t whether to use AI. It was how to build a contract redlining workflow that brought out the best in both the technology and the people using it. One where the attorney’s judgment and experience stayed at the center, and the AI amplified what they could do — not the other way around.
The result is a five-step redlining workflow that I believe represents the ideal combination: human expertise and AI working together, each doing what it does best.
Why the Combination Matters
There’s a version of AI-assisted contract review that works really well, and a version that doesn’t. The version that doesn’t work is when lawyers treat the AI as the reviewer and themselves as the approver. The version that works is when lawyers treat the AI as a highly capable tool they are actively directing — one that covers ground faster, flags issues more consistently, and frees them up to focus on the judgment calls that actually require a contracts expert.
The distinction matters because what makes a contracts professional valuable has never been the ability to read a contract slowly. It’s the ability to understand what a deal means, assess risk in context, and craft redlines and comments that move a negotiation forward. Those are human skills. They require legal training, pattern recognition built over years, and situational judgment that no playbook — human-built or AI-generated — can fully capture.
If AI contract review tools are designed to be used by contract experts, then the expertise is the point. The Oreo Cookie Method is built around this truth. It’s not a workaround for AI’s limitations. It’s a workflow that’s specifically designed to bring the best of both worlds to every contract review.
The Oreo Cookie Method
The name does the explaining. Two attorney-driven reviews serve as the cookies: the solid, substantive layers that hold the whole tasty treat together. The AI-assisted steps in the middle are the cream filling: doing real, valuable work, but only at their best when surrounded by the human layers on either side.
The method is completely tool-agnostic. It works with any AI contract review platform (including AI prompts and custom GPTs designed for contract reviews) and is built around a principle rather than a feature set. The attorney goes first, the attorney goes last, and the AI works in between, under the attorney’s direction. Here are the five steps of the Oreo Cookie Method:
Step 1 — Attorney Review #1:
Context and comprehension (the first cookie). Your workflow starts exactly as it always has. Review the assignment in your contract management system, gather the context you need from your business stakeholders, and read the agreement from beginning to end. This is the first cookie — the non-negotiable foundation. The AI will work faster and more accurately when it’s being directed by someone who already understands the deal, the relationship, and what actually matters in this particular negotiation. Context is something the attorney brings. No tool can replicate it.
Step 2 — Playbook: Issue spotting (the start of the filling).
Now you bring in the AI. Run your company-built playbook against the third-party template. A well-built playbook reflects your organization’s risk tolerances, preferred positions, and standard fallbacks. The AI surfaces flagged issues and recommended changes — and you decide what to apply, what to adjust, and what to set aside. This is a tailored, high-efficiency first pass that gets the most important issues on the table quickly.
Step 3 — Review: Diving deeper (more filling).
Use your AI tool’s general review feature to run a second pass on the current draft from your party’s perspective. This step catches what the playbook wasn’t designed to catch — general legal concepts, jurisdiction-specific considerations, and anything that falls outside your standard template. Think of it as a well-read colleague doing a second set of eyes. You still evaluate everything it surfaces.
Step 4 — Ask: Targeted cleanup (the last of the filling).
This is the most surgical step. Use the AI’s prompt-based features for specific, defined tasks: cleaning up defined terms, correcting cross-references, and resolving open items. This isn’t a general sweep — it’s a deliberate layer of refinement driven by what you’ve already identified as outstanding. The attorney sets the agenda; the AI executes.
Step 5 — Attorney Review #2: Customize and finalize (the second cookie).
This is where the attorney’s expertise does its most important work. Review the redlines from top to bottom. Remove what doesn’t belong and sharpen what does. Write explanatory comments that are persuasive, contextually relevant, and genuinely reflect your judgment and strategy — not just a summary of what the AI flagged. Add internal notes, fill in the blanks, clean up the formatting, and confirm that every markup in the document reflects exactly what you intend. This is the second cookie, and it’s what separates a polished, strategic work product from a raw AI output.
The Ultimate Combination
What I love about this method, and why I think it represents the future of high-quality contract review, is that it asks both the attorney and the AI to contribute what they’re genuinely best at.
The AI brings speed, consistency, and coverage. It will move through a contract faster than any reviewer, flag issues against a playbook without getting tired, and catch things that might otherwise slip through on a dense, late-in-the-day review. Those are real advantages, and they matter.
The attorney brings everything else. The understanding of what the deal actually means. The judgment to know when the playbook position should be modified because of who you’re dealing with or what the relationship requires. The ability to write a comment that doesn’t just explain a redline but advances the negotiation. The instinct for which redlines to push on and which ones to let go.
The Oreo Cookie Method isn’t a compromise between human review and AI review. It’s what happens when you combine the two at their best.
Building this workflow also creates something that’s hard to achieve otherwise: consistency across your team. When everyone is following the same structure — same entry point, same AI steps, same final review standard — you get a much more uniform quality of work product, regardless of who ran the review.
I’ve said before that contract redlines are more than just markups. They are a negotiation tool. And the best negotiation tools are the ones that reflect both preparation and expertise. The Oreo Cookie Method gives you a structure to bring both to every contract you touch.
The filling is great. But it really does need the contract experts to hold everything together.
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