Key Takeaways:
- Predict your counterparty’s perspectives with AI prompts that can eliminate your blind spots and help you anticipate sticky negotiation points.
- Quickly draft powerful cover emails that clearly articulate the critical components of each contract to accelerate and systematize necessary internal approvals.
- Leverage AI to eliminate hours of tedious proofreading without worrying if you missed something.
Great contract drafting requires more than traditional expertise. Even well-crafted agreements can harbor hidden vulnerabilities that lead to disputes and challenges to their enforceability.
You can leverage AI tools to proactively identify and address vulnerabilities, counterparty objections, and communication needs during drafting. Thus, you can generate more resilient agreements while saving time and advancing your company’s business. Win!
First, a note on tools: the AI prompts discussed here are compatible with any generative AI tool. However, outputs may vary based on the AI tool. Use the examples provided to compare your results.
1. Use AI to See Through Your Counterparty’s Eyes
Because you view contracts from your party’s side, it can be difficult to anticipate the counterparty’s objections. After all, your position is the most logical one, right? One of the most effective ways to strengthen contracts is to anticipate how the other side will challenge your terms. You see what they’ll ask about, maybe you make your position more palatable (or word it better to protect what you actually need to protect), and you prevent a redline – ultimately getting deals done faster for your business while still at the right level of risk. AI can provide a level of objectivity that will yield fresh perspectives, enabling you to incorporate acceptable language in the first draft and reduce the time to final agreement. You’re using AI’s chameleon-like quality – i.e. the fact that you can tell AI who to be, and it will do that – to your advantage. Almost like a mock trial before a real trial. In both cases, you’ll perform better having done it.
This AI prompt transforms your perspective by having the tool roleplay as the opposing party, identifying terms they’ll want to negotiate.
The Prompt: “Take the role of the legal counsel for the other party for my company’s contract attached or linked below. [Upload or link to contract] Review the contract from the perspective of the legal counsel of the other party. 1. Create a table of the top 5 issues that you would want changed or negotiated, an explanation for each, and the exact language and section number giving rise to the issue. 2. Pretend you are the other side, and write me an email negotiating those 5 issues. Be detailed in your email.”
Real-World Application: Assume you drafted an employment agreement for your company and a new executive, John Doe. You like your terms but need to anticipate John’s potential objections to reduce the negotiation cycle. The Counterparty Reads Your Contract prompt can provide a comprehensive list of John’s possible objections. It can also produce a sample letter from John’s attorney, with proposed revisions.
Time-Saving Applications & When to Use: Deploy this prompt before sending any significant agreement to proactively address likely objections and decide where you will and won’t negotiate. It’s particularly valuable for high-stakes deals where anticipating objections can prevent lengthy negotiation cycles.
2. Streamline Approvals with Consistent Key Summaries
It’s good practice to require VP+ approval for signing, maybe based on spend thresholds or other criteria you’ve set as a legal team. Yet getting executive sign-off often creates bottlenecks when busy leaders lack time to review entire agreements. Or, probably worse, execs sign without really reviewing. This prompt generates comprehensive cover emails that distill complex contracts into digestible summaries with clear recommendations from Legal. The result? The execs on the business side get the info they need, feel good about approving (or not), and business moves faster and more effectively. Win.
The Prompt: “I am attaching a draft agreement. I need a cover email for when I send the agreement to an executive for final approval and signature. [Attached. Use citations.] I’d like to provide the target exec with an email that explains: 1. a short paragraph on what the agreement is and why we are asking for signature (including which party we are), 2. the major things our company is committing to under this agreement, and the major things we receive (commercial terms), 3. risks of which they should be aware (for example, if the agreement is difficult to terminate or there are unusual legal terms), 4. A final recommendation of why it’s good or not good to sign. Include something they might doubt and ask me about.”
Real-World Application: Assume negotiations with John Doe have concluded, and you now need your executive’s sign-off. This prompt illuminates the critical information your executive needs. Not only do you provide a clear and concise outline of the key terms of the agreement to be signed, but the Approval Cover Email prompt enables you to consistently replicate this process.
Time-Saving Applications & When to Use: This prompt eliminates manual executive summary creation and ensures you include all critical decision-making elements. Use the prompt for any agreement requiring approval, particularly complex deals, vendor agreements, or partnerships, where executives need a quick but thorough understanding instead of reading entire agreements or asking for explanations.
3. Improve Contract Quality with Systematic AI Review
Even experienced attorneys can miss technical errors that undermine contract enforceability. This comprehensive prompt systematically reviews agreements for consistency, completeness, and potential issues that human reviewers often overlook.
The Prompt: “CONTRACT: Attached. Review the attached contract thoroughly. Provide an introductory paragraph explaining the basic purpose and function of the contract. Create a table with columns for Emoji, Criterion, Assessment (
needs review, 
potential issue, or 
compliant), and Evidence with exact provisions and section numbers. Evaluate based on: spelling mistakes, grammatical issues, whether capitalized terms are properly defined, and any abruptly ending sentences or sections. For each issue found, add a new row to the table. Look very hard for as many issues as possible. After addressing the above criteria, identify any unusual or standout elements compared to similar agreements in a separate table using the same structure. Ensure your review is extremely thorough and comprehensive.”
Time-Saving Applications & When to Use: This Contract QA prompt replaces hours of manual proofreading with a systematic 5-minute review using visual assessment (emojis) for instant issue prioritization and exact citations for quick fixes. Deploy before finalizing any agreement, especially complex documents with multiple schedules, template updates, tight deadlines, or multi-editor situations. Catch problems during drafting when fixes are simple and cost-free, rather than during negotiations or enforcement.
Retain Your Human Element
AI can dramatically reduce review times and enhance analysis, but it cannot replace human judgment. Only you understand your company’s risk tolerance, strategic priorities, and business relationships. You know the communication style that resonates with executives and what drives their decisions. Pro tip: use the three prompts above as your base.
The most effective contract review combines AI’s speed with human wisdom about what matters most. In this partnership, you remain the architect while AI serves as a sophisticated tool — powerful, precise, and dependent on the skilled professional wielding it.
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