Most law firms evaluate AI vendors by watching demos and reading marketing materials. That's how you end up with a $200,000 annual subscription to a tool that 3 attorneys use and nobody can explain the ROI on.
A structured RFP process isn't bureaucracy — it's the difference between selecting a vendor based on evidence and selecting one based on the best sales presentation. This template gives you the exact questions to ask, the evaluation criteria that matter, and a scoring methodology that turns subjective impressions into objective comparisons. Use it whether you're buying your first AI research tool or replacing your entire legal tech stack.
The 7 RFP Sections Every Legal AI Evaluation Needs
Your RFP should cover seven areas, in this order. 1. Company Background and Viability — how long they've been in business, funding status, legal-specific customer count, and financial stability. AI vendors are failing at a high rate; you need to know your vendor will exist in 2 years. 2. Product Capabilities — specific features mapped to your use cases, not a feature list. Ask them to demonstrate how they handle your workflows, not theirs. 3. AI Model and Training Data — what models power the tool, how they're trained, what data was used, and how accuracy is measured. 'We use AI' isn't an answer. 4. Security and Compliance — SOC 2 Type II, data residency, encryption standards, privilege preservation, and regulatory compliance. Non-negotiable for legal. 5. Integration and Implementation — how it connects to your existing tools, implementation timeline, required IT resources, and ongoing maintenance. 6. Pricing and Total Cost of Ownership — license fees, implementation costs, training costs, and ongoing support fees. Get a 3-year total, not just year-one pricing. 7. References and Case Studies — specifically from firms of similar size, practice mix, and technology maturity. A Fortune 500 corporate legal reference is useless if you're a 50-attorney litigation firm.
The 25 Questions That Separate Good Vendors From Great Ones
Beyond the standard RFP sections, these questions reveal what marketing materials hide. On AI accuracy: 'What's your measured accuracy rate for [specific task], and how do you calculate it? Provide test results, not self-reported numbers.' On data handling: 'Is our data used to train or improve your models? Can we opt out? Is that in writing?' On privilege: 'How do you ensure attorney-client privileged information entered into your system maintains privilege? What's your legal opinion on this?' On failure modes: 'Show us examples of when your AI gets it wrong. What does a bad output look like, and how does the system flag it?' On dependency: 'What happens to our data and workflows if we cancel? What's the exit process, timeline, and cost?' On roadmap: 'What features are planned for the next 12 months? How much of your current product was built in the last 6 months versus the last 2 years?' (This reveals whether the product is mature or still being figured out.) On support: 'What's your average response time for critical issues? Do we get a dedicated support contact or a ticket queue?' On uptime: 'What was your actual uptime over the past 12 months? Not your SLA target — your actual performance.' These questions make vendors uncomfortable. That's the point. The ones with good answers welcome the scrutiny.
Evaluation Criteria and Scoring Methodology
Don't evaluate vendors holistically — you'll default to whoever gave the best demo. Use a weighted scoring framework. Functional Fit (35% weight): Does the tool handle your specific use cases? Score each use case 1-5 based on the structured demo. This is the heaviest weight because a tool that doesn't solve your problem is worthless regardless of other factors. Security and Compliance (25% weight): SOC 2, data residency, privilege preservation, regulatory alignment. Score pass/fail on non-negotiables, then 1-5 on depth of security posture. Ease of Implementation (15% weight): Time to deploy, IT dependencies, configuration complexity, integration quality. Score based on vendor's proposed timeline and reference feedback on actual implementation experience. Total Cost of Ownership (15% weight): 3-year total cost including hidden fees. Score on a cost-per-user or cost-per-matter basis for apples-to-apples comparison. Vendor Viability (10% weight): Funding, customer count, financial stability, product maturity. Score based on company background responses and independent research. Create a scorecard with these categories, assign scores after each vendor's structured demo, and have 3-5 evaluators score independently before comparing. The vendor with the highest weighted score wins — regardless of who gave the most charismatic presentation.
The Structured Demo: How to See What Vendors Don't Want to Show
Never let a vendor run their standard demo. They'll show their best features on their best data in their best scenario. Instead, create a structured demo protocol. Prepare test scenarios based on your actual workflows. If you're evaluating a contract review tool, provide 5 real contracts (redacted if needed) and ask each vendor to process them live. If you're evaluating a research tool, prepare 5 research questions you recently worked on and compare the AI's output to your known-good answers. Require live processing. Pre-prepared demos are rehearsed performances. Ask vendors to process your test scenarios in real time during the demo. You'll see actual processing speed, actual error handling, and actual user experience — not a curated walkthrough. Include edge cases. Give vendors at least one scenario that's designed to be difficult — a contract in unusual format, a research question with nuanced jurisdictional variation, an invoice with subtle billing violations. How the tool handles edge cases tells you more than how it handles the easy stuff. Have end users present. The attorneys and paralegals who'll use the tool daily should be in the room asking questions. Their impressions matter more than the evaluation committee's because they'll determine adoption.
Vendor Comparison Framework: Making the Final Decision
After scoring, you'll likely have 2 vendors within 10% of each other. Here's how to break the tie. Conduct reference calls. Don't just ask for references — ask for references at firms similar to yours in size and practice mix. Ask references three specific questions: 'What was the actual implementation timeline versus what was promised?', 'What's the one thing you wish you'd known before buying?', and 'Would you buy this product again?' Run a paid pilot. Most vendors offer 30-90 day trials. Use them with real workflows and real users, not a sandbox environment. Measure the same success criteria you'll use for full deployment. A 60-day pilot at $5,000-$15,000 is cheap insurance against a $150,000 annual mistake. Negotiate from strength. Once you've completed the evaluation, you have leverage. Share (anonymized) competitive pricing with your preferred vendor. Ask for a 90-day termination clause for the first year. Request implementation support at no additional cost. Negotiate annual rate caps. The vendors who won't negotiate on reasonable terms are telling you something about how they'll treat you as a customer.
The Bottom Line: A structured RFP process turns AI vendor selection from a beauty contest into an evidence-based decision. Cover 7 sections, ask the 25 hard questions vendors don't want to answer, score with a weighted framework (Functional Fit 35%, Security 25%, Implementation 15%, Cost 15%, Viability 10%), require structured demos with your real data, and run a paid pilot before signing an annual contract. The process adds 3-4 weeks to your timeline. It prevents $150,000+ annual mistakes.
AI-Assisted Research. This piece was researched and written with AI assistance, reviewed and edited by Manu Ayala. For deeper takes and the perspective behind the research, follow me on LinkedIn or email me directly.
