The AI RFP Checklist Every Founder Should Send in 2026
The 27 questions that separate real AI vendors from wrappers, and how to score responses.
Most AI RFPs are useless — they ask about "years of experience" and "similar clients." Here are the 27 questions that actually separate real AI teams from wrappers, plus how to score responses.
Capability (score 0–3 each)
- Share a production system you shipped in the last 12 months.
- Which LLM providers have you shipped with in production? How do you fail over?
- Describe your eval framework. What's in your golden set?
- How do you detect regressions before shipping a prompt change?
- How do you monitor cost per user per month?
Security + compliance
- Do you sign a BAA, DPA, and MSA?
- How do you isolate customer data across tenants?
- Do you retain prompts/completions? Where and for how long?
- How do you handle PII in prompts?
- Are you SOC 2 (or on the path)?
Delivery
- What is your typical MVP timeline?
- Do you commit to a fixed scope or T&M?
- Who is on the team and what's their day rate?
- What happens when scope changes mid-project?
- What's your handoff and documentation standard?
Cost transparency
- Break down build cost vs ongoing LLM cost.
- Estimate token cost per 1,000 end-users at expected usage.
- What does maintenance cost look like at month 6, 12, 24?
IP + exit
- Who owns the model weights, prompts, code, and evals?
- What happens to our data if we terminate?
- Are any dependencies proprietary or locked to your stack?
Product taste
- Show me a UI you designed for an AI feature. Why did you make those choices?
- Describe a time you talked a client out of building an AI feature.
- How do you measure success beyond "shipped"?
Culture
- Who from your team will I talk to daily?
- How do you handle disagreements about scope?
- What's your escalation path when something breaks in production?
Scoring
Score each 0–3. Any vendor under 60/81 is a pass. Anyone dodging 3+ questions is out. Real teams answer specifically; wrappers answer with slogans.
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FAQ
Frequently asked questions
How long should an AI RFP process take?+
2–4 weeks for a mid-size project. Anything longer and you'll lose good vendors to faster clients.
Should I share our data with vendors during the RFP?+
Only under NDA and only anonymized samples. Reserve real data for the pilot phase.
How many vendors should I invite?+
3–5 is the sweet spot. More than 7 and you can't seriously evaluate each response.
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