AI Vendor Evaluation: My 30-Minute Framework

You're evaluating an AI vendor. They've given you a demo. The product looks good. Now what?

Most firms don't have a systematic way to evaluate vendors, so they end up choosing based on demo quality or what the vendor's sales team emphasized.

Here's a 30-minute framework that cuts through the noise and identifies the critical questions.

The Six Questions

1. Security and Compliance (5 minutes)

Ask directly:

• "Do you have SOC 2 Type II compliance?" (If they say "no" or "we're working on it," move on.)
• "Can you provide a Business Associate Agreement if we process healthcare data?"
• "How is our data stored? Where are your servers?"
• "How do you handle data encryption in transit and at rest?"

If they can't confidently answer these, don't use them with sensitive data. Period.

2. Integration Complexity (5 minutes)

Ask:

• "What systems does your product integrate with? Specifically, does it integrate with [your CRM/document system/email platform]?"
• "If integration isn't available, what's your timeline?"
• "How much custom development would our team need to do?"

If integrating with your systems requires significant custom work, the cost and timeline will be much higher than the vendor tells you.

3. Latency and Performance (5 minutes)

Ask to run a test:

• "Can I run a test with my actual data to see how fast this processes?"
• "What are your average response times?"
• "What happens during peak usage times?"

If the demo feels fast but you're concerned about production performance, ask for a production-size test.

4. Cost and Lock-In (5 minutes)

Ask directly:

• "What's the actual total cost of ownership? Include licensing, implementation, training, and support."
• "How much of our data do you need to function? Can we use it without uploading our proprietary data?"
• "What happens to our data if we cancel? Can we export it?"

Lock-in is real. Vendors are happy to take your data but make it hard to leave. Understand the exit cost before you commit.

5. Vendor Stability and Support (5 minutes)

Ask:

• "How long has your company been in business?"
• "What's your revenue/funding situation?" (Are they venture-backed? If so, what happens when VCs want returns?)
• "What's your support model? Do we get a dedicated person or a help desk?"
• "What's your uptime SLA?"

You don't want to bet your operations on a vendor that might not exist in two years or might pivot to a different market.

6. Actual Customers Using It for Your Use Case (5 minutes)

Ask:

• "Who are your professional services firm customers?"
• "Can you connect me with someone using this for [your specific use case]?"
• "What would they say are the biggest surprises or challenges?"

References matter. Not vendor references (of course the vendor will give you happy customers), but customers in your industry, doing your work, who can speak candidly.

Red Flags

If you hear any of these, be very cautious:

• "We don't have SOC 2, but we're very secure" — They're not serious about enterprise customers
• "Integration takes about 8 weeks once you sign a contract" — They're hiding complexity
• "We can't share references" — There's something they don't want you to know
• "Our pricing is customized" — That means different people pay different amounts; you'll negotiate poorly
• "You'd need our professional services team to implement" — That's expensive add-on cost
• "Our data training model will improve your results" — They're planning to use your data

Green Flags

These suggest a vendor worth taking seriously:

• They have SOC 2 and can provide a BAA
• They integrate with major platforms; custom integration is optional, not required
• They provide multiple customer references who will talk to you candidly
• They have clear pricing (not "call for custom quote")
• They're transparent about limitations. No vendor is perfect; ones that admit weakness are more trustworthy
• They don't require you to upload proprietary data to use the product

Making the Decision

You don't need to spend weeks evaluating vendors. Thirty minutes of good questions gives you far more signal than hours of demos.

If the vendor can answer these six questions directly and confidently, and they pass the red flag test, they're worth piloting. If they can't or won't answer, move on.

Good vendors welcome good questions. Ones that are vague or defensive are sending you a signal.