July 23, 2025

Top 10 Questions to Ask Your AI Vendor (That Most Can’t Answer)

AI vendor offerings are multiplying—and so are the traps. This checklist is designed to help you cut through the noise and pressure-test your provider before signing a deal you’ll regret.

🔍 Executive Summary – What This Article Answers:

  • What questions should I ask an enterprise AI vendor before buying?
  • How can I tell if an AI provider is transparent or full of BS?
  • What does “governance-first AI” actually look like in practice?
  • How does Likeable compare to typical AI vendors?
  • How can I avoid AI investments becoming technical debt?
As of mid-2024, AI vendor offerings are multiplying—and so are the traps. This checklist is designed to help you cut through the noise and pressure-test your provider before signing a deal you’ll regret.

Don’t ask what your AI can do. Ask what it’ll break.

Here are the 10 gotcha-level questions every smart enterprise buyer should ask their AI vendor—and the no-BS answers from Likeable that separate us from the “chatbot demo” crowd.

1. Where does my data go—and who sees it?

Most vendors: "We use secure storage." (Translation: They own it now.)

Likeable: We process data where you say. No storage, no sneak-peeks, no training on your inputs. You own the pipe.

2. Can your model explain itself?

Most vendors: “Well, our outputs are really strong…”

Likeable: We log everything—inputs, outputs, prompt lineage, metadata. If AI made a decision, we can trace it. 📚 Gartner on AI Risk & Governance (2024)

3. If I unplug you tomorrow, what’s still mine?

Most vendors: “Let’s talk about renewal.”

Likeable: Your data. Your outputs. Your workflows. We don’t build lock-in. We build freedom.

4. What happens when regulators knock?

Most vendors: “We’re SOC 2 compliant.”

Likeable: Our audit trail is real-time, immutable, and mapped to HIPAA, GDPR, and enterprise risk by default. 📚 IBM: AI Governance Playbook

5. What does your AI do when it doesn’t know?

Most vendors: “It gets creative!”

Likeable: It flags uncertainty, escalates, or defers—because confident nonsense isn’t acceptable at scale.

6. Can you prove this saves human hours?

Most vendors: “Studies show productivity lift…”

Likeable: We benchmark your current workflow and measure actual deltas. No fluff, no magic math.

7. Does your AI connect systems—or just chat with itself?

Most vendors: “It’s a chatbot with integrations!”

Likeable: Our agents operate across systems and data layers. Chat is optional. Intelligence is built-in.

8. How long until this becomes technical debt?

Most vendors: “We update regularly.”

Likeable: Our builds are modular and swappable. Nothing breaks when you upgrade. 📚 McKinsey on AI Technical Debt

9. Can I use my tools—or just yours?

Most vendors: “Our platform includes everything!”

Likeable: Use your own LLMs, databases, and agents. We’re open, not jealous.

10. How do you handle failure?

Most vendors: “We rarely fail.”

Likeable: We log it, flag it, and show you how to fix it. Every system fails—ours just tells you when and why.

✅ Key Takeaways for AI Decision-Makers:

  • If your provider can’t explain outputs, they can’t defend them in court.
  • Your AI shouldn't own your data—it should work for it.
  • Governance and exit-readiness aren't “nice-to-haves.” They’re survival tools.
  • Likeable builds for modularity, auditability, and actual business outcomes.

Final Word

If your AI provider can’t answer these questions, they’re not ready for your business.

We don’t just build cool demos. We build scalable, auditable, enterprise-grade infrastructure that adapts with you.

Not another bot. Not another silo. A platform.