AI Vendor Selection
Questions to Ask Before You Buy
5 min read • Intermediate Level
The Problem: The AI tool market is overwhelming. Most businesses buy tools they do not need or pick vendors who cannot deliver. Ask these questions before signing.
Capability Questions
Can they actually do what you need?
1. What exactly does your AI do?
Get a specific answer. Vague promises = red flag.
2. What happens if the AI makes a mistake?
Look for: human oversight options, error correction, rollback capabilities.
3. How does your AI learn and improve?
Ongoing learning vs static model = big difference in long-term value.
4. Can it integrate with our existing tools?
CRM, email, accounting, scheduling — what APIs do you support?
Security & Privacy Questions
Your data is your asset. Protect it.
1. Where is our data stored?
Location matters for compliance (PIPEDA, GDPR). Ask about data residency.
2. Do you use our data to train your models?
Opt-out should be available. Your data = your data.
3. What security certifications do you have?
SOC 2, ISO 27001, PIPEDA compliance minimum for Canada.
4. What happens if there's a data breach?
Look for: clear liability, notification process, remediation support.
Support & Success Questions
Implementation support = adoption success.
1. What does onboarding look like?
Self-serve vs dedicated CSM. Complex tools need hands-on onboarding.
2. What support channels are available?
Email, chat, phone? 24/7? Response time SLAs?
3. Do you offer training or documentation?
Video tutorials, knowledge base, live training sessions.
4. Who is our point of contact?
Dedicated CSM, account manager, or rotate through support?
Business Viability Questions
You need this vendor around in 2 years.
1. How long have you been in business?
AI space has high churn. Look for 3+ years minimum.
2. How many customers do you have?
Reference customers in your industry = validation.
3. What is your pricing model?
Per user, per usage, flat fee? Hidden costs? Annual vs monthly?
4. What does your roadmap look like?
They should be innovating. AI moves fast — static vendors lose.
Trial & Pilot Questions
Test before you commit. Seriously.
1. Do you offer a free trial?
Minimum 7-14 days. 30 days ideal. No trial = no buy.
2. Can we run a paid pilot first?
3-month pilot with success criteria = lower risk.
3. What does cancellation look like?
Month-to-month ideal. Long contracts = avoid.
4. Can we talk to existing customers?
References = credibility. Refusal to provide = red flag.
🚩 Red Flags — Walk Away If:
✅ Green Flags — Good Signs:
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