A customer says 'we want an AI assistant over our docs.' What's your first 30 minutes with them?
Think first
Think about: discovery questions, constraints, scale, compliance, success criteria.
Strong answer
Run structured discovery — don't start building. Key questions in the first 30 minutes: (1) What document sources matter most? (policies, procedures, tickets, code?) (2) What's the scale — how many documents, how many users, peak concurrency? (3) What access-control groups exist and how are they managed? (AD, Okta?) (4) What's the acceptable latency and the uptime SLA? (5) What compliance regimes apply? (GDPR, HIPAA, SOC2?) (6) What's the audit requirement? (retention, fields logged) (7) What's the budget envelope — per-query and monthly? (8) What does success look like in 3 months? (deflection rate, CSAT, time saved) (9) Who are the stakeholders and decision-makers? (10) What's the deployment environment? (cloud, on-prem, hybrid) The goal: leave with a constraints register and a clear picture of whether this is a 2-week POC or a 6-month enterprise deployment. Never start building before this conversation.
Weak-answer indicators
- Starts designing architecture immediately
- Doesn't ask about access control
- Skips compliance and audit
- Doesn't establish success criteria
Likely follow-up questions
- How do you push back on unrealistic timelines?
- What's your POC-to-production process?