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Questions Checklist

Understanding Requirements

Functional

Core user workflows?
What data stored, how long?
Required integrations?
Critical features vs nice-to-haves?

Non-functional

How many users (now and in 1-2 years)?
Acceptable latency? (p99 < 500ms? < 100ms?)
Availability target? (99.9%? 99.99%?)
Consistency requirement? (strong? eventual?)
Data retention policy?
Compliance requirements? (GDPR, HIPAA, SOC2?)

Constraints

Technical

Existing systems to integrate with?
Technologies already in use?
Current team expertise?
Deployment environment? (cloud, on-prem, hybrid?)

Business

Budget for infrastructure?
Timeline for delivery?
Acceptable technical debt?
Long-term vision (1-2 years)?

Organizational

How many engineers will work on this?
Team structure and communication patterns?
Deployment frequency? (multiple/day, weekly, monthly?)
On-call and support model?

Technology Selection

For each choice ask:

Why this over alternatives? (specific reasons, not "popular")
What production experience exists? (internal or external)
Operational complexity?
Vendor lock-in risk?
Community support and longevity?
Total cost of ownership?
Can we hire for this technology?

Risk Assessment

For each decision:

Blast radius if this fails?
Rollback strategy?
How will we detect problems?
Contingency plan?
What assumptions are we making?
Cost of being wrong?