Application Migration Checklist for CTOs and Product Leaders

Use this checklist before and during application migrations. Print it for steering meetings. Skip items at your own risk.

Discovery

• ☐ Business owner and technical owner named
• ☐ System inventory: apps, jobs, queues, files, third parties
• ☐ Data classification (PII, financial, regulated)
• ☐ Current SLAs / error budgets documented
• ☐ Success metrics and budget approved

Design

• ☐ Target architecture and ADRs recorded
• ☐ Migration pattern chosen (strangler / dual-run / freeze window)
• ☐ Security review (auth, secrets, network, tenancy)
• ☐ Observability plan (logs, metrics, traces, alerts)
• ☐ Rollback criteria and time limit defined

Build & test

• ☐ Automated tests for critical journeys
• ☐ Data migration rehearsal on production-sized sample
• ☐ Load test on new path
• ☐ Chaos/failure drill for dependencies
• ☐ Access control tested for cross-tenant / role bugs

Cutover

• ☐ Communications plan (customers, support, status page)
• ☐ On-call roster and war room
• ☐ Feature flags / traffic switch ready
• ☐ Backup verification completed hours before
• ☐ Go/no-go meeting with written decision

Hypercare (first 1–2 weeks)

• ☐ Elevated monitoring and daily standups
• ☐ Fast path for defect triage
• ☐ Cost dashboards watched daily
• ☐ Lessons learned + backlog for residual debt
• ☐ Decommission plan for old system scheduled

Frequently asked questions

Who should run the go/no-go?

Product owner + engineering lead + ops, with an executive sponsor for high-risk systems. Silence is not consent.