Cloud Migration Best Practices: Lessons from 100+ Enterprise Migrations

Practical insights and strategies for successful cloud migration, based on real-world experience with enterprise clients.

M
Marcus Chen Author
10 min read
Cloud Migration Best Practices: Lessons from 100+ Enterprise Migrations

After helping over 100 enterprises migrate to the cloud, we’ve distilled our learnings into actionable best practices that can help you avoid common pitfalls and accelerate your journey.

The 6 Rs of Cloud Migration

Every workload falls into one of these categories:

  1. Rehost (Lift and Shift): Move as-is to the cloud
  2. Replatform: Minor optimizations during migration
  3. Repurchase: Move to a SaaS solution
  4. Refactor: Rebuild for cloud-native architecture
  5. Retain: Keep on-premises (for now)
  6. Retire: Decommission entirely

Pre-Migration Assessment

Before you move anything, conduct a thorough assessment:

Application Discovery

  • Inventory all applications and dependencies
  • Map network connections
  • Document integration points

Cost Analysis

  • Calculate current total cost of ownership
  • Project cloud costs (including hidden costs)
  • Identify optimization opportunities

Risk Assessment

  • Security and compliance requirements
  • Data sensitivity classification
  • Business continuity implications

Migration Execution

Phase 1: Foundation

Set up your cloud foundation:

  • Landing zone architecture
  • Identity and access management
  • Network connectivity (VPN, Direct Connect)
  • Security baseline

Phase 2: Pilot

Start with low-risk workloads:

  • Development environments
  • Non-critical applications
  • Test data sets

Phase 3: Migration Waves

Group applications into migration waves:

  • Wave 1: Low complexity, high value
  • Wave 2: Medium complexity
  • Wave 3: High complexity, mission-critical

Phase 4: Optimization

Post-migration optimization:

  • Right-sizing instances
  • Reserved instances planning
  • Auto-scaling implementation

Common Pitfalls to Avoid

  1. Underestimating complexity: Legacy applications often have hidden dependencies
  2. Ignoring security: Cloud security is different from on-premises
  3. Skipping testing: Thorough testing prevents post-migration issues
  4. Forgetting training: Your team needs cloud skills

Measuring Success

Track these metrics throughout your migration:

  • Migration velocity (workloads per month)
  • Cost variance (projected vs. actual)
  • Performance metrics (latency, uptime)
  • Security incidents
  • User satisfaction

Conclusion

Cloud migration is a complex undertaking, but with proper planning and execution, the benefits far outweigh the challenges. Focus on building a solid foundation, start small, and iterate based on learnings.

Need help with your cloud migration? Get in touch with our cloud experts.