Why Migrations Fail
84% of organizations struggle to manage cloud spend after migration. The reason is almost always the same: they migrated technology without migrating strategy.
A successful cloud migration isn't about moving servers. It's about moving your business to a better operating model — with lower costs, better security, and more flexibility.
This checklist covers the full process from assessment to optimization.
Phase 1: Assessment (Weeks 1-2)
Before you move anything, understand what you have.
Infrastructure Inventory
- Catalog all servers (physical and virtual) with specs and utilization
- Document all applications and their dependencies
- Map data flows between systems
- Identify database sizes and growth rates
- Record current bandwidth usage and patterns
- Note compliance requirements (PIPEDA, PHIPA, industry-specific)
Business Requirements
- Define uptime requirements per application (99.9%? 99.99%?)
- Identify performance baselines (response times, throughput)
- Document data residency requirements (must data stay in Canada?)
- List integration requirements with third-party services
- Establish budget constraints and timeline expectations
Risk Assessment
- Identify single points of failure in current infrastructure
- Assess data sensitivity and classification
- Evaluate staff readiness and training needs
- Document rollback requirements (can you go back if needed?)
Phase 2: Strategy (Weeks 2-4)
Choose Your Approach
For each workload, decide:
| Strategy | When to Use | Risk Level |
|---|---|---|
| Rehost (lift and shift) | Quick migration, minimal changes needed | Low |
| Replatform | Minor optimizations during migration | Medium |
| Refactor | Application needs redesign for cloud | High |
| Retire | Application is no longer needed | None |
| Retain | Must stay on-premises (compliance, latency) | N/A |
Most businesses use a mix. Start with rehost for quick wins, then optimize later.
Right-Size from Day One
- Match cloud instance sizes to actual utilization (not current hardware specs)
- Plan for auto-scaling where appropriate
- Choose reserved instances for predictable workloads (save 30-60%)
- Set up cost alerts at 50%, 75%, and 90% of budget
Security Architecture
- Design network segmentation (VPCs, subnets)
- Plan identity and access management (SSO, MFA)
- Define encryption strategy (at rest and in transit)
- Establish logging and monitoring requirements
- Document incident response procedures for cloud
Phase 3: Execution (Weeks 4-8)
Pre-Migration
- Set up cloud accounts and billing
- Configure networking (VPN, direct connect if needed)
- Deploy monitoring and alerting tools
- Create test environment that mirrors production
- Migrate and test one non-critical workload first
Migration
- Follow the prioritized migration order (least critical first)
- Validate each migration against performance baselines
- Test all integrations and data flows
- Verify backup and disaster recovery in the cloud
- Run parallel systems during transition period
Post-Migration
- Decommission old infrastructure (after validation period)
- Optimize resource allocation based on actual cloud usage
- Update documentation and runbooks
- Train staff on new processes and tools
- Schedule 30/60/90-day optimization reviews
Phase 4: Optimization (Ongoing)
This is where most businesses drop the ball. Migration isn't a project — it's the start of a new operating model.
Monthly
- Review cloud spend vs. budget
- Right-size underutilized instances
- Check for unused resources (orphaned storage, idle instances)
- Review security alerts and compliance status
Quarterly
- Evaluate new cloud services that could improve operations
- Assess reserved instance coverage
- Review and update disaster recovery testing
- Plan capacity for upcoming growth
The 3 Biggest Mistakes
- Migrating everything at once: Move in phases. Start with low-risk workloads, learn, then tackle the complex ones.
- Ignoring cost optimization: Cloud flexibility is a double-edged sword. Without governance, costs spiral fast.
- Skipping the parallel run: Keep old systems running for 2-4 weeks after migration. The rollback option is worth the cost.
Getting Started
A cloud migration doesn't have to be overwhelming. Start with the assessment phase — just understanding what you have is half the battle.
If the scope feels too large, a managed service provider can handle the technical execution while you focus on business decisions. The key is starting with clear goals and a realistic timeline.