By STS Consulting Group | Reading time: 8 minutes
'We'll be fully migrated to the cloud in six months.' Famous last words. Six months later, you're 40% done, over budget, and the team is exhausted.
Cloud migration is harder than vendors suggest and harder than optimistic project plans assume. Here's what actually happens—and how to plan realistically.
Why Migrations Take Longer Than Expected
Most migration timelines fail for predictable reasons:
Discovery surprises: You think you know what you have. You don't. That database server in the corner? It turns out three critical applications depend on it in ways nobody documented.
Interdependencies: Applications don't exist in isolation. They connect to other applications, databases, file shares, and external services. Migrating one piece often requires migrating or modifying others.
Business constraints: You can't migrate the ERP system during quarter close. You can't touch the e-commerce platform during the holiday rush. These constraints compress your actual working windows.
Skills gaps: Your team knows your current environment. Cloud is different. Learning curves are real, and mistakes during learning are expensive.
Day job interference: Migration is rarely anyone's only responsibility. The same people running current operations are supposed to build the new environment. Something gives.
Realistic Timeline Expectations
Every migration is different, but here's a rough framework based on our experience:
Assessment and Planning: 1-3 Months
Inventory everything. Document dependencies. Assess each workload for cloud readiness. Decide what to migrate first, what to modernize, and what to leave alone. This phase is often rushed—don't let it be. Good planning prevents expensive mistakes.
Foundation Building: 1-2 Months
Set up your cloud environment properly: networking, security, identity, monitoring, governance. Cutting corners here creates technical debt that haunts you forever. This is also when you build skills—training, pilots, proof of concepts.
Migration Waves: 3-12+ Months
Migrate in waves, starting with lower-risk workloads. Learn from each wave. Improve your process. Gradually tackle more complex and critical systems. The timeline depends entirely on your scope—a dozen servers is different from hundreds.
Optimization: Ongoing
Migration isn't 'done' when workloads move. You'll spend months optimizing costs, improving performance, and taking advantage of cloud-native capabilities you couldn't use on day one.
The Migration Strategy Decision
For each workload, you need to decide how to migrate it. The options range from quick-and-simple to slow-and-transformative:
Rehost (lift and shift): Move it as-is to cloud infrastructure. Fastest, but you don't get cloud benefits beyond infrastructure flexibility.
Replatform (lift and reshape): Make minimal changes to take advantage of cloud services—like moving to a managed database instead of running your own.
Refactor (re-architect): Significantly modify the application to be cloud-native. Most benefit, most effort, most risk.
Replace: Retire the existing application and adopt a SaaS alternative.
Retire: Turn it off. Migrations are a great time to decommission things nobody uses anymore.
Most organizations use a mix of strategies. The key is making conscious choices, not defaulting to lift-and-shift for everything because it's easier.
Critical Success Factors
Executive sponsorship: Migration requires sustained attention and resources. Without executive support, it loses priority to urgent day-to-day issues.
Dedicated resources: People can't migrate infrastructure while fully handling their normal jobs. Either dedicate time or bring in help.
Business involvement: IT can't decide application priorities and acceptable downtime windows in isolation. Business stakeholders must be engaged.
Rollback plans: Things go wrong. Have a plan for reverting when they do. Test the rollback before you need it.
Celebration of progress: Migrations are marathons. Recognize milestones. Keep morale up. Burned-out teams make mistakes.
How We Help
Our Cloud & Infrastructure Modernization practice has guided dozens of growing companies through cloud migration. We bring experience that helps you avoid common pitfalls, realistic planning that accounts for complexity, hands-on implementation support alongside your team, and knowledge transfer so your team can operate and optimize after migration.
We don't just migrate your workloads—we help you build the foundation for cloud success.
Planning a cloud migration? Schedule a free consultation to discuss your goals and challenges.