That said, there are valid reasons to delay a migration — but they rarely come from tech debt or team gaps. The real red flags are business-timing related:
Signs You’re Overdue
In most cases, companies don’t migrate too early — they migrate too late. If you're seeing the following, you're probably already paying the price of delay:
The Cost of Waiting
We’ve seen what happens when companies delay the decision too long:
Good Timing for Migration
The best migrations happen during windows of strategic clarity — ideally when the team can breathe a little. Good moments include:
How to Scope It Right
Once you commit, the trick is to scope smart. We never recommend migrating everything at once. Instead:
What Readiness Really Means
Migration readiness isn't about your CI/CD maturity. It’s not about having perfect diagrams or hiring three platform engineers first. Readiness means:
When Is the Right Time to Migrate to AWS? A CTO’s Guide