Most failed cloud migrations don't fail because the cloud provider had a problem. They fail because the move was treated as a single weekend event instead of a staged process. Here's the sequence we use with clients to keep the business running throughout.
Start with an inventory, not a shopping list
Before picking a provider, document what you actually run: applications, dependencies between them, data volumes, and which systems are genuinely business-critical versus merely convenient. This inventory — not a vendor's pricing page — should drive every decision that follows.
Group workloads by migration strategy
Not everything moves the same way. Some applications can be "lifted and shifted" as-is; others need re-architecting to take advantage of cloud pricing and scaling; a few legacy systems may be better left on-premises entirely, at least for now. Forcing every workload through the same strategy is where budgets and timelines usually break down.
Migrate in order of blast radius, not order of ease
It's tempting to start with the easiest system to build confidence. We recommend the opposite for the first real migration: pick a moderate-risk, non-critical workload first, so mistakes are cheap to make and the lessons apply to the harder systems that follow.
Run parallel, don't cut over
For anything customer-facing, run the old and new systems side by side, with data syncing between them, before switching traffic over. This turns a risky one-time cutover into a reversible, low-drama switch — and gives you a rollback path if something's wrong.
Plan the network path before the data path
Cloud migrations often move slower than expected because nobody tested how staff actually connect to the new environment — VPN capacity, latency to the region you chose, and firewall rules all need attention before go-live, not after.
Set a cost ceiling before you start, not after the first invoice
Cloud costs scale with usage, and usage has a way of growing quietly. Set budget alerts before migrating a single workload, and review actual spend against the estimate at 30 and 90 days — cost overruns are far easier to catch early than to unwind later.
Decommission deliberately
The final, often-skipped step: once a workload has run successfully in the cloud for a defined period, formally decommission the old infrastructure. Keeping it "just in case" indefinitely means paying for two environments and never fully realizing the migration's benefits.
Done this way, a cloud migration is a series of small, reversible steps rather than one high-stakes weekend. If you're weighing a move and want a second opinion on sequencing, talk to our team — we're happy to look at your setup before you commit to a plan.