Cloud migrations fail not because the cloud is hard, but because the questions that matter most never get asked. By the time the bill arrives — or the cutover weekend goes sideways — the answers are no longer free.
Below is the checklist we run with every prospective migration client before we'll quote a number. None of the questions are technical, but the answers have technical consequences. Bring them to your next vendor conversation and watch how quickly the room sorts itself out.
About the workload itself
- What problem are we actually solving? "We want to be in the cloud" is not a problem. "Our current hardware is end-of-life and replacing it on-prem will cost $180k" is.
- What does this system do, and who uses it? Identify the top three workflows that matter most to the business and trace them end-to-end.
- What's the real performance budget? Get concrete: peak users, peak transactions, acceptable latency, recovery-time objective.
- Where's the data, and how much of it is there? Egress costs and migration windows are functions of size. Don't guess.
About the people
- Who owns this after we're done? If the answer is "we'll figure it out," the project will fail in month four.
- What skills does the receiving team have today? AWS or Azure? Terraform or click-ops? Be honest — the training plan is part of the budget.
- Who's the executive sponsor? Migrations surface ugly tradeoffs. You need someone with authority to pick a side when they do.
About the money
- What's the current run-rate, all-in? Hardware amortization, software licenses, electricity, people. The cloud isn't always cheaper, but you need a fair baseline to compare against.
- What's the budget for the migration itself? Not the steady-state — the one-time cost of moving.
- Who's signing off on cloud costs each month? Reserved instances, savings plans, and right-sizing only happen if someone owns the bill.
About what could go wrong
- What's the rollback plan? "We'll just go back" stops being true the moment the on-prem environment is decommissioned.
- What integrations and dependencies exist? The on-prem fax server that talks to the EHR is the kind of thing that bites at 2am during cutover.
- What does compliance look like? HIPAA, PCI, FedRAMP, state-specific privacy laws — all change the shape of the design.
- What's the cutover window? Weekends? Holidays? Quarter-end? The business answer drives the technical plan, not the other way around.
If you can't answer ten of these fourteen, you're not ready to migrate yet — you're ready to hire someone to help you answer them.
What to do with the answers
Take the completed checklist into your vendor conversations and watch how the proposals change. Vendors who can engage with the questions are the ones worth taking seriously. Vendors who skip past them are the ones who'll surprise you later.
If you'd like a second pair of eyes on a quote you've already received, get in touch — we'll spend an hour reviewing it with you, no commitment.