Is Your Business Ready for the Cloud? A 10-Point Checklist
Moving to the cloud can improve reliability and reduce costs. But it is not the right move for every business at every stage, and a poorly planned migration creates more problems than it solves. Before you migrate anything, work through these ten questions.
- 1
Do you know exactly what you are running today? Before you migrate, audit your current setup. What servers are you running? What software depends on them? What would break if a server went down? You cannot plan a migration without a clear picture of your starting point.
- 2
Is your internet connection reliable? Cloud-based work depends on consistent internet access. If your office connection drops frequently or slows down at peak times, moving to the cloud will expose that problem, not fix it. Address your connection first.
- 3
Are you already on Microsoft 365 or Google Workspace? Most small businesses are partway to the cloud already. If you are paying for 365 or Google Workspace, you have email, file storage, and collaboration tools ready to use. The question is whether your team is actually using them.
- 4
Is your data backed up right now, before migration? Cloud storage is not the same as cloud backup. OneDrive and Google Drive sync in real time, which means they can sync a ransomware infection or accidental deletion too. Have a proper backup in place before you move anything.
- 5
Do you handle data with compliance requirements? Healthcare records, financial data, and legal documents come with regulatory obligations. Moving that data to the cloud requires specific configuration and documentation. A default setup is not sufficient.
- 6
What happens if the cloud service goes down? Every cloud provider has outages. How would your team work if Microsoft 365 was unavailable for four hours? Think through your continuity plan before you migrate, not after.
- 7
Is your team ready to change how they work? Technical migration is the straightforward part. Getting staff to actually use new tools consistently is harder. Budget time for training and expect an adjustment period.
- 8
Do you understand your licensing costs? Cloud licensing is subscription-based and can add up fast. Businesses migrating to Azure or 365 without reviewing their license structure often end up overpaying within the first quarter.
- 9
Who will manage the environment after migration? Cloud infrastructure still needs active management. Security settings drift, old user accounts accumulate, and permissions spread over time. Someone needs to own ongoing management.
- 10
Do you have a rollback plan? Know what you will do if the migration goes sideways before you start, not after. A migration without a rollback plan is a migration with unnecessary risk.
If you answered 'not sure' to more than three of these, that is worth a conversation before you sign any contracts. We do free cloud readiness reviews for businesses in the Chicago area. We will go through your setup and tell you honestly whether you are ready and what to do first.
ITM Consulting
Questions about your IT setup?
We work with small businesses and accounting firms across the Chicago area. Schedule a free 30-minute consultation and we will tell you honestly what we see.