Cloud Solutions
Cloud migration checklist for small businesses
By Damir Grubisa, CEO, Group 4 Networks
What this checklist is for
Moving email, files, or a line of business application to the cloud is an operating change, not only an IT task. This checklist is a general guide for small businesses. It does not describe a specific client project, and it does not promise savings or a timeline. Use it to prepare questions before you sign a statement of work.
Group 4 Networks has published managed IT guides since 2008. The same questions apply whether you stay with your current provider or you ask a new one to run the move. If you want the broader service definition first, read what managed IT services are.
Decide what "done" means
Write down the outcome in business language. Examples include "staff can open mail and files from the office and from home" or "the accounting application stays available during business hours." Avoid a goal that is only the name of a product.
Name the owner on your side. Someone has to approve the cutover window, tell staff what will change, and decide which old system is turned off. A provider can recommend a sequence. The business still owns the decision.
Inventory what you already have
List mailboxes, shared mailboxes, file shares, desktop applications, line of business systems, printers, and any website or database a vendor hosts for you. Note who uses each one and whether it has to stay available during the workday.
Record where identities live today. If people sign in with separate passwords for mail, files, and the accounting system, the migration plan should say whether those sign-ins will be joined or left alone. Forgotten accounts and old administrator passwords are a common reason a cutover slips.
Ask the provider which items are in scope and which are not. A mailbox move and a full application rebuild are different projects. The checklist in what is included in managed IT services is a useful companion when you separate monthly service from one-time project work.
Protect data before you move it
Take a backup you have actually tested, and keep it until the new environment has been used for a normal work cycle. A copy that has never been restored is not a recovery plan. Confirm who can restore it, how long a restore is expected to take, and where the copy is stored.
Agree what happens to the old servers or file shares after cutover. Some firms keep them read-only for a set period. Write that period down so disks are not wiped on the first quiet Friday.
Plan access, mail, and files
For mail, confirm mailbox size limits, shared calendars, conference room resources, and any scanner or application that sends mail. For files, confirm folder permissions, not only the copy of the data. A file that arrives without the right access is not usable.
Multi-factor authentication should be part of the plan, not a follow-up that never happens. New cloud accounts are a common target in the first weeks after a move, when staff are still learning the sign-in page.
Write a short staff note before cutover day. It should say what will look different, who to call, and what to do if a file is missing. Surprise is what turns a routine move into a Monday outage.
Rehearse the cutover
Pick a window when the business can pause the system you are moving. A rehearsal with a small group finds permission issues and printer paths that a paper plan will miss. The rehearsal does not have to be elaborate. It does have to use a real mailbox or a real shared folder.
On cutover day, keep a list of what was moved, what was deferred, and who confirmed that the important workflow still works. Defer items in writing. Verbal leftovers disappear.
After the move
Check backups in the new environment, not only the backup you took before the move. Confirm mobile devices, home computers, and the office network all reach the new service. Watch the help desk queue for the first two weeks. Repeated tickets usually point at one permission, one printer, or one sign-in step that the plan missed.
Then decide what stays as monthly managed IT and what was only project work. Flat monthly pricing should describe monitoring, patching, support, and the cloud services you actually use. Project work such as a mailbox migration should be scoped separately so the monthly fee is not a surprise later. The guide to how flat rates work lists the questions worth asking.
Questions to ask before you start
- Which systems are in this phase, and which are explicitly out of scope?
- Who approves the cutover window, and how will staff be told?
- Where is the tested backup, and who can restore it?
- How will sign-in and multi-factor authentication work on day one?
- What is included in the monthly service after the project ends?
Related reading: why small businesses use managed IT.