Our small-to-medium-sized company has about 50 employees, with roughly 30 people affected by the change. We have used the same IMAP mail server for decades, and everyone currently works with Outlook. Because the setup is outdated and the company is growing, we want to move to a modern hosted provider.
I'm deciding between Microsoft 365 and Google Workspace. Employees already use a mix of Excel and Google Sheets, but some tasks genuinely require desktop Excel. Google Workspace seems easier for collaboration and may be simpler to administer, but I'm concerned about retraining people who have used Outlook for years. The biggest technical concern is also migrating decades of email from our existing IMAP server.
For anyone who has handled a similar migration, which platform would you choose and what problems should we plan for?
3 Answers
Don’t treat this as only a mail-hosting decision. Separate the email migration from the office-suite decision and inventory the applications, spreadsheets, scripts, shared drives, archives, and devices that people use today.
Whichever provider you choose, run a pilot with the largest mailboxes and a few representative users. Confirm how the migration tool handles interruptions, duplicates, folders, attachments, and very old messages. Also document where calendars, contacts, rules, and local archives live, since those often cause more complaints than the mail itself.
For this particular situation, I would lean toward Microsoft 365 because it preserves Outlook and desktop Excel while still providing hosted email, cloud storage, sharing, and collaboration. Google Workspace can be excellent, but its advantages are more valuable when the organization is ready to change its working habits rather than simply replace an aging IMAP server.
Microsoft 365 seems like the practical choice here. Your users already know Outlook, and some of your work depends on Excel, so you avoid a large retraining effort and keep the applications that people already rely on.
You also don’t have to give everyone the exact same license. Users who only need web applications can use Business Basic, while people who need the full desktop versions of Excel and Office can use Business Standard. You can upgrade only specific users later if they need device management or enhanced security features.
The main thing to investigate before choosing a cutover date is the mail history. Check mailbox sizes, local PST files, shared folders, and any archived mail first. An IMAP migration generally moves email, but not necessarily calendars, contacts, client-side rules, or other Outlook settings. Plan separately for those items.
Google Workspace is worth considering if the company is willing to become browser-first. Its collaboration tools and administration can be simpler, and users can still access Google-hosted mail through Outlook in some setups. However, that does not remove the learning curve if people are expected to move from familiar Outlook workflows to Gmail, Sheets, and Google Drive.
Microsoft 365 is usually the smoother transition when employees already use Outlook, Windows, and Excel. Google Workspace makes more sense when most work is already cloud-based, collaboration is the priority, and the organization is prepared to standardize on browser-based tools rather than preserve desktop Office workflows.
The deciding question is whether the Excel requirement is truly occasional or business-critical. If important workbooks use advanced formulas, macros, add-ins, or complicated formatting, test those files before assuming they will work in Sheets.
A staged migration would help a lot: pre-copy the existing mail, test with the largest and messiest mailboxes, then perform a final synchronization when you change the mail routing. That exposes problems before the whole company is moved.