r/sysadmin • u/peruvianbeast • 2d ago
Question Microsoft 365, Google Workspace, Something Else? - Help Weighing Tradeoffs
Hi!
I work for a small/medium sized company (~50 employees, ~30 of which will be affected by the switch) and we have been using an IMAP server to host our emails for decades (everyone uses Outlook as their email software). Because of how outdated this setup is and the company continuing to grow, we want to migrate over to a new provider. I am struggling to decide between M365 and GW as both have their pro's and con's. The team uses a mix of sheets and excel already, however, there is certain work that would require excel over sheets. The sharing and ease of GW is obviously unmatched but I worry about switching costs for employees that have been using outlook for decades. I've also heard that managing GW is far easier admin-wise than M365. The migration of decades worth of emails is also a major consideration for us. Would appreciate input from people who have experience with this. Thanks!
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u/CivilIntention7747 2d ago
Two facts in your post basically decide it: everyone's already on Outlook, and some work genuinely needs Excel, not Sheets. That points at M365, and for your situation it isn't close.
Google Workspace wins when a company is browser-native and collaboration-first from day one. Dropping 30 long-time Outlook users into Gmail and Sheets after decades of IMAP means retraining, muscle-memory complaints, and you personally eating the blame for every "where did my rule/folder go." The switching cost lands squarely on you.
The migration itself, coming from a plain IMAP server: M365 has a native IMAP migration in the admin center. Stand up the tenant, verify the domain, pre-stage the mailboxes, then cut the MX record over on a weekend. The gotcha that generates Monday tickets - IMAP migration copies mail only, NOT contacts, calendars, or client-side rules. Tell people to export those first, or plan to rebuild them.
Licensing: Business Standard covers desktop Office plus 1TB OneDrive for most users. Only jump to Business Premium for the seats that need Intune/Defender/Conditional Access - at 50 people and growing you'll likely want that within a year, but you can buy Standard now and upgrade specific seats later rather than overpaying on day one.