For a small business, the Microsoft 365 versus Google Workspace decision is less about which suite is "better" and more about which one fits how your team already works, what you can migrate without pain, and which security posture you can actually administer. Both are mature, reliable, and capable of running a whole company. The differences that matter at the 15-to-200-employee scale are practical, not ideological.
Fit: where your team already lives
Google Workspace is built browser-first. If your staff lives in Chrome, collaborates in real time on shared documents, and rarely touches heavy desktop formatting, Workspace tends to feel native and low-friction. Its real-time co-editing has been the benchmark for years, and admin is comparatively simple.
Microsoft 365 wins when the desktop apps are non-negotiable. Finance teams with complex Excel models, anyone exchanging heavily formatted Word documents with outside parties, and organizations standardized on Outlook will find that the web versions of Google's apps do not fully replace what they rely on. M365 also bundles Teams, which for many SMBs becomes the chat-and-meetings backbone, and its desktop Office apps still handle edge-case formatting more faithfully than imported equivalents.
Migration: the part that actually hurts
The suite is easy; the move is not. Migrating mail, calendars, contacts, and especially shared files carries the real cost and risk. A few things consistently cause pain:
Email migration with intact folder structures, calendar invites, and shared mailboxes, without a gap in delivery during cutover.
File migration where folder permissions and sharing links have to be re-mapped, since the two platforms model sharing differently.
User retraining, which is a soft cost people forget; productivity dips for a couple of weeks regardless of which direction you move.
If you are starting fresh, pick the one that fits and move on. If you are switching, budget for the migration as a project with a defined cutover, not a weekend toggle.
Security: what you can administer matters more than the feature list
Both platforms offer strong security at their business tiers: multi-factor authentication, conditional access, device management, data-loss prevention, and audit logging. The deciding factor for an SMB is usually not which checklist is longer but whether someone on your side is actually configuring and monitoring those controls. A perfectly capable security suite left at its defaults is a half-locked door. Enforced MFA, sensible sharing limits, and someone watching the admin alerts beat any feature comparison.
The suite rarely fails a small business. The unconfigured suite does.
That administrative gap is where most small companies get stuck, because the owner picked a platform but no one owns the security configuration, the license cleanup, or the offboarding process when someone leaves. This is the work that benefits from outsourced IT support for a small business: not the dramatic projects, but the steady governance that keeps either platform secure and tidy. Choose M365 if you are desktop-Office-heavy and want Teams as your hub; choose Workspace if you are browser-first and value simplicity. Either way, the decision that protects you is committing to administer whichever one you pick.
