Leaving Google Workspace without losing the firm’s working files

A 180-person firm had outgrown a Google-first stack. Clients were on Microsoft; proposals lived in messy shared drives; offboarding was inconsistent. Leadership wanted Microsoft 365 for desktop apps, client collaboration, and tighter identity control, not a lift-and-shift that dumped chaos into OneDrive.

• ~180Users migrated
• 5 weeksPilot to hypercare
• 2 pilotsFinance + operations first
• Day 1Teams-ready landing zones

The situation

Google Workspace had been “good enough” for years. Then the firm started winning larger clients who expected Word/Excel co-authoring, Teams meetings, and a more formal security posture. Internal IT was a lean team. They didn’t want a six-month transformation program, they wanted a clean move with training that stuck.

Shared drives were the real landmine: ownership unclear, folders nested by habit, and several “company-wide” spaces nobody wanted to own after go-live.

What we refused to skip

• Mapping Gmail, Calendar, Drive, and shared drives before any bulk job ran
• Building the target tenant with MFA and licensing by role, not defaults
• Designing where files should live after migration (Teams channels vs SharePoint libraries vs OneDrive)
• A pilot that included people who live in client folders all day, not only IT
• Role-based training the week before each wave, not a single all-hands demo

How the work unfolded

Discovery and file destination design

We sat with practice leads and asked a boring, useful question: “Where should this live six months from now?” Personal working files stayed personal (OneDrive). Client and delivery content landed in owned SharePoint sites and Teams. That decision did more for adoption than any tool feature.

Target tenant baseline

Entra ID, MFA enrollment, and licensing pools were ready before the first pilot. We avoided the classic failure mode: users land in Microsoft 365, then spend two days stuck on authentication and missing licenses.

Pilot waves that reduced fear

Finance and operations went first. They’re picky about calendar fidelity and shared mailboxes, if those groups are calm, the rest of the firm usually follows. We fixed folder permission surprises and Outlook quirks in pilot, then moved the delivery practices in two production waves.

Training that matched real jobs

Sessions were short and role-based: partners on calendar + desktop apps, coordinators on shared mailboxes and Teams channels, consultants on OneDrive vs channel files. People cared less about feature tours and more about “where did my proposal folder go?”

Workload coverage

Results

• Mail, calendar, and Drive content moved across staged waves without a multi-day freeze
• Users landed in Teams-ready collaboration spaces instead of a flat dump of Drive trees
• IT gained centralized MFA, offboarding, and device-aligned controls on day one
• Helpdesk tickets clustered around “where is this file?”, and dropped after the second training pass

The pilot made go-live boring, in a good way. People knew where files lived before we flipped everyone.

- Head of Operations

If you’re considering the same move

Google → Microsoft is as much information architecture as it is migration tooling. If you only copy bits, you’ll recreate the same mess with different icons. Decide destinations, pilot the loudest departments, and train on the three places files can live: OneDrive, SharePoint, and Teams.