1. Hidden Drive sprawl. Personal My Drive folders often hold business-critical content that nobody has catalogued, and orphaned files belonging to departed staff are common. Discovery reports data volume, ownership and orphan status per user so nothing is stranded when Google licences are cancelled.
2. Google-native file conversion. Docs, Sheets and Slides do not move as-is. Complex Sheets with Apps Script, macros or heavy formula logic are identified during discovery and converted, rebuilt or intentionally left in place with a documented decision — never discovered as broken after cutover.
3. External sharing breakage. Client and supplier links into shared drives will break unless they are inventoried and reissued as Microsoft 365 sharing links. We produce that inventory before cutover and coordinate reissue with the owning teams.
4. Third-party app dependencies. Applications authenticating via Google SSO, plus scanners, CRMs and line-of-business tools sending mail through Google SMTP relay, all need re-pointing to Entra ID and Exchange Online. Missing one is the classic cause of a silent post-cutover outage.
5. Change fatigue. The technical migration is usually easier than the behavioural one. Role-based enablement, quick-reference guides for the common Gmail to Outlook questions, and floorwalker support in cutover week keep adoption — and the service desk queue — under control.