Is Your Organisation Ready to Leave Google Workspace? A 40-Point Readiness Checklist
Leaving Google Workspace is not just about finding alternative tools. It requires mapping identity dependencies, inventorying automations, assessing data portability, and planning for institutional change. A structured checklist to find out if you are ready.
Organisations considering a move away from Google Workspace tend to fall into two camps. The first assumes it is simple: export your email, copy your files, pick a new calendar. The second assumes it is impossible and does not start.
Neither is correct. Whether you are ready to leave Google Workspace depends on specific, measurable factors: how deeply your identity layer is embedded, how many Apps Scripts nobody documented, how much metadata you can afford to lose, and whether your team has the capacity to absorb the change.
This checklist covers 40 specific readiness factors across eight categories. For each one, you assess whether it is ready (green), partially ready (amber), or not ready (red). The result tells you whether you can migrate now, what you need to address first, and where the real blockers sit.
How to Use This Checklist
Work through each item with your IT lead and at least one representative from operations. For items you cannot answer, mark them red. Not knowing is the same as not being ready.
Count your results: Green items are things you can proceed with. Amber items need work but are not blockers. Red items must be resolved before migration.
Category 1: Identity and Access (5 items)
| # | Readiness Factor | Status |
|---|---|---|
| 1 | You have a complete list of every application connected to Google SSO (SAML and OAuth). | 🟢 🟡 🔴 |
| 2 | You know which applications support alternative identity providers (Keycloak, Authentik, SAML/OIDC-compatible). | 🟢 🟡 🔴 |
| 3 | You have identified applications that only support “Sign in with Google” and have no alternative login method. | 🟢 🟡 🔴 |
| 4 | You have inventoried all OAuth token grants (third-party apps with access to Google data) via the Admin Console. | 🟢 🟡 🔴 |
| 5 | You have a plan for MFA migration (moving from Google prompts/Authenticator to a provider-independent method like hardware keys or a separate TOTP app). | 🟢 🟡 🔴 |
Why this matters: Identity is the foundation. If you cannot disconnect your applications from Google SSO without locking people out, you cannot migrate anything else safely. Complete this category first.
Category 2: Email (6 items)
| # | Readiness Factor | Status |
|---|---|---|
| 6 | You know how many mailboxes exist (active users, shared mailboxes, service accounts). | 🟢 🟡 🔴 |
| 7 | You have inventoried all Google Groups (distribution lists, shared inboxes, access control groups). | 🟢 🟡 🔴 |
| 8 | You have identified all send-as aliases and domain aliases configured in Gmail. | 🟢 🟡 🔴 |
| 9 | You have documented mail routing rules, content compliance policies, and attachment restrictions in the Admin Console. | 🟢 🟡 🔴 |
| 10 | You have tested an email export (Google Takeout or IMAP migration tool) for at least one mailbox and verified the result. | 🟢 🟡 🔴 |
| 11 | You have chosen a target email provider and confirmed it supports your required features (custom domain, aliases, shared mailboxes, CalDAV/CardDAV). | 🟢 🟡 🔴 |
Why this matters: Email migration is technically straightforward but operationally complex. The complications sit in groups, aliases, and routing rules, not in the messages themselves.
Category 3: Files and Documents (7 items)
| # | Readiness Factor | Status |
|---|---|---|
| 12 | You know the total volume of data in Google Drive (personal drives and shared drives combined). | 🟢 🟡 🔴 |
| 13 | You have identified how many files are native Google format (Docs, Sheets, Slides) versus uploaded files (.docx, .pdf, .xlsx). | 🟢 🟡 🔴 |
| 14 | You accept that exporting Google Docs to .docx will lose comments, suggestions, and version history. | 🟢 🟡 🔴 |
| 15 | You have identified documents with cross-document links (Google Doc linking to another Google Doc) that will break on export. | 🟢 🟡 🔴 |
| 16 | You have mapped the permission structure of your shared drives (who has access to what, at what level). | 🟢 🟡 🔴 |
| 17 | You have tested a bulk file export (Google Takeout or Rclone) and verified file integrity. | 🟢 🟡 🔴 |
| 18 | You have chosen a target file storage platform and confirmed it meets your needs for sharing, permissions, and collaborative editing. | 🟢 🟡 🔴 |
Why this matters: Files are the most visible part of the migration. The raw files are portable. The metadata (permissions, comments, versions, links) is not. Knowing what you will lose, and accepting it before you start, prevents surprises mid-migration.
Category 4: Calendar and Scheduling (4 items)
| # | Readiness Factor | Status |
|---|---|---|
| 19 | You have inventoried room resources and booking configurations in Google Calendar. | 🟢 🟡 🔴 |
| 20 | You know which third-party scheduling tools (Calendly, SavvyCal, etc.) pull availability from Google Calendar. | 🟢 🟡 🔴 |
| 21 | You have identified CRM or project management integrations that sync with Google Calendar. | 🟢 🟡 🔴 |
| 22 | Your target email/calendar provider supports standard calendar protocols (CalDAV, iCalendar .ics import). | 🟢 🟡 🔴 |
Category 5: Apps Script and Automations (5 items)
| # | Readiness Factor | Status |
|---|---|---|
| 23 | You have a complete inventory of all active Apps Scripts in your organisation (check Script Dashboard in Admin Console). | 🟢 🟡 🔴 |
| 24 | For each Apps Script, you know what it does, who created it, and which business process depends on it. | 🟢 🟡 🔴 |
| 25 | You have identified which Apps Scripts can be replaced by features in the target platform and which must be rebuilt from scratch. | 🟢 🟡 🔴 |
| 26 | You have identified Google Sheets with custom functions written in Apps Script that will break on export to Excel or another format. | 🟢 🟡 🔴 |
| 27 | You have estimated the development effort required to rebuild critical automations on the target platform (n8n, Activepieces, or custom scripts). | 🟢 🟡 🔴 |
Why this matters: Apps Script is the single most common source of migration surprises. Organisations consistently underestimate how many scripts exist and how many processes depend on them. If you cannot answer items 23 and 24, you are not ready to set a migration timeline.
Category 6: Communication (4 items)
| # | Readiness Factor | Status |
|---|---|---|
| 28 | You have decided whether Google Chat/Spaces history needs to be preserved or whether a clean start is acceptable. | 🟢 🟡 🔴 |
| 29 | You have identified all Google Meet integrations (calendar auto-links, third-party recording tools, meeting room hardware). | 🟢 🟡 🔴 |
| 30 | You have chosen a target communication platform and tested it with a pilot group. | 🟢 🟡 🔴 |
| 31 | External stakeholders who join your Google Meet calls have been considered (clients, partners, candidates). | 🟢 🟡 🔴 |
Category 7: Admin Console and Security (5 items)
| # | Readiness Factor | Status |
|---|---|---|
| 32 | You have documented all security settings in the Google Admin Console (2-step verification policies, session controls, allowed apps). | 🟢 🟡 🔴 |
| 33 | You have exported or documented DLP rules configured for Gmail and Drive. | 🟢 🟡 🔴 |
| 34 | You have exported audit logs for the retention period you need (Google retains admin logs for 6 months by default). | 🟢 🟡 🔴 |
| 35 | You have identified all Google Workspace Marketplace apps installed across your organisation. | 🟢 🟡 🔴 |
| 36 | You have a plan for device management migration if you use Google Endpoint Management. | 🟢 🟡 🔴 |
Category 8: Organisational Readiness (4 items)
| # | Readiness Factor | Status |
|---|---|---|
| 37 | Leadership has approved a migration timeline and budget (including productivity loss during transition). | 🟢 🟡 🔴 |
| 38 | You have identified a migration lead with dedicated time (not someone doing this on top of their regular job). | 🟢 🟡 🔴 |
| 39 | You have a training plan for the new tools (not a one-hour webinar, but hands-on sessions with follow-up support). | 🟢 🟡 🔴 |
| 40 | You have a communication plan for the transition: what changes, when, what employees need to do, and where to get help. | 🟢 🟡 🔴 |
Why this matters: Technical readiness without organisational readiness leads to failed migrations. If leadership has not allocated budget and time, the migration will stall at the first obstacle.
Scoring Your Readiness
Count your responses:
| Colour | Count | Interpretation |
|---|---|---|
| 🟢 Green | ___ / 40 | Ready to proceed |
| 🟡 Amber | ___ / 40 | Needs attention before migration |
| 🔴 Red | ___ / 40 | Blocker: must resolve first |
30+ green, fewer than 3 red: You are in a strong position to begin migration planning. The remaining amber and red items are manageable and can be addressed in the early phases.
20 to 29 green, 3 to 8 red: You have done significant preparation but still have blockers. Focus on resolving the red items, particularly in Categories 1 (Identity) and 5 (Apps Script), before committing to a timeline.
Fewer than 20 green, 8+ red: You are not ready for migration. Start with a dependency audit to map what you have, then use the results to work through this checklist systematically.
The Most Common Blockers
Across organisations we work with, three items consistently show up as red:
Item 23: Apps Script inventory. Almost nobody has one. Building it takes a few hours with the right admin access, and the results are always surprising.
Item 16: Shared drive permissions. Google Drive permissions accumulate over years. Nobody maintains a map. The thought of recreating them in another system is what stops many migrations from starting.
Item 5: MFA migration plan. Organisations that use Google prompts for MFA have entangled their second factor with their primary vendor. Moving to FIDO2 hardware keys or a standalone TOTP app before migration makes everything else simpler.
Start with those three. If you can turn them from red to amber, you have removed the most common reasons migrations stall.
Sovereign Shift assesses all 40 readiness factors as part of our Google Workspace dependency audit and delivers a migration plan tailored to your specific gaps. See pricing and scope →