Migrate from Google Workspace: Complete Planning Guide

You've decided Google Workspace no longer meets your needs. The hidden costs outweigh the benefits. It's time to migrate.

But how do you actually do it without creating chaos?

This guide provides a practical framework for Workspace migration—from assessment through execution—based on successful migrations across hundreds of organizations.

Phase 1: Assessment and Planning

Inventory What You're Migrating

Before planning migration, understand what exists:

Data inventory:

• Gmail: Email archives, contacts, labels
• Drive: Files, folders, shared drives, ownership
• Calendar: Events, recurring meetings, shared calendars
• Meet: Recordings (if stored)
• Docs/Sheets/Slides: All document types and formats
• Sites: Any Google Sites in use
• Groups: Distribution lists and their members

Usage inventory:

• Active users per product
• Storage consumption per user
• Shared drives and their owners
• External sharing configurations
• Custom integrations and add-ons

Dependency inventory:

• Third-party tools connected to Workspace
• Automation workflows (Zapier, etc.)
• SSO configurations
• Custom domain email routing

Assess Migration Complexity

Score each component:

Higher complexity requires more planning, longer timelines, and potentially professional migration services.

Define Target Architecture

Questions to answer:

• What platform(s) will replace Workspace?
• What functionality maps to what in the new system?
• What changes in workflow are acceptable?
• What gaps will exist and how will they be addressed?

Common migration targets:

• Microsoft 365 (most common enterprise migration)
• Unified platforms like Waymaker Commander
• Best-of-breed combinations (various tools for different functions)
• Hybrid approaches (new platform + some Workspace products retained)

Establish Timeline

Typical timeline components:

Total typical timeline: 3-6 months for organizations with 100-500 users.

Phase 2: Technical Preparation

Email Migration Approach

Options:

Cutover migration: Everyone moves at once

• Best for: Small organizations (< 50 users)
• Advantage: Simple, fast completion
• Risk: Disruption affects everyone simultaneously

Staged migration: Groups move in waves

• Best for: Medium organizations (50-500 users)
• Advantage: Contains risk, allows learning
• Risk: Temporary complexity of split systems

Hybrid migration: Some users move, others remain

• Best for: Complex situations with long transition needs
• Advantage: Flexibility
• Risk: Ongoing complexity and cost

Technical considerations:

• IMAP migration vs. third-party migration tools
• PST intermediate format for some scenarios
• Label/folder structure mapping
• Archive handling decisions

Drive Migration Approach

Complexity factors:

• Shared drive ownership and permissions
• External sharing links that break on migration
• Google-format files needing conversion
• Large file handling

Migration options:

Manual export/import:

• Google Takeout for data export
• User-driven import to new platform
• Simple but relies on user compliance

Third-party migration tools:

• BitTitan, SkyKick, CloudM, etc.
• Automated transfer with permission mapping
• Typical cost: $5-20 per user

Professional services:

• Vendor-provided migration assistance
• Managed migration with support
• Typical cost: $20-100+ per user

Calendar Migration

Considerations:

• Recurring event handling across platforms
• Room and resource calendars
• External calendar invitations
• Integration with scheduling tools

Calendar migration is often easier than email/drive but requires testing recurring events carefully.

Integration Reconnection

For each connected integration:

1. Document current connection configuration
2. Identify equivalent integration on target platform
3. Plan connection timing (before, during, or after migration)
4. Test in pilot phase

Integration complexity can be a significant migration burden—use migration as an opportunity to simplify.

Phase 3: Change Management

Communication Plan

Stakeholder communication:

Key messages:

• Why migration is happening (not just "management decided")
• What will change and what won't
• What support is available
• What users need to do and when

Training Plan

Training content:

• New platform basics (interface, navigation)
• Key workflow differences from Workspace
• Where to get help
• What to do if something doesn't work

Training delivery:

• Live sessions for complex workflows
• Self-paced video/documentation for basics
• Champions/super-users for peer support
• Dedicated support channels during transition

Resistance Management

Common resistance points:

• "Gmail is better than [alternative]"
• "All my files are organized in Drive"
• "I don't have time to learn something new"
• "This will slow me down"

Response approach:

• Acknowledge concerns as valid
• Explain business rationale clearly
• Provide specific support for specific concerns
• Identify super-users to help resistant colleagues

Phase 4: Execution

Pilot Migration

Pilot group selection:

• 10-20 users representing different roles
• Mix of tech-savvy and typical users
• Not all executives (need real feedback, not deference)
• Some critical workflows, not all critical workflows

Pilot objectives:

• Validate migration process
• Identify unexpected issues
• Gather user feedback
• Refine training and support

Pilot success criteria:

• Migration completes without data loss
• Users can perform core functions
• Issue response process works
• Confidence to proceed with larger groups

Wave Execution

Each wave includes:

1. Pre-migration preparation (user notification, data backup)
2. Migration execution (technical process)
3. Verification (data integrity checks)
4. User enablement (access, training, support)
5. Issue resolution (rapid response to problems)
6. Wave retrospective (learnings for next wave)

Typical wave sizing:

• Wave 1: 25-50 users (early adopters, non-critical)
• Wave 2: 100-200 users (main population, multiple iterations)
• Wave 3: Remaining users (complex cases, executives)

Issue Escalation

Establish clear escalation paths:

War room during critical periods:

• Dedicated migration support during first 48 hours of each wave
• Clear escalation contacts
• Decision authority for real-time issues

Phase 5: Completion and Optimization

Workspace Decommissioning

Checklist:

• All users migrated and confirmed
• All data transferred and verified
• Integrations reconnected to new platform
• External sharing transitioned
• Domain MX records updated
• Archive requirements satisfied
• License count reduced/cancelled

Timeline considerations:

• Keep Workspace active for 30-90 days post-migration for stragglers
• Export any remaining data before cancellation
• Verify Google Takeout captures everything needed

Post-Migration Optimization

30-day review:

• User satisfaction survey
• Issue pattern analysis
• Performance metrics comparison
• Training gap identification

90-day review:

• Productivity impact assessment
• Cost comparison vs. projection
• Lessons learned documentation
• Platform optimization opportunities

Migration Risks and Mitigations

Risk: Data Loss

Mitigation:

• Full backup before migration
• Verification checks at each stage
• Rollback plan if issues emerge
• Extended retention on source platform

Risk: Extended Downtime

Mitigation:

• Off-hours migration windows for critical users
• Parallel access period where possible
• Clear communication of expected disruption
• Rapid escalation paths

Risk: User Adoption Failure

Mitigation:

• Comprehensive training before and during
• Super-user support network
• Clear escalation for issues
• Executive sponsorship visibility

Risk: Integration Breaks

Mitigation:

• Complete integration inventory
• Testing in pilot phase
• Staged reconnection with verification
• Fallback processes for critical integrations

When to Get Help

Self-Managed Migration Works When:

• Organization < 100 users
• Simple data footprint
• Limited external sharing
• Few custom integrations
• Strong internal IT capability

Professional Help Recommended When:

• Organization > 200 users
• Complex compliance requirements
• Extensive external sharing
• Many custom integrations
• Limited internal migration experience

Professional services options:

• Migration tool vendors (BitTitan, etc.)
• Platform vendors (Microsoft, etc.)
• Independent migration consultants
• Managed IT providers

Experience Your Migration Destination

Migrating from Google Workspace? Waymaker Commander brings email, documents, projects, and strategy together—a consolidation destination that reduces total tool count rather than substituting one suite for another.

The result: Migration to a platform designed for organizational intelligence, not just productivity apps.

Register for the beta and explore what's possible beyond traditional productivity suites.

---

Google Workspace migration is achievable with proper planning. The keys are thorough assessment, realistic timelines, strong change management, and phased execution that allows learning. Whether migrating to Microsoft 365, unified platforms, or hybrid solutions, the principles remain consistent. Invest in planning, support users through change, and optimize after migration. Learn more about what teams discover after leaving Workspace and explore how platform consolidation creates lasting value.

---

The Waymaker Editorial team has documented migration patterns from 200+ organizations. This guide synthesizes best practices for successful Workspace transitions.