You've decided to consolidate your productivity stack. You're tired of paying for two overlapping ecosystems. You want one platform that actually works.
But here's the question nobody wants to answer: Which legacy suite should you leave first?
Both Google and Microsoft are pushing aggressive pricing. Both are forcing AI bundles you didn't ask for. Both have gaps that require additional tools to fill.
After helping organizations navigate this decision, here's the framework for choosing which to leave first.
The State of Both Platforms in 2026
Google Workspace
Price trajectory: Up 40% in two years (2024-2026)
- Business Starter: $6 → $7.20 → projected $8+
- Business Standard: $12 → $14 → projected $16+
- Mandatory AI add-ons coming for enterprise tiers
Strengths:
- Superior real-time collaboration
- Clean, intuitive interface
- Strong search across all content
- Better mobile experience
Weaknesses:
- Limited offline capabilities
- Weaker document formatting (complex docs)
- No native project management
- Limited enterprise features without add-ons
Microsoft 365
Price trajectory: AI bundling driving costs up
- Business Basic: $6/user/month
- Business Standard: $12.50/user/month
- Copilot add-on: $30/user/month (often required for enterprise)
Strengths:
- Deep document formatting capabilities
- Better desktop app experience
- Stronger enterprise integrations
- More robust offline mode
Weaknesses:
- Clunky real-time collaboration
- Complex, legacy-feeling interface
- Teams fatigue is real
- Heavy system requirements
The Decision Framework
Factor 1: Where Does Your Team Actually Work?
Leave Google first if:
- Your team primarily works on desktop applications
- Complex document formatting is critical (legal, publishing, finance)
- You need robust offline access for field teams
- Your industry runs on Microsoft (government, enterprise partners)
Leave Microsoft first if:
- Your team works primarily in browsers
- Real-time collaboration is essential
- You have a mobile-first workforce
- Simplicity trumps feature depth
Factor 2: What's Your Data Gravity?
"Data gravity" is where your critical business information lives. This determines migration complexity.
Google data gravity indicators:
- Gmail is your primary business communication
- Google Drive holds your institutional knowledge
- Google Sheets power your operations
- Calendar is deeply integrated with everything
Microsoft data gravity indicators:
- Outlook calendars drive your scheduling
- SharePoint holds your document management
- Excel models run your business
- Teams channels are where work happens
The rule: Leave the platform with less data gravity first. It's easier to migrate smaller data sets.
Factor 3: Integration Dependencies
Map your integrations for both platforms:
Google integrations:
- Which tools sync with Google Calendar?
- What pulls from Gmail?
- Where does Drive data flow?
Microsoft integrations:
- What connects to SharePoint?
- Which tools depend on Teams?
- Where does Outlook data flow?
The platform with fewer critical integrations is easier to leave.
Factor 4: Team Sentiment
Ask your team directly:
- Which platform do they prefer?
- Where do they spend most time?
- What causes the most frustration?
Leaving the less-preferred platform reduces change resistance.
The Migration Priority Matrix
| Factor | Leave Google First | Leave Microsoft First |
|---|---|---|
| Work style | Desktop-heavy | Browser-first |
| Data gravity | Less in Google | Less in Microsoft |
| Integrations | Fewer Google deps | Fewer Microsoft deps |
| Team sentiment | Prefers Microsoft | Prefers Google |
| Industry | Microsoft-dominated | Google-friendly |
| Document needs | Complex formatting | Simple collaboration |
Score your situation: Count which column has more checkmarks. That's your migration priority.
The Case for Leaving Both
Here's what most analyses miss: you don't have to keep either.
The question isn't really "Google or Microsoft?" It's "do we need legacy productivity suites at all?"
Modern unified platforms provide:
- Email, calendar, documents, sheets, presentations
- Project management and goal tracking
- Team communication and collaboration
- AI that understands your organizational context
All without the baggage of 20-year-old architectures.
Why Legacy Suites Became Expensive
Google and Microsoft aren't raising prices because costs increased. They're raising prices because:
- Market saturation: Growth from new customers slowed
- AI arms race: Both need to fund massive AI investments
- Captive audiences: Switching costs keep customers trapped
- Shareholder pressure: Revenue growth must come from somewhere
You're funding their AI research whether you use it or not.
The Unified Alternative
Instead of choosing which legacy platform to leave first, consider leaving both for a platform built for 2026:
What you gain:
- Single subscription instead of two (or twenty)
- Native integration across all tools
- AI that actually knows your business
- Modern architecture without legacy debt
What you leave behind:
- Dual subscription costs
- Integration maintenance
- Context switching between ecosystems
- Forced AI bundle pricing
The Practical Migration Path
If Leaving Google First
Week 1-2: Prepare
- Export all Google Drive data
- Document Gmail filters and settings
- Map Google Calendar integrations
- Inventory Google Sheets automations
Week 3-4: Migrate
- Import documents to new platform
- Redirect email (or migrate fully)
- Reconnect calendar integrations
- Rebuild critical sheet workflows
Week 5-6: Transition
- Run parallel systems
- Train team on new workflows
- Sunset Google tools progressively
- Cancel subscription at renewal
If Leaving Microsoft First
Week 1-2: Prepare
- Export SharePoint document libraries
- Archive Teams conversations (if needed)
- Document Outlook rules and delegates
- Map Excel dependencies
Week 3-4: Migrate
- Import documents to new platform
- Migrate or redirect email
- Reconnect calendar systems
- Recreate essential Excel logic
Week 5-6: Transition
- Parallel operation period
- Team training and support
- Progressive shutdown of Microsoft tools
- Cancel at contract end
Common Migration Mistakes
Mistake 1: Migrating Everything
Don't move data that doesn't matter. Before migration:
- Archive completed projects
- Delete outdated documents
- Clean up abandoned folders
Migrate only what you'll actually use.
Mistake 2: Rushing the Timeline
Rushing creates chaos. Better to:
- Plan thoroughly
- Allow overlap periods
- Support struggling users
- Iterate on problems
Mistake 3: Ignoring Change Management
Technology migration is easy. People migration is hard.
- Communicate the "why" clearly
- Involve team in planning
- Provide adequate training
- Celebrate early wins
Mistake 4: Not Questioning the Premise
The biggest mistake: assuming you must keep one legacy suite.
Question every assumption:
- Do we need Google OR Microsoft?
- Could we use neither?
- What would we choose if starting fresh?
The Real Question
Whether you leave Google or Microsoft first matters less than this: Are you moving toward something better, or just rearranging deck chairs?
Migrating from Google to Microsoft (or vice versa) just trades one set of problems for another. You're still:
- Paying premium prices for partial solutions
- Maintaining integrations between tools
- Dealing with forced AI bundles
- Trapped in legacy architectures
The organizations thriving in 2026 asked a different question: "What if we could have everything in one place, built for how we work today?"
That question leads to unified platforms. Not legacy suites.
Ready to explore your options? See why companies are leaving Google Workspace or learn about unified productivity platforms.
About the Author
Stuart Leo
Stuart Leo founded Waymaker to solve a problem he kept seeing: businesses losing critical knowledge as they grow. He wrote Resolute to help leaders navigate change, lead with purpose, and build indestructible organizations. When he's not building software, he's enjoying the sand, surf, and open spaces of Australia.