You launched a new platform. Modern architecture. Better performance. Lower costs.
Your existing customers stay on the old system because migration is scary, complex, and risky.
Six months later: 95% of customers haven't migrated. New platform adoption is stalled.
The Migration Reluctance Problem
Why customers don't migrate even when new platform is objectively better:
Fear of downtime: "If it ain't broke, don't fix it" Perceived complexity: "This will take months and cost a fortune" Institutional inertia: "We have other priorities" Risk aversion: "What if something breaks?" Hidden costs: "Migration itself is work we don't want to do"
Salesforce's Classic to Lightning migration insight (2015-2020):
Lightning was faster, better, more modern. Took 5+ years to migrate majority of customers.
Not because Lightning wasn't better. Because migration is hard.
Stripe's "Upgrade to Checkout" Migration
2019 problem: Stripe had old Checkout (deprecated) and new Checkout Sessions (modern, better).
Needed to migrate 500K+ integrations from old to new.
The strategy:
Phase 1: Make new option obviously better (6 months)
- Launch new Checkout with clear advantages
- Show side-by-side comparison
- Document performance improvements
- Publish success stories
- Make new API easier to implement than old
Phase 2: Incentivize early migration (3 months)
- Feature parity guarantees
- Early access to new features
- Migration support from solutions engineers
- Priority support for migrators
- Slack channel for migration questions
Phase 3: Gradual pressure (12 months)
- New features only on new platform
- Old platform enters "maintenance mode"
- Communication: "You can stay, but you'll miss out"
- Regular updates on adoption (social proof)
Phase 4: Deprecation timeline (12 months notice)
- Clear end date announced
- Regular email reminders
- Escalating urgency
- White-glove support for stragglers
- Final deadline enforced
Results:
- 70% migrated voluntarily (Phases 1-2)
- 25% migrated under pressure (Phase 3)
- 5% migrated at deadline (Phase 4)
- Customer satisfaction: 7.5/10 (could have been disaster)
The principle: Make migration easy and beneficial, then create urgency.
AWS's EC2-Classic to VPC Migration
AWS's biggest migration challenge: Moving millions of instances from EC2-Classic to VPC.
The complexity:
- Every customer affected
- Billions of dollars in workloads
- Zero-downtime requirement
- Complex networking changes
AWS's phased approach (2013-2022):
2013: Launch better alternative
- VPC offers better networking, security, features
- All new accounts default to VPC
- Existing customers can use both
2013-2019: Make VPC obviously superior
- New features only in VPC
- Document benefits extensively
- Provide migration tools and guides
- No pressure, just better option available
2019: Announce deprecation timeline
- "EC2-Classic will be retired in 2022"
- 3-year notice period
- Detailed migration guides per use case
- Automated migration tools
- Support commitment
2020-2021: Assisted migration
- AWS Solutions Architects help plan migrations
- Free migration workshops
- Migration checklist and readiness tools
- Regular communication and reminders
- Customer success stories
2022: Enforcement
- EC2-Classic actually deprecated
- Remaining customers forced to migrate
- White-glove service for complex cases
Lessons:
- Long timeline (9 years total) prevented revolt
- Made new option obviously better (no debate)
- Provided extensive migration support
- Clear communication throughout
- Enforced deadline (migrations wouldn't happen otherwise)
Shopify's "Upgrade to Online Store 2.0" Strategy
2021: Shopify launched Online Store 2.0 (modern theme architecture).
The migration challenge: 1.7M merchants on old themes.
What Shopify did differently:
1. Backwards compatibility (reduce risk)
- Old themes kept working indefinitely
- No forced migration
- Merchants choose when to move
2. Clear upgrade paths
- Each old theme → recommended new theme
- Visual comparison tools
- Data migration automated
- One-click migration where possible
3. Partner ecosystem enablement
- Train theme developers on OS 2.0
- Certification for migration services
- Partner directory for migration help
- Revenue opportunity for ecosystem
4. Staged rollout
- New stores: OS 2.0 only
- Existing stores: Opt-in to OS 2.0
- Power users: Early access and feedback
- Everyone else: When ready
5. Feature gates (create pull)
- New features only available in OS 2.0
- Better performance (provable)
- Easier customization (clear benefit)
- Future-proofing message
Results after 2 years:
- 60% of stores migrated
- 90% of new themes built on OS 2.0
- Merchant satisfaction high (voluntary adoption)
- No major migration disasters
The insight: When possible, don't force migration. Make new platform so much better they choose to migrate.
The Migration Communication Playbook
How to communicate platform migrations without causing panic:
DO:
- Give long notice (12-24 months minimum)
- Explain benefits clearly
- Provide migration resources
- Offer support and guidance
- Share success stories
- Set clear timeline and deadlines
DON'T:
- Spring migration on customers suddenly
- Use fear as only motivator
- Abandon old platform immediately
- Provide inadequate documentation
- Ignore customer concerns
- Keep changing the timeline
Twilio's migration email strategy:
T-12 months: Announcement Subject: "Introducing New Programmable Voice API"
- Here's what's new and better
- No action required yet
- Migration resources available
- We're here to help
T-9 months: Benefits focus Subject: "See what's possible with new Voice API"
- Customer success stories
- Feature comparisons
- Performance data
- Invite to webinar
T-6 months: Timeline reminder Subject: "Plan your migration to new Voice API"
- Reminder of benefits
- Deprecation timeline reconfirmed
- Migration guide and checklist
- Office hours and support options
T-3 months: Urgency builds Subject: "3 months until Voice API v1 deprecation"
- Reminder of deadline
- Migration status (if trackable)
- Last chance for support programs
- FAQ addressing concerns
T-1 month: Final push Subject: "Final reminder: Migrate by [date]"
- Clear deadline
- What happens if you don't migrate
- Emergency support contact
- One-on-one migration assistance
T-0: Deadline enforcement Subject: "Voice API v1 has been deprecated"
- Old API no longer available
- Emergency migration support
- Contact information for help
The cadence: Regular, clear, escalating urgency.
Migration Tooling and Automation
Manual migrations don't scale. Build tools.
Heroku's stack upgrade automation:
Old approach (2010-2014):
- Customer manually creates new app
- Customer migrates code and data
- Customer updates DNS
- Customer decommissions old app
- Time: 4-8 hours per app
- Error rate: ~25%
New approach (2015+):
- One-click stack upgrade button
- Automated code migration
- Automated database migration
- Automated DNS cutover
- Rollback option if issues
- Time: 5-15 minutes per app
- Error rate: <2%
Result: 10x more customers migrated successfully.
MongoDB's migration tools:
Database migration utilities:
- Schema analyzer (detects issues pre-migration)
- Data migration tools (automated copy with validation)
- Performance comparison (before vs. after)
- Rollback capability (safety net)
- Validation tools (ensure data integrity)
The principle: Reduce migration from "project" to "task."
Segment Migration by Risk
Not all customers can/should migrate at once.
Salesforce's Lightning migration segmentation:
Segment 1: Low-risk early adopters (30%)
- Simple configurations
- Enthusiastic about new features
- Tech-savvy users
- Strategy: Enable immediately, provide support
Segment 2: Moderate-risk willing (40%)
- More complex setups
- See benefits but cautious
- Need more hand-holding
- Strategy: Assisted migration, best practices, success stories
Segment 3: High-risk reluctant (20%)
- Very complex configurations
- Risk-averse organizations
- Legacy workflows
- Strategy: White-glove service, dedicated support, custom solutions
Segment 4: Mission-critical (10%)
- Cannot afford downtime
- Extremely complex
- High-value customers
- Strategy: Custom migration plans, dedicated team, phased approach
The approach: Different playbooks for different customer types.
The "Dual-Run" Migration Pattern
For critical workloads, running old and new in parallel reduces risk.
AWS's blue-green deployment pattern:
Phase 1: Build new environment (weeks-months)
- Set up new platform version
- Configure settings
- Test thoroughly
- Don't touch production yet
Phase 2: Parallel operation (days-weeks)
- Route small percentage of traffic to new platform
- Compare results old vs. new
- Identify issues without risk
- Increase traffic gradually
Phase 3: Full cutover (hours-days)
- Switch all traffic to new platform
- Monitor closely
- Old platform remains warm (can switch back)
- Decomission old after confidence period
Used for: Database migrations, API version upgrades, infrastructure changes
Success rate: 95%+ compared to 60% for direct cutover.
Handling Migration Failures
Even with perfect planning, some migrations fail. Have a plan.
Rollback procedures:
- Can you revert to old platform?
- How quickly can you rollback?
- What data might be lost?
- Communication plan for rollback?
Stripe's migration failure protocol:
Tier 1: Automatic rollback (minutes)
- Monitoring detects failure
- Automatic revert to old system
- Customer notified of temporary issue
- Investigation begins
Tier 2: Manual intervention (hours)
- Customer reports migration issue
- Engineer investigates
- Fix forward or rollback decision
- Customer kept informed throughout
Tier 3: Custom recovery (days)
- Complex migration issue
- Dedicated engineering team
- Custom solution developed
- Priority support until resolved
The commitment: No customer left broken.
Migration Success Metrics
How to measure if migration is working:
Adoption metrics:
- Percentage of customers migrated
- Migration velocity (per week/month)
- Time to complete migration (average)
- Self-serve vs. assisted migrations
Quality metrics:
- Migration success rate (first attempt)
- Rollback rate
- Support tickets per migration
- Customer satisfaction scores
Business metrics:
- Customer churn during migration
- Revenue impact
- Support cost per migration
- Time to deprecate old platform
MongoDB migration dashboard:
- Total customers: 50,000
- Migrated: 35,000 (70%)
- In progress: 5,000 (10%)
- Not started: 10,000 (20%)
- Target date: 6 months
- On track: Yes ✓
Review weekly. Adjust strategy based on data.
The "Choose Your Own Timing" Strategy
When possible, let customers migrate when ready (within window).
GitHub's migration approach:
Old: GitHub Enterprise 2.x (on-premises) New: GitHub Enterprise 3.x (cloud or on-prem)
The strategy:
- Announce: "3.x is available now, 2.x supported until [date 2 years out]"
- Benefits: Clear advantages of 3.x
- Timeline: Customer chooses when in 2-year window
- Support: Available for both during window
- Deadline: After 2 years, 2.x unsupported
Result:
- Customers migrate when convenient for them
- Less panicked migrations
- Higher success rate
- Lower support burden (spread over time)
The insight: Forced migrations cause chaos. Timed windows reduce stress.
Post-Migration Optimization
Migration isn't the end. It's the beginning.
Post-migration playbook:
Week 1: Immediate validation
- Functionality check
- Performance baseline
- User acceptance
- Quick wins identification
Month 1: Optimization
- Fine-tune configurations
- Address user feedback
- Enable advanced features
- Measure improvements
Month 3: Expansion
- Adopt new platform features
- Optimize workflows
- Training on new capabilities
- Share success internally
Shopify's post-migration engagement:
- Email: "You've upgraded! Here's what's new"
- Tutorial: "5 things you can now do"
- Webinar: "Maximizing Online Store 2.0"
- Survey: "How was your migration experience?"
The goal: Ensure customers realize benefits and don't regret migration.
When Migrations Go Wrong
Case study: Heroku's failed forced migration (2015)
Heroku tried to force all customers off deprecated stack with 6-month notice.
What went wrong:
- Timeline too short for enterprise customers
- Migration tools had bugs
- Support couldn't handle volume
- Communication felt aggressive
- Community backlash
The result:
- Extended deadline by 12 months
- Apologized publicly
- Improved migration tools
- Added more support resources
- Learned costly lesson
The lesson: Migrations require patience, empathy, and resources. Rush it, pay the price.
Migration as Growth Opportunity
Best-case: Migration improves customer relationships.
When done right:
- Customers appreciate new capabilities
- Support interaction builds trust
- Success stories create advocates
- Modernized base enables innovation
Salesforce post-Lightning migration:
- Higher customer satisfaction (faster platform)
- Increased feature adoption (better UI)
- Lower support costs (better tooling)
- Accelerated innovation (modern foundation)
The realization: Good migrations aren't just necessary evil. They're relationship-building opportunities.
Platform migrations will always be hard.
But they don't have to be disasters.
Plan long. Communicate clearly. Provide support. Enforce deadlines.
That's how you migrate thousands of customers without losing them.