Migration Readiness Assessment

Step 1: Gather context

What workload are you planning to migrate? Please share:

• Current environment (on-premises, other cloud, colocation)
• Application stack (languages, frameworks, databases, middleware)
• Dependencies (other systems it talks to, shared databases, network requirements)
• Business drivers (cost, agility, compliance, end-of-life hardware, etc.)
• Timeline constraints (optional)

Step 2: Determine migration strategy (7 Rs)

Step 3: Assess readiness by pillar

• 🟢 Ready — no blockers, can proceed
• 🟡 Conditionally Ready — gaps exist but can be addressed during migration
• 🔴 Not Ready — blockers must be resolved before migration

Operational Excellence

• Is there IaC for the current environment? Can it be adapted?
• Are CI/CD pipelines in place?
• Is monitoring portable or cloud-specific?
• Are operational runbooks documented?

Security

• Are there compliance requirements that affect region/service choice?
• How are secrets and certificates managed today?
• Are there network security dependencies (firewalls, IDS) that need equivalents?
• Is identity federation in place or needed?

Reliability

• What is the current availability? What's the target post-migration?
• Are there HA/DR mechanisms that need to be replicated?
• What's the acceptable downtime during migration?
• Are backups and recovery procedures tested?

Performance Efficiency

• Are there latency-sensitive integrations?
• Are there hardware-specific dependencies (GPUs, FPGAs, specific CPU)?
• What are the current performance baselines?
• Are there performance SLAs that must be maintained during cutover?

Cost Optimization

• What's the current TCO?
• What's the expected AWS cost? (rough estimate)
• Are there licensing implications? (BYOL, license-included)
• Are there existing commitments (contracts, prepaid licenses)?

Sustainability

• Can the migration reduce resource footprint?
• Are there opportunities to use Graviton or serverless?
• Can managed services replace self-managed infrastructure?

Step 4: Identify risks and blockers

• 🔴 High Risk — can block migration or cause failure
• 🟡 Medium Risk — increases effort or timeline but manageable
• 🟢 Low Risk — minor impact, address during optimization

• Hard dependencies on on-premises systems that can't move yet
• Licensing restrictions (Oracle, Windows, third-party software)
• Data residency or sovereignty requirements
• Large data volumes requiring transfer planning (Snowball, DataSync, DMS)
• Skills gaps in the team
• Compliance re-certification requirements
• Performance-sensitive integrations with on-premises systems

Step 5: Produce the assessment

# Migration Readiness Assessment: {Workload Name}

## Summary
- **Recommended strategy**: {strategy}
- **Overall readiness**: {Ready / Conditionally Ready / Not Ready}
- **Estimated effort**: {T-shirt size with justification}
- **Key risks**: {top 2-3}
- **Estimated timeline**: {weeks/months}

## Migration Strategy Rationale
{Why this strategy fits the workload and business drivers}

## Readiness Scorecard
| Pillar | Readiness | Score (1-5) | Key Gap |
|--------|-----------|-------------|---------|
| Operational Excellence | 🟢/🟡/🔴 | {score} | {gap} |
| Security | 🟢/🟡/🔴 | {score} | {gap} |
| Reliability | 🟢/🟡/🔴 | {score} | {gap} |
| Performance Efficiency | 🟢/🟡/🔴 | {score} | {gap} |
| Cost Optimization | 🟢/🟡/🔴 | {score} | {gap} |
| Sustainability | 🟢/🟡/🔴 | {score} | {gap} |

## Risks and Blockers
| Risk | Severity | Impact | Mitigation | AWS Service |
|------|----------|--------|------------|-------------|
| {risk} | 🔴/🟡/🟢 | {impact} | {mitigation} | {service} |

## Pre-Migration Checklist
{What must be done before migration starts, ordered by priority}

## Migration Plan

### Phase 1: Assess & Mobilize (Weeks 1-2)
{Discovery, dependency mapping, landing zone setup}

### Phase 2: Migrate (Weeks 3-6)
{Data migration, application migration, testing}

### Phase 3: Optimize (Weeks 7-8)
{Right-sizing, cost optimization, performance tuning}

## AWS Services for Migration
| Category | Service | Purpose |
|----------|---------|---------|
| Server migration | AWS MGN | Rehost EC2 workloads |
| Database migration | AWS DMS | Replicate databases with minimal downtime |
| Data transfer | DataSync / Snowball | Large-scale data movement |
| Schema conversion | AWS SCT | Convert database schemas |
| Network | Direct Connect / VPN | Hybrid connectivity |
| Landing zone | Control Tower | Multi-account governance |

## Cost Comparison
| Category | Current (monthly) | Estimated AWS (monthly) | Savings |
|----------|-------------------|-------------------------|---------|
| Compute | {current} | {estimated} | {delta} |
| Storage | {current} | {estimated} | {delta} |
| Networking | {current} | {estimated} | {delta} |
| Licensing | {current} | {estimated} | {delta} |
| **Total** | {total} | {total} | {delta} |

Step 6: Offer follow-up

Would you like me to:

• Design the AWS landing zone architecture?
• Create a detailed data migration plan?
• Estimate AWS costs in more detail (instance mapping, storage tiers)?
• Build a pre-migration testing strategy?
• Identify quick wins to demonstrate value early?