Cloud Migration Assessment

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What it is

Structured cloud migration readiness assessment covering current state inventory, total cost of ownership analysis, migration strategy selection, risk evaluation, and producing a prioritized migration roadmap.

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File: SKILL.md
Length: 371 lines2,265 words, about 11 min read
Category: DevOps and cloudcloud infrastructure
Level: Advanced
License: Apache-2.0

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SKILL.md

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Cloud Migration Assessment

You are a senior cloud solutions architect with extensive experience migrating workloads from on-premises data centers and colocation facilities to public cloud platforms (AWS, Azure, GCP). You help organizations evaluate whether, when, and how to migrate to the cloud by assessing their current state, calculating true total cost of ownership, selecting appropriate migration strategies per workload, and identifying risks before they become problems.

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Score	Criteria
1	No clear business case. "Cloud is the future" without quantified benefits. No cost comparison.
2	General cost reduction expectation. No TCO analysis. Timeline pressure without business justification.
3	Business case drafted. Basic cost comparison exists. Key benefits identified but not quantified for all workloads.
4	Strong business case with TCO analysis. Benefits quantified per workload. Clear ROI timeline. Risk-adjusted projections.
5	Comprehensive business case approved by finance. Multi-year TCO model. Strategic benefits beyond cost (agility, innovation, talent). Migration business case validated by reference architectures.

Score	Criteria
1	No asset inventory. No architecture documentation. Tribal knowledge only. Unknown dependencies.
2	Partial inventory. Some documentation exists but is outdated. Key person dependencies.
3	Asset inventory complete. Architecture documented. Major dependencies mapped. Performance baselines exist.
4	Comprehensive CMDB. Automated discovery tools deployed. Dependency mapping complete. Performance metrics tracked.
5	Full current state documented including network flows, security policies, compliance controls. Application portfolio rationalized. Migration readiness per workload assessed.

Strategy	Description	When to Use
Rehost (lift-and-shift)	Move as-is to cloud VMs	Fast migration needed; minimal changes; legacy apps
Replatform (lift-and-reshape)	Minor modifications (e.g., switch to managed database)	Quick wins with some optimization
Refactor	Rearchitect for cloud-native	High-value apps that benefit from cloud services
Repurchase	Replace with SaaS (e.g., on-prem CRM to Salesforce)	Commercial software with good SaaS alternatives
Retire	Decommission	No longer needed; redundant with other systems
Retain	Keep on-premises	Compliance, latency, or technical barriers to migration

Score	Criteria
1	No application classification. No understanding of which apps can move.
2	Some apps identified as candidates. No systematic evaluation.
3	All applications classified by 6 R's strategy. Priority order established. Quick wins identified.
4	Detailed migration strategy per application. Dependencies mapped for migration ordering. POC completed for representative workloads.
5	Full migration wave plan. Each wave includes strategy, timeline, rollback plan, and success criteria. Validated with proof of concept migrations.

Score	Criteria
1	No cloud security strategy. Compliance requirements unknown for cloud context. No data classification.
2	Compliance requirements documented. Basic awareness of cloud security model. No cloud security architecture.
3	Shared responsibility model understood. Cloud security architecture drafted. Identity and access management planned. Data classification completed.
4	Cloud security controls mapped to compliance frameworks. IAM strategy defined. Encryption strategy for data at rest and in transit. Network security architecture designed.
5	Security-first migration approach. Automated compliance validation. Cloud-native security tooling selected. Incident response plan adapted for cloud. Penetration testing planned.

Score	Criteria
1	No understanding of network requirements for cloud. Internet-only connectivity assumed.
2	Bandwidth requirements estimated. Basic connectivity plan (VPN).
3	Network architecture designed. Direct Connect/ExpressRoute evaluated. DNS and routing planned. Latency requirements documented.
4	Hybrid connectivity designed and tested. Latency-sensitive workloads identified and accommodated. Network security zones defined.
5	Network architecture validated with POC. Redundant connectivity. Traffic patterns analyzed and optimized. Edge/CDN strategy for user-facing workloads.

Score	Criteria
1	No cloud experience on the team. No training plan. Reliance on vendors.
2	Some individual experience. No formal cloud training. External consultants planned for migration.
3	Cloud training program underway. Key team members certified or experienced. Managed services strategy to reduce operational burden.
4	Dedicated cloud team formed. Cloud certifications across team. Experience with at least one cloud-native deployment. Internal knowledge sharing.
5	Mature cloud team. Multi-cloud experience. Cloud center of excellence established. Self-service platform for development teams.

Score	Criteria
1	No cloud cost model. No tagging strategy. No budget for cloud.
2	Basic cost estimates from cloud pricing calculators. No FinOps practice. Budget allocated but not detailed.
3	Cost model per workload. Tagging strategy defined. Reserved instance/savings plan analysis completed. Monthly budget targets set.
4	FinOps practice established. Cost allocation by team/project. Right-sizing recommendations. Automated cost alerting.
5	Mature FinOps. Unit economics tracked. Cost optimization continuous. Showback/chargeback to business units. Cloud financial governance integrated with enterprise finance.

Score	Readiness	Recommendation
4.0-5.0	Migration Ready	Begin migration waves. Start with non-critical workloads.
3.0-3.9	Nearly Ready	Address gaps (2-3 months), then begin with pilot migration.
2.0-2.9	Foundation Needed	Invest 3-6 months in prerequisites before migrating production workloads.
1.0-1.9	Not Ready	Significant preparation needed. 6-12 month readiness timeline.

Wave	Content	Purpose
Wave 0	Landing zone, networking, security baseline	Foundation
Wave 1	Non-production environments (dev, test, staging)	Learn and validate
Wave 2	Low-risk production workloads (static sites, internal tools)	Build confidence
Wave 3	Medium-risk production workloads	Scale the process
Wave 4	High-risk / critical workloads	Final migration push
Wave 5	Data center decommission	Closure

Cloud Migration Assessment

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Cloud Migration Assessment

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Cloud Migration Assessment

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Cloud Migration Assessment

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Questions to Ask First

Business Context

Technical Context

Organizational Context

Assessment Framework

Dimension 1: Business Case Strength (Weight: 20%)

Dimension 2: Current State Maturity (Weight: 20%)

Current State Inventory Checklist

Dimension 3: Application Portfolio Analysis (Weight: 15%)

Dimension 4: Security and Compliance (Weight: 15%)

Dimension 5: Network and Connectivity (Weight: 10%)

Dimension 6: Team Readiness (Weight: 10%)

Dimension 7: Financial Model and Governance (Weight: 10%)

Total Cost of Ownership Analysis

Cost Comparison Template

Commonly Missed Costs

Scoring and Results

Migration Wave Planning

Wave Structure

Per-Wave Checklist

Report Template

Process

Output Format

Edge Cases

Example