A Practical Way To Plan And Track

De-Risk Your VMware Exit

VMware migrations are no longer a theoretical exercise. In recent client conversations, I see infrastructure and operations leaders actively reassessing their VMware environments, driven by cost pressure, licensing uncertainty, and broader platform modernization goals. But most fall into the trap of having no thorough plan.

That’s exactly why I published Forrester’s VMware Migration Checklist. This report provides self-service guidance in the form of a practical checklist that helps teams plan their VMware migrations, track progress, and reduce risk across the journey.

Why A Checklist Matters More Than A Platform Decision

A pattern I see repeatedly is teams jumping straight to selecting a target platform — another hypervisor, public cloud, or managed service — without first understanding the dependencies and not enough clarity on what actually needs to move. In one example, a client had already initiated proofs of concept with multiple vendors before realizing that nearly 30% of their VMware estate could simply be maintained as is for the next two years. In another case, a team migrated workloads successfully but struggled post-cutover because operational ownership and support models were never clarified.

A checklist forces discipline. It helps teams slow down just enough to ask the right questions early:

Which workloads should be maintained, migrated, or modernized?

What application, data, security, and operational dependencies exist?

What does success look like beyond “VMs have moved”?

Framing The Journey: Maintain, Migrate, Modernize

I frame a CIO/VP of infrastructure and operations-based VMware decision this way: maintain, migrate, or modernize. Not every workload should move, and not every migration should result in modernization. The checklist helps teams categorize workloads intentionally:

Maintain workloads that are stable, low-risk, or nearing retirement.

Migrate workloads that benefit from platform change but minimal refactoring.

Modernize workloads where cloud-native services, containers, or architectural change deliver clear business value.

This framing reduces unnecessary disruption and ensures that migration decisions are driven by outcomes, not urgency.

From Readiness To Execution — And Beyond

The checklist spans the full lifecycle of a VMware migration:

Readiness and discovery: inventory, dependency mapping, skills, and risk assessment

Planning and sequencing: workload prioritization, migration waves, and success criteria

Execution and validation: tracking progress beyond infrastructure cutover

Post-migration operations: cost control, performance, resilience, and support readiness

This checklist is best used as a shared artifact across infrastructure, security, application, and finance teams. A shared view creates alignment, accelerates decision-making, and reduces last-minute surprises.

Built For Real-World Constraints

This is not a “big bang” or rip-and-replace playbook. The checklist assumes hybrid environments, constrained timelines, and mixed outcomes. Some workloads move quickly, others pause, and some never move at all. That’s reality, and my guidance is to work within it.

If you’re early in your VMware migration planning, already midflight, or feeling stuck, Forrester’s VMware Migration Checklist can help you regain control and bring structure to your approach.

If you want to go deeper and pressure-test your migration strategy, validate workload decisions, or apply this checklist to your specific environment, I encourage you to schedule an inquiry call or guidance session with me.