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Transition Licensing to the Microsoft Cloud

The cloud is coming – be prepared with a proactive strategy.

  • There are many different ways to license, purchase, and deploy cloud products, making it challenging to know how to maximize the benefits for your organization.
  • Despite obvious advantages, there are many reasons why the cloud may not be a good choice for your organization at this point.
  • Microsoft – as well as your business leaders – are pushing the cloud. Don’t rush into a cloud transition without planning carefully.

Our Advice

Critical Insight

  • Document your position on the cloud – whether that means transitioning or not, make sure you can justify your position to the organization.
  • Once you’ve committed to the cloud, it’s difficult to go back to on-premise licensing. Be certain the cloud is a good fit before executing.
  • Most organizations are still at a stage where they can keep their on-premise licensing. This will likely change over the next couple of years – the cloud is imminent, if not inevitable. If the cloud doesn’t make sense now, start thinking about how you might make it work in the future.

Impact and Result

  • Make sure you understand what your organization needs and why, before you commit to moving to the cloud.
  • Complete cost calculations carefully as the cloud might end up costing significantly more. It could also end up costing around the same amount, making it an efficient option.
  • If there are significant barriers to cloud adoption, discuss and document them. You’ll need this documentation in three years when it’s time to renew your agreement.

Transition Licensing to the Microsoft Cloud Research & Tools

Start here – read the Executive Brief

Read our concise Executive Brief to find out why you should prepare for a transition to the Microsoft cloud, review Info-Tech’s methodology, and understand the four ways we can support you in completing this project.

1. Review and document current usage

Gather current Microsoft licensing and documentation, build an effective license position, and identify licensing shortfalls.

2. Map Microsoft’s cloud offerings to needs

Determine functionality requirements, model licensing costs, and assess and plan the transition.

3. Negotiate the cloud transition

Complete negotiation due diligence and leverage the organization’s unique position.

Member Testimonials

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Guided Implementation




Workshop: Transition Licensing to the Microsoft Cloud

Workshops offer an easy way to accelerate your project. If you are unable to do the project yourself, and a Guided Implementation isn't enough, we offer low-cost delivery of our project workshops. We take you through every phase of your project and ensure that you have a roadmap in place to complete your project successfully.

Module 1: Assemble and Review Documentation

The Purpose

  • Assemble licensing documentation.
  • Build effective licensing position (ELP).

Key Benefits Achieved

  • Licensing documentation identified and organized.
  • ELP created.




Assemble licensing documentation


Obtain and review Microsoft ELP

  • ELP

Identify Microsoft cloud options that align with your ELP and desired future state goals

  • Microsoft Cloud Product Price Modeler

Module 2: Identify and Review Current State vs. Future State

The Purpose

  • Align technology and business goals to workshop.

Key Benefits Achieved

  • Business and IT Microsoft licensing goals aligned.




Create cloud transition framework overview

  • Transition framework overview

Create transition timeline

  • Transition timeline

Map future state license options for cloud products

  • Hypothesized licensing options

Module 3: Analyze Gaps and Plan Cloud Licenses

The Purpose

  • Identify gaps in current licensing and identify ideal future state.

Key Benefits Achieved

  • Gaps in current licensing identified.
  • Ideal future state identified.




Identify gaps between on-premise current state and cloud/hybrid future state

  • Gap analysis assessment

Identify product license changes, requirements, and license rules


Model high-level cost impact

  • Pricing estimator

Module 4: Develop Cloud Transition Strategy Options

The Purpose

  • Create transition strategy.

Key Benefits Achieved

  • Licensing transition planned and documented.




Document licensing migration paths for cloud/hybrid future state

  • Migration paths documented

Discuss migration options, costs, and overall license strategy


Develop cloud migration product list and action items

  • List of products and action items

Module 5: Present Cloud Transition Options and Costs

The Purpose

  • Presentation of cloud transition options and costs.

Key Benefits Achieved

  • Final deliverables.




Preparation of final deliverables


Finalize viable migration options and costs

  • Final report and strategy document

About Info-Tech

Info-Tech Research Group is the world’s fastest-growing information technology research and advisory company, proudly serving over 30,000 IT professionals.

We produce unbiased and highly relevant research to help CIOs and IT leaders make strategic, timely, and well-informed decisions. We partner closely with IT teams to provide everything they need, from actionable tools to analyst guidance, ensuring they deliver measurable results for their organizations.

What Is a Blueprint?

A blueprint is designed to be a roadmap, containing a methodology and the tools and templates you need to solve your IT problems.

Each blueprint can be accompanied by a Guided Implementation that provides you access to our world-class analysts to help you get through the project.

Need Extra Help?
Speak With An Analyst

Get the help you need in this 3-phase advisory process. You'll receive 8 touchpoints with our researchers, all included in your membership.

Guided Implementation #1 - Review and document current license usage
  • Call #1 - Gather documentation
  • Call #2 - Build an ELP
  • Call #3 - Incorporate licensing shortfalls into cloud transition plan

Guided Implementation #2 - Map Microsoft’s cloud offerings to needs
  • Call #1 - Sort licensing groups by functional need
  • Call #2 - Model your licensing costs
  • Call #3 - Assess and plan your transition

Guided Implementation #3 - Negotiate your cloud transition
  • Call #1 - Negotiation due diligence
  • Call #2 - Leverage your unique position


Aadil Nanji

Scott Bickley

Laura Trabucco


  • Filip Lauwereys, ASIST
  • Josef Hans Lara, Licensing Guru at Big Bang Innovation Services Inc.
  • Paul DeGroot, Principal Consultant at Pica Communications
  • Karl O’Doherty, CEO at SAM360
  • 4 anonymous contributors
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