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My co-author, Barry Briggs, and I have just published the second edition of our free eBook Enterprise Cloud Strategy, which aggregates the experience we have seen of hundreds of IT environments and their migration process to the cloud. In the book, we highlight the approach, strategy, best practices and processes followed by IT in their effort to migrate their enterprise portfolio to the cloud, by answering the most common questions: “How and where do I start?”, “How do I build a plan for cloud migration for my application portfolio?” and “How will my organization be affected by this change?”

Preparing for the Journey

Before you begin a cloud transformation, help your customers understand the new IT mindsets that need to evolve during their journey. The first shift is embracing a culture of innovation and experimentation, which can be a hard pill for some traditional IT shops to swallow. They’ll need to move away from a focus on carefully controlled development and risk reduction, and learn to envision, experiment, and optimize quickly, using the following principles:

  • Go fast – With the cloud, new projects can be spun up quickly with a few clicks. We call this the “try many/use best” approach.
  • Push the boundaries – Don’t simply adapt to the cloud, quickly adopt new architectures and processes to exploit new opportunities.
  • Make data-driven decisions – Carefully track and measure the numbers, including cost and system telemetry for technical efficiency.
  • Simplify – Retire, right-size, and consolidate as many services and applications as possible.
  • Communicate– Establish a clear and continuous communication channel for stakeholders to visualize success and impact to help them stay engaged.

Visualizing the Customer Journey

It’s important throughout this process to foster an attitude of opportunism. Your customers are learning from you how to envision new outcomes as their applications move to the cloud, but the beauty of this new landscape is that it will continue to surprise them with possibilities. Migration is a huge opportunity to modernize their IT ecosystem, looking at each application to determine its place in the new environment, or if further investment is even justified. Even for applications that remain on-premises, modernization can save time and money.

Application Modernization

There’s no single right approach for legacy applications but our adaptation of Gartner’s “5 R’s” (retire, replace, retain and wrap, re-host, and re-envision) provides a good way to approach the problem.

  • Retire – When a legacy application is providing little value compared to its costs, it’s a natural candidate for retirement. If some functionality is still deemed useful, it can be rolled into a consolidated modern application running in the cloud.
  • Replace – Many legacy applications were originally built because there was no alternative at that time. Modern applications better suited to running in the cloud might now exist, and there might be a chance to consolidate functionality from several older applications.
  • Retain, wrap, and expand – If a legacy application is providing good value and not incurring a high TCO, the best approach might be to retain it but put a modern “wrapper” around it in order to gain additional value and benefits.
  • Re-host – If a legacy application is providing good value but is expensive to run, it might be a candidate for re-hosting in the cloud where it is easier to manage and less expensive to run.
  • Re-envision – If a legacy application is providing good value but cannot be easily moved, the best solution might be to re-envision it and build it again in the cloud.

Regarding those waypoints, in our experience, there are three basic stages: experimentation, migration, and transformation. These stages can take place concurrently or in sequence, depending on the individual needs of the project or customer.


Whether it’s moving an existing application to the cloud or creating a new one, experimentation is essential to gain an understanding of what developing, testing, deploying, and maintaining a cloud application is all about.


In the migration stage, the bulk of the IT portfolio is moved to the cloud in one form or another. This requires cooperation and collaboration across several different enterprise functions, including the technical staff, the operations staff, the executive team, business sponsors, security professionals, regulatory compliance staff, legal, and HR.


In the transformation stage (which often overlaps with the migration phase), selected applications are redesigned to take maximum advantage of the cloud affording greater scale, greater integration with other cloud services, and numerous other advantages. The now-cloud-native applications can take advantage of cloud services such as machine learning, big data, streaming analytics, and many others—making them much, much richer in function and feature than before.

There is a lot more to talk about in preparing for the last two stages which I will dive into in subsequent posts. In the meantime, you can download the Enterprise Cloud Strategy eBook here.

How are you helping your customers migrate to the cloud? Share your process with the Microsoft Partner Community.