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What is one of the most important decisions IT departments face in today’s cloud-first world? It’s not whether to leverage the cloud or to build a private cloud or even which cloud services to use. The more important decision is which applications to place in the cloud. Clearly, the best place to start is with new applications that are customer-, partner- and employee-facing. The harder challenge is what to do with existing applications.

Sadly these decisions aren’t often made objectively. Too often when making these decisions politics, assumptions about business value, emotion and bravado often cloud the decision process. “Our SAP implementation is a total pain to manage and maintain – it’s a bloated beast. Let’s move that to the cloud,” one CIO said to me back when I worked at Forrester Research. His belief was if they could move that app to the cloud it will prove to the organization that they could move anything to the cloud. Sadly, while a big bang certainly would garner a lot of attention, the likelihood that successfully transitioning that application (to any true cloud platform, frankly) would be extremely low due to architectural and integration complexities. And a big bang effort that becomes a big disaster could sour your organization on the cloud and destroy IT’s credibility. Instead, organizations should start with low risk applications that let you learn safely how to best leverage the cloud.

But how do you get the emotion, conjecture and bravado out of the process?

This requires a methodology and tool for framing the discussion and grounding it in best practices. And by the way, this decision process isn’t unique to the cloud decision. The overall decision is one of getting outsourcing right because some applications should move to true cloud platforms, others should transition to SaaS, while others are a better fit for traditional hosting, colocation and other deployment methods. Getting this right requires an objective third party or objective methodology and tool that helps you analyze your portfolio based on architectural fit, business agility needs, integration complexities and economics.

At Forrester we built such a tool for this, called the “strategic rightsourcing methodology,” based on best practice efforts from over 200 customers. But the leading global service providers and business consultancies who support The Microsoft Cloud have similar methodologies they can bring to your organizations. Whichever you choose, make sure it provides a structured set of questions that help your organization objectively break down your application and IT service portfolio using architectural and business fit criteria, into not only candidates for the cloud but also phases of consideration that let you achieve measurable and meaningful wins while gaining the experience necessary to move up from non-critical applications toward mission critical ones with the knowledge and confidence that they will succeed.

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