It has taken years and finally the cloud is a reality. Enterprises, large and small, can and should eliminate major IT capital expenditures and also dramatically reduce operating expenses with higher service levels by migrating to the cloud. That is the story of IT today.

But how does a firm actually do it and how what are the challenges facing enterprises as they undertake these IT changes?

Level setting on terms and meaning is critical. Many, including many less sophisticated IT people prefer to think of the "cloud" as only public cloud services akin to Amazon Web Services. And AWS is indeed a great offering. But the fact is that the "cloud" can and does in fact mean many things. The term encompasses a range of usage-based models ranging from public and private clouds, to hybrids of those clouds and all of which may continue to leverage local services be it virtual or physical. Even at the services or vertical application the notion of all or nothing breaks down. For example, does Salesforce work for every firm for CRM, clearly not. Does it work for many firms and with a little effort and customization arguably most, yes it can. But does it follow that that same organization move immediately to analogous cloud based ERP or MRP systems, maybe, or maybe not.

In the end, it is always a trade off of costs and flexibility against a panoply of issues like security, availability and the like. And it will for certain be a hybrid story, and one that will employ multiple services delivered in differing ways, ideally working seamlessly together.

Life, and IT, is rarely all or nothing. Most importantly, as a business considers incorporating the cloud, it is critical for their organizations to assess and determine their core: (1) strengths, (2) constraints and (3) objectives, and then make appropriate cloud mobilization plans.

1.) From a core strengths perspective, if an organization has already invested in large IT organization and assets, then they are likely more both more conservative in motivation to change but also have the most to gain economically from cloud mobility. They have invested hardware and software assets with varying useful lives, which will come to an end in typically less than three years. They have access and are obligated under support agreements. But how to transition where there is risk of stranded and unsupported assets? For sure, these larger organizations often know how to manage these assets, largely have budget certainty and know what to expect.

2.) From a constraints perspective, it can be that place of "comfort" - namely don't worry the service is up and running now isn't it - which is most the concerning. In the world of IT, there is one thing which is certain and that is change. What patch or version are we on? Who knows how that stack was built? Are their unknown (or even known) IT vulnerabilities that ought to be addressed? If an organization has current IT staffing, do they have the core competencies to manage cloud operations, and if not, what is the training and staffing plan? Do all the IT resources make the transition and if not what happens to them? In some sense the cloud question, albeit a base technology question, has the most significant manifestations across the business itself. Evaluating these limits and impacts is critical.

3.) From an objectives perspective, given any set of operating strengths and constraints, a range of objectives should be established and organizationally agreed. Sure there are the obvious goals of lower capital expense and reduction of operating expenditures. But a detailed assessment of objectives, and the necessary plan for what an organization wants out of a cloud migration are far broader and far deeper. They are hardly trivial. For example, are their systemic weaknesses embedded in the current systems that need to be addressed and managed? Are their areas of tribal knowledge where risks are not fully understood or manageable? What happens when those services are migrated? Do they come up in the target environments? Who will support them? Is a roll back possible as a disaster recovery plan?

For sure this is one of those places in which the devil you know is better than the devil you don't. It is also fool hard to suggest that any generic "checklist" could represent the tasks most or even many organizations should look to in planning their business plan for migration. The bottom line is there is no substitute for a rigorous assessment of an organization's core IT strengths, constraints and objectives relative to the cloud, and then on that assessment make appropriate cloud mobilization plans. Document the process and the outcome and ensure business and organizational alignment.

In the end, the plan may be carried off over time but there is just no substitute for asking the hard questions, understanding the current and proposed approaches and then making an appropriate plan. And if your IT team isn't ready or able to do the kind of rigorous assessment of cloud mobility today then one ought to find an external team to do it. Rest assured your competitors are already on it.