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Things to Consider in a Cloud Readiness Assessment

This is the next installment in a series of blogs on the subject of cloud transformation. It has been amazing to see how many clients have jumped straight from cloud mandate to cloud implementation. A very small, technical organization with a very limited separation of duties might be able to take this approach. However, this is not the case for any technical organization that has even a small amount of separation of duties. These organizations should spend some time on an upfront cloud readiness assessment to ensure a smooth transition. This assessment should cover all parts of the technical group and key stakeholders from the business groups. A little time spent on this assessment will return months of time and thousands of dollars in savings. In this blog, we will outline a high-level process and key areas of consideration for a basic cloud readiness assessment.

Cloud Readiness “Things to Consider”

At the very beginning of any organization’s journey to the cloud, the organization must evaluate its operations. Specifically, organizations must evaluate their business, people, process, and technology for readiness to move to the cloud. Everyone knows we can define “readiness” in many different ways. For our purpose, we will use the following definition or questions:

“Is your technology group in general ready to start deploying and supporting cloud-based solutions for your business operations? Specifically, do all of your individual functional areas in your technology group have the basic skills, focus, funding, and time to start moving on the cloud journey? “


You should meet with your key business operations stakeholders at the very start of any cloud readiness assessment. This should be both the internal business operations folks like finance, accounting, and HR, and external business operations like sales, marketing, and investor relations. One of the key items for review is to show the actual benefit of leveraging cloud technology over the current solutions in place to these groups. This is somewhat of an internal assessment for the person performing the assessment. First, this person will need to ask and listen for the “pain points” from each group. The assessor would then need to have knowledge of the cloud solutions that can minimize or eliminate those pain points. These pain points will become key guide post for the first step actions in the cloud migration planning.


Your current technology staff will be one of the first areas for review in your cloud readiness assessment. As human beings, we all have different tolerances for change, learning new things, and generally changing the way we execute our jobs. This review of current staff should include some high-level assessment of cloud technology skills, education, available time, and exposure.


Most technology groups will have some level of governance, compliance, and security requirements. The deployment of cloud technology will impact some of these processes. A cloud readiness assessment helps you gain a high level understanding of how many processes will be impacted. Once that’s established, you then need to establish how long will it take to draft and approve the critical changes required. Once again, the review in this area is at a very high level and should not get bogged down in trying to figure out the change. Instead, just note the need for change and process owners.


Many people would think this part might be the easiest part of a readiness assessment. However, this can actually be the hard part. When assessing your readiness, your current technology stack, including applications, infrastructure, and data, must be well understood. In our daily rush to get solutions in place, documentation is often not part of the project. This is what creates the challenge for this part of the assessment.

An assessment in this area needs to review your application portfolio at a very high level. This is designed to make a quick and rough estimate of how many applications might be able to move to the cloud. You shouldn’t focus on “how” the application would move. Instead, you simply need to ask if this is an application that could move to the cloud. Some applications are at or near end of life and others are simply outdated utilities that need to be replaced. Next, you need to evaluate your current infrastructure from the network layer all the way to the data center operations level.

We don’t recommend a manual approach. Instead, we prefer to leverage an automated migration planning tool with infrastructure discovery and reporting capabilities. The focus for this assessment is how would you leverage the cloud infrastructure with your on-premises infrastructure for any kind of deployment to the cloud. When making this assessment, you need to consider the level of difficulty and how many things would need to be changed or fixed with connectivity to the cloud provider. Almost all cloud migrations start out with a “hybrid” approach with some kind of direct connectivity to the cloud provider. Finally, you must complete a high-level review of all of your data assets from small, stand-alone databases to large-scale data warehouses. Much like the earlier review, this review should be focused on how many applications can be moved to the cloud. Don’t focus on the “how” – just focus on the number of the applications.


The cloud readiness assessment involves working through each of these areas in the shortest amount of time possible while still collecting the basic information required for each area. The final part of the assessment is to make some judgement calls by adding a time element to the analysis of the information collected. The time element will provide the ultimate answer about when you will be ready to continue with your cloud journey.

Some organizations will be ready move on immediately, while others might need to spend a little more time on changes. A side benefit of performing a brief cloud readiness assessment comes from the exposure to the whole organization that you are considering the move to cloud. The time spent performing a cloud readiness assessment at the front of your cloud journey will be some of the most valuable time in your cloud journey.


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Victor Wolters, Enterprise Strategist

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