Cloud Readiness Assessment: A Complete Roadmap to Migration

A move to the cloud can come with promises of greater flexibility, ease, scalability, and modernization, but it doesn’t mean the migration process will be a breeze. Migrating to the cloud successfully requires proper planning and analysis before taking that first step. One of the best ways to evaluate your organization’s preparedness is by using a cloud readiness assessment framework. From there, you can build a migration roadmap that doesn’t leave anything to chance.

What is a Cloud Readiness Assessment?

A cloud readiness assessment can help businesses determine whether they’re ready to move to the cloud by working through a checklist. This cloud readiness assessment checklist should include an examination of what needs to be done (if anything) to the applications and data used by a business to prepare it for cloud migration. It can also help make a plan for migration that causes minimal interruption to “business as usual.”

Cloud Readiness Assessment Checklist

A thorough cloud readiness assessment checklist will include a discovery process, an evaluation of team resources, an understanding of current IT infrastructure, IT security & compliance considerations, operational readiness, and budget considerations.


Before you can define what readiness for migration looks like, your organization has to ensure the planned migration aligns with business objectives. This can include costs, cloud scalability, data resiliency, failover, remote collaboration, and so on. How quickly will you need to be able to expand or contract your cloud environment in the face of fluctuating demand? How would you like to insulate your organization from disaster, and what can cloud environments provide that your current infrastructure cannot? What would you like to continue in a cloud environment that’s already working with your present setup? Do team members need to be able to access certain applications on their mobile devices or other remote sites? Starting with stated objectives will ensure your cloud migration strategy doesn’t leave anything important by the wayside.

Team Resource Evaluation and Training

What internal resources are at your disposal? Where might you require additional training or talent? Assessing your internal skill sets, available funds, and unclaimed IT staff time can better illustrate gaps in your knowledge and processes. If you don’t have anyone who’s a cloud migration expert, or you plan on adding tools that no one internally has used, bringing in outside help may be necessary. A third-party provider could do everything from conducting the assessment and planning and implementing the migration to training your team.

Understanding Your IT Infrastructure

Chances are, some of your workloads will be easier to move to the cloud than others, and some may not need to move at all. You likely also have some workloads that can be eliminated at some point in the migration process. Applying the 7 R’s of cloud migration can categorize the workloads for you – more on that later.

IT Security & Compliance

What should move to the cloud may be partially or completely determined by the security and compliance requirements you have for your data. If you have strict regulatory requirements to meet for some of your data, it may make sense for it to stay in an on-premises framework. Weigh what you might want to do with public and private cloud alongside your compliance needs. Also, it’s important to determine if there are any end-user or end-customer requirements for migration timing.

Operational Readiness

This may sound obvious, but a major part of cloud readiness is making sure you’re operationally prepared for a migration. Consider the following questions:

  • Are teams ready to shift the way they do things in favor of progress?
  • What training might you have to do?
  • Who might you need to win over to make migration a success?
  • Do you have maintenance windows or moratoriums on when an outage can occur during migration?


A gap may exist between what you’d like to accomplish and what you have the resources to achieve, but the only way to know for sure is by budgeting out your migration plans:

  • Whether you’re planning on doing it all at once or in phases, what’s your desired timeline for completing your cloud migration project?
  • Who will be involved in the process?
  • Will you need to pay for outside help?
  • What’s the cost of any downtime you might experience, even if it’s minimal?
  • When you’re making the switch to new software, what’s the cost of licensing?
  • How much will cloud providers charge for the resources you need?
  • How much downtime can you handle?

The more you include in your budget scoping, the better you’ll understand the overall cost of the project.

Risks of Not Assessing Your Cloud Readiness

Maybe it feels like you don’t have time for a cloud readiness assessment before it’s time to make a migration. However, rushing into the process can open yourself up to preventable risks.

Excessive Downtime

Moving something without considering important dependencies can lead to unexpected and excessive downtime, decreasing productivity and output that can lead to a loss in revenue and overall trust. Oftentimes, the problem is bigger than the average cost of downtime for an hour or day of being out of commission. Bigger risks come from the ripple effects caused by the downtime itself.

Vendor Lock-in

Making a hasty decision and signing with a vendor before determining whether they’re the right partner for the job can lead to lock-in, either because of a long-term contract or due to sunk costs of migration and configuration.

Compliance Issues

Compliance should always be top-of-mind when choosing a cloud provider. Your industry and level of data sensitivity will determine your compliance requirements. Not exploring this could lead to incompatibility with government mandates.

Inability to Scale With Organizational Growth

If your organizational plan includes growth, you need to have cloud infrastructure that grows with you. Cloud readiness should also include a scope and a vision – where are you now and where do you plan to be in a few years? Can your cloud migration plans get you there?

Cybersecurity Vulnerabilities

Depending on the type of cloud service – such as storage services, Software as a Service (SaaS), or Platform as a Service (PaaS) – the cloud provider may have some responsibility for security. But don’t forget, security will always be a combined responsibility between you and the provider. Not knowing, or preparing, can lead to embarrassing and costly data breaches and lawsuits.

Failing to Plan For Complexity

These issues can be complicated in larger organizations or where a hybrid cloud adoption is underway. Migrating to multiple cloud providers or to a hybrid on-premises and cloud environment requires interoperability and, often, integration between the different environments.

Cloud Readiness Assessment Tools

Cloud readiness assessment tools serve as useful counterparts to a comprehensive checklist. Some of the tools TierPoint uses with clients to evaluate cloud readiness include:

  • Azure Migrate: This tool by Microsoft Azure explores and assesses your on-premises resources and offers an easy interface for end-to-end tracking and insights. It also includes insight into Azure cost optimization opportunities.
  • AWS Assessment Tool: AWS offers a prescriptive model that grants insight into where an organization is at in its cloud journey, discovers gaps, and identifies strengths and weaknesses.
  • Cloudockit: Cloudockit is a documentation tool that generates technical documentation and architecture diagrams so organizations can better visualize their cloud environments.
  • Cloudscape: Cloudscape allows for open-source development of web applications.

Cloud Migration Assessment

Going beyond a cloud readiness assessment, a cloud migration assessment serves as the first step for organizations on their way to cloud migration, and timing is critical. This assessment provides greater detail into determining what should stay, what should move, and how much needs to be changed for each application, which brings us to the 7 R’s.

7 R’s of Cloud Migration

If done right, a successful cloud migration strategy will abide by the 7 R’s: Refactor, replatform, repurchase, rehost, relocate, retain, and retire.

  • Refactor: Refactoring, or re-architecting, involves moving and modifying application architecture in a way that capitalizes on features and abilities that are native to the cloud. Doing this can improve performance, enable scalability, and boost agility.
  • Replatform: Replatforming also involves moving an application to the cloud, but the lift in the cloud is less than refactoring – some optimizing will be done but it won’t include a full modification.
  • Repurchase: Move from purchasing one tool to another that works better in the cloud.
  • Rehost: Without changing anything, move an application to the cloud for the benefits of cloud capabilities.
  • Relocate: Infrastructure can be relocated to the cloud without making too many changes, like purchasing new hardware, changing operations, or adapting applications.
  • Retain: Some applications may need to stay in their current environment because the refactoring that needs to be done is too burdensome for the time being. There also might not be a good business reason for moving a legacy application.
  • Retire: Applications that are no longer needed in either your current or future environment can be removed, or “retired.”

How We Can Help You Plan Your Move With TierPoint’s Cloud Assessment

Planning a seamless cloud migration to just one environment can involve a lot of moving parts, and that doesn’t even take into account the complexity that can come with hybrid and multicloud strategies. Managing cloud services and providers holistically, instead of viewing them as stand-alone purchases, is essential. The best way to plan your move to the cloud is with the right cloud assessment tools.

TierPoint’s Cloud Readiness Assessment can help you see the state of your services and environments as they currently stand and define a transition plan that will get you on the road to a cloud enabled digital transformation without too many pit stops or potholes along the way.

Learn more about our Cloud Readiness Assessment here.

Get your cloud readiness assessment today.

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