13 Cloud Readiness Assessment Tips To Guide Your Migration Success (Updated)

going to the cloud

Planning your migration to the cloud?

If you’re planning to move your organization’s applications to the cloud I suggest you take a moment and consider this important question.

What is your cloud readiness?

Let me explain what I’m asking.

To start, you just don’t go to the cloud. This phrase may sound good for cloud advertisements but it is far from the reality.

In fact, if you haven’t started analyzing your cloud readiness and flattening out your application stacks months or even years ago you may not be going to the cloud any time soon. Or on the other-hand, you may already be in the cloud and just don’t know it.

Loosely Coupled Apps

Let’s take for example applications for human resources.

Chances are these applications are very loosely coupled to any of your key business applications and therefore could score high on a cloud readiness assessment.

In fact, your HR application may already be in the cloud running as software as a service (SaaS).  And there may be other applications like payroll that are also low hanging fruit; and because SaaS is actually the cloud, these are considered wins.

Highly Complex and Integrated Apps

Whereas you may have other applications that are key to running your organization that are highly complex and integrated into every crack and crevice of your operation:

  • finance
  • sales
  • marketing
  • email

These types of applications would score terrible on a cloud readiness assessment because they have too many dependencies for data from other applications.

In fact, once you start assessing your readiness you may find apps having 3 to 4 layers of dependencies on other applications.

Think Lego Blocks versus Play-Doh!

Imagine how Lego Blocks connect together and then easily pull apart. Now consider taking 2 or 3 colors of Play-Doh and putting them together. Now imagine pulling the colors apart. Not so easy, right!

Decoupling Complex Apps

At this point getting to the cloud becomes frustrating because something everyone has made sound so easy has become a lifetime project to unravel all the complexity that has grown over the years.

Who knew 10 to 15 years ago you would be moving applications running perfectly fine in your data center into data centers hosted across the country by Amazon, Google, or Microsoft? Or that robots and deep learning frameworks would be as common as they are today, right?

The bright side of the problem is probably all your competitors are facing the same problems figuring out how to decouple their apps, too…

Cloud Readiness Begins Now!

In this two part cloud readiness questionnaire designed to help prepare you mindset for creating a cloud strategy, I will cover questions you should ask and risks (gotchas).


There are no shortcuts for doing a cloud readiness assessment.

Even with tools that can map out applications I’ve found there are always hidden connections or integration points that are missed and cause a outages when apps are cut-over from Prem to the cloud.

This is why it will take careful analysis and planning to evaluate each application being considered for the cloud.

Part #1 – Question to Ask during you Cloud Assessment

Important questions to ask during your cloud assessment:

  1. Will you use IaaS, PaaS, or SaaS or all (Hybrid)?
  2. What applications or workloads can we virtualize in advance?
  3. What servers can be virtualized in advance? (Can you P2V?)
  4. Can my current network handle the bandwidth needs if my cloud need to be hybrid? This is when services in the cloud get data from Prem services and visa-versa.
  5. What access-management will be required? (LDAP, ADFS, 3rd party)
  6. Do you have the right people and expertise? (Restful/SOAP API scripting-gurus)
  7. Which applications will need special care because of big or complex databases that use a lot of storage?
  8. Which cloud provider is the better model for my type of workloads? (Google, AWS, Azure)
  9. Which cloud provider is going to offer best enterprise support when thing start getting difficult?

These are just some of the questions you want to answer during your cloud readiness assessment.

The best time to begin your cloud assessment is Today!

Helpful Video about How To Create a Cloud Readiness Assessment

Cloud Fever

You’re not alone.

The movement towards the cloud has been building momentum and it’s increasing pressure on top leadership to fall in-line.

cloud study showed that 50% of the companies were expected to move to the public cloud by 2015, and that number increased by 2017 as success stories are flaunted in the news.

But what’s still holding a lot of companies back are concerns about the risks they will expose their business to during and after the move. Risk alone is no longer a good enough argument to stop cloud fever…

Along with the questions I’ve provided above, here are some gotchas to look out for as you plan your cloud strategy.

Cloud Readiness Framework Video

Part #2 – Cloud Migration Risks (Gotchas)

If you decide to migrate to a cloud platform, you need to a clear strategy. In this part on cloud readiness preparation, I’ll cover 4 gotchas that could cause you problems if they’re not addressed up front during the planning phase.

Consider the following to help AVOID fires:

1. Network Impact Analysis

Shifting to cloud technology could have an adverse effect on the company’s network.

The effects on the network can include inability to access databases, applications and many other dependent services over the web or on your internal network.

Considering a Network Impact Analysis (NIA) is crucial for ensuring the company has reliable and sufficient bandwidth to support the new load.

A mistake many companies make is storing large amounts of data or files off-sight without using in-house servers. This causes excessive amount of ingress traffic and can easily overload circuits and make them unreliable.

A complete network analysis is important to avoid problems later with slow applications due to oversubscribed network circuits.

Helpful hints:

  • What is ingress? Ingress is inbound network traffic.
  • What is egress? Egress is outbound network traffic.
  • Most cloud service providers charge a fee for both.

2. Technical Support Agreement

Technical challenges are likely to occur that will challenge your internal IT staff. A reputable cloud provider should be able to help you solve your problem without too much fuss.

A service level agreement (SLA) will help you to understand who takes responsibility for the faults and how fast they should be fixed if they occur.

You should bear in mind that the SLA should be unique to what you’re requirements are and the fees you are willing to pay.

3. Security! Security! Security!

The number one concern for most businesses considering public cloud services is security, especially in today’s highly sophisticated world of Phishing and Ransomware.

It’s important to know who will be responsible for security, especially where confidential or sensitive data such as PII or PCI is concerned.

It’s incredibly important that you know going into the cloud that your company will likely own the responsibly of protecting you data from security breaches.

Most cloud service providers prefer leaving security to their customer and don’t want the liability.

Cloud security is a very sensitive issue that needs to covered from end to end [data, devices, and applications].

The security agreement should also cover compliance and governance issues, which should also be sector or industry specific.

Check to ensure the provider you’re considering has a security policy suitable to your business and validate it’s compliant within the laws of your state. Read more about cloud security concerns.

4. Cloud Expertise

If you don’t already have IT staff with cloud training, your cloud provider should have technical expertise on staff with industry accreditation, and a lot of experience in the cloud migrations.

Look for service providers who have worked with similar companies like yours because they will know what works and what doesn’t work.

Check references and speak to other clients before deciding.

There’s definitely a lot for you to think about if you decide to shift your company IT infrastructure to the cloud and cloud expertise should be near the top of the list.

Have experienced cloud engineers do a deep dive that takes you through network security and design, all the way to implementation of the project and maintenance.

An experienced partner will help you identify aspects that you never thought about and they should also be able to pull the plug if the complexity is to great for success.

You don’t want to get a quarter of the way there and have to roll back because you ignored the data.

Free Cloud Readiness Checklist Video

Get the most out of the Cloud!

In summary we covered questions to ask and risks to consider. But this is only high level food for thought before you move forward and actually discover what benefits you’ll find by going to the cloud.

One final word of caution:

Be prepared because it’s very easy for things to get out of control with the point, click, and deploy most cloud portals use to self-serve their customer over the Internet.

With a trial account someone could start deploying servers or services in minutes without considering the risks or costs we have discussed above. I recommend reading more topics about the cloud before beginning your journey. Good Luck!

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