First, follow Stephen Covey’s unintentional Cloud Migration advice

Stephen Covey, in his 1989 bestselling book The 7 Habits of Highly Effective People, lists “Begin with the end in mind” as the second habit. But in the event you’re considering a cloud migration for your organization, Covey’s second habit should be your first.
Yes, you must first fully understand the desired end results for moving to the cloud before you do so. Whether it’s cost savings, greater flexibility, more robust disaster recovery options, better collaboration options, work-from-anywhere options, automatic software and security updates, enhanced competitiveness in the marketplace, and better, safer controls over proprietary information and documentation, you need to ensure the precise goals are outlined and communicated so everybody in your organization understands the “end in mind.” There needs to be a carefully considered reason prior to your journey. You don’t get in the car and start driving without knowing where you want to go; why would you do it on your cloud journey?
Prior to any cloud migration, you must do exactly what you would prior to any other type of journey―go through your “To-Do” checklist. Without this level of scrutiny, your cloud migration will gloss over, if not totally exclude, key elements that need to be considered ahead of time. But not checking off necessary considerations prior to a cloud migration will be far more defeating than not packing your favorite pillow or a toothbrush. Trying to correct problems from a poorly planned cloud migration can cost considerable time, expense and credibility.
The following will give you an idea of the key questions that must be asked, and carefully considered and answered, prior to beginning your organization’s cloud journey.

What’s your Cloud Approach?

Will you be utilizing a public or private cloud model, or a combination (hybrid) of the two (2)? Will you maintain certain apps on-premises or in a data center, and be using more of a Hybrid IT approach? The answer to these questions involves several key elements, including, to name a few, existing licenses, architectures and transaction volume. And considering the “6 R’s” regarding Cloud migrations will greatly assist in helping you develop the right Cloud Approach:

Remove

Empirically speaking, it’s not uncommon for organizations to discover that as much as 20-30% of their current applications aren’t being utilized and are prime candidates for total shut down.

Retain

Determine which applications should remain managed on-prem. For instance, certain latency- or performance-sensitive applications, or any that involve sensitive and/or industry-regulated data, might not be right for the cloud. There are several applications that are simply not supported to run in the cloud, and some require specific types of servers or computing resources.

Re-platform

Which applications will benefit by moving to, once migrated to the Cloud, a different platform to save time and hassles related to database management. Amazon Relational Data Service (Amazon RDS) is a database-as-a-service (DBaaS) that makes setting up, operating and scaling relational databases in the cloud much easier.

Re-host

Often referred to as “lift and shift”), moving certain applications to the Cloud can often more easily be accomplished with existing automation tools, such as AWS’s VM Import/Export).

Re-purchase

Which current applications can be replaced and utilized in the Cloud (SaaS)?

Refactor

If scaling, enhanced performance, or adding new features can be accomplished via a Cloud Migration, they might need to be re-factored or -architected.

What’s the Prioritization Order of Applications that will be Migrated?

It probably won’t come as a surprise to hear that the least critical applications should be migrated first. Start with applications that won’t leave your entire organization hamstrung if down or inaccessible, and work up from there. Subsequent, more critical application migrations will benefit from the prior experience(s).

Are Security Concerns being considered?

Think about each of the network security demands and policies that must be closely monitored and adhered to. How will they be affected from a cloud migration? Think about any industry-related requirements, such as HIPAA, PCI and those mandated by FERC or the FTC? As data migrates to the public cloud, so changes in governance strategies will probably need to be addressed.

Are the Needed Cloud Migration Skillsets on staff?

Trying to retrofit existing IT personnel with a slew of quick-study certifications will leave one important element out of the equation―experience. Think of it this way; you can read a book about swimming, but it doesn’t really mean much until you get in the water. So, if your staff has only read about cloud migrations, you’ll probably want to turn to somebody who’s been in the cloud migration water for years. And doing so will help educate your staff, even provide them with the confidence to test new approaches.

Have costs been carefully considered?

Ask IT personnel why they’re moving to the cloud, and if “to save costs” isn’t mentioned first, it soon will be. Yes, moving to the cloud can save considerable costs (if done correctly), but no two (2) environments are alike when it comes to the degree of savings moving them to the cloud will deliver. In fact, some legacy applications might cost more if moved to the cloud. And additional bandwidth and associated costs must be taken into consideration, as well. Also, make sure you understand how licensing for each application is structured, and whether the licensing is portable if moved to the cloud.

Call on the experts

Moving to the cloud is a big journey, and doing so could be one of the biggest in your career. The question is, “Will it be a positive or negative journey?” Turning to experienced Cloud experts like those at GDT can point your cloud migration needle in a positive direction. They hold the highest levels of Cloud certifications in the IT industry, and can be reached at AWSTeam@gdt.com. They’d love to hear from you.