Enterprises are moving their databases and data warehouses to the cloud for all kinds of reasons: reducing costs, staying competitive, being more agile and innovative, taking advantage of new features, and replacing capital expenditure with operational expenditure, to name a few. They all have one thing in common – the belief that the cloud is a much better option than expensive, high-maintenance, on-premise data warehousing solutions. Maybe, you’re just starting out on your journey to the cloud, or maybe your replatforming project is already underway. Either way, this cloud migration checklist should help you be aware of the challenges you’re likely to face, how to prepare for them, and how to reduce the risk and cost typically associated with database replatforming.

By the way, Gartner estimates that at least 60% of replatforming projects will fail, go over budget, or run late. This is largely in part due to the database migration paradox: moving data to the cloud is surprisingly easy but getting applications to work with the new cloud database is incredibly difficult. The most common approach to replatforming is to completely rewrite applications, which is as painful and time-consuming as it sounds.

Large enterprises frequently embark on application rewrite projects that take up to five years (often more) and cost tens-of-millions of dollars. Being properly prepared can make a big difference and ensure that your journey to the cloud is a smooth and worthwhile ride.

Before setting off on the path to the cloud, make sure you have the answers to the following five questions:

1. Why are you moving your database to the cloud?

Make sure you know why you’re migrating to the cloud and keep your eyes on the prize when planning your replatforming project.

Common reasons include an executive mandate, the need to reduce costs related to your current on-premise database solutions, taking advantage of new features offered by the cloud provider, needing more storage or computing power, and needing increased agility to innovate and stay competitive.

2. What kind of timeline are you willing to set for a replatforming project?

Typically, rewriting applications takes several years, assuming it goes off without a hitch. It helps to break the project into phases and define specific goals: for example, getting the enterprise to 80/20 cloud/on-premise goal by 2020.

Using emerging technologies, such as virtualization, can potentially lead to a much shorter timeline.

3. Who is the right cloud provider for your enterprise?

The big public players – namely Amazon and Microsoft, along with other players like Pivotal and Google BigQuery – have different pros and cons to their offerings. You might also be looking at hybrid cloud or private cloud destinations.

Here are some useful questions to ask while evaluating cloud providers:

• What is your staff’s experience with each vendor?
• Does your team already have the required skillset, or would you need to hire new talent to fill the gaps?
• Do you want to build a solution from basic blocks for a more custom outcome, or take a more simplistic approach with a turnkey solution?
• How important is the maturity of the cloud provider’s offering?
• Have you done an evaluation with a system integrator to help determine the best option?

Answering the questions above ahead of time will help ensure that you have everything you need when the migration is complete.

4. How many of your existing database or data warehouse workloads are compatible with the cloud?

When planning your project, it’s important to pay attention to what work will need to be done before you start, and what is already supported by the destination cloud data warehouse system.

Important questions to ask when determining this:

• Did you account for missing features?
• Do you have old operating systems in the mix, like AIX, Windows 2003, etc.?
• Do you have old versions of software that will need to be updated first in order to be compatible with your cloud destination?
• How are you going to generate a schema for the new data warehouse?

Typically, rewriting applications takes several years, assuming it goes off without a hitch. It helps to break the project into phases and define specific goals.

5. How are you going to make sure your existing applications work with the target cloud data warehouse?

This is the most challenging part of the process, and it’s important to know what method, or combination of methods, you’re going to use to get the job done.

Here are some questions to consider:

• Are you going to fully rewrite applications if they are not compatible with the new system?
• Are you going to make use of emerging virtualization technologies to simplify the process?
• Will you lift and shift your applications?
• Repurchase your applications, where applicable?

In conclusion, moving from an on-premise data warehousing solution to a cloud-native solution can be a daunting task, but the explosive increase in revenue reported by leading cloud service providers is evidence that the journey is worthwhile for the enterprise. In fact, this survey found that 77% of the respondents said their organizations were planning to move to the cloud within the next two years.

When your business decides it’s time to make the leap, make sure you can answer all of these questions with confidence – because knowing your workloads and having a plan are key to a successful journey to the cloud.