How I approach the discussion

When I begin a discussion on migration to Azure with an organization, it is a bit different than a greenfield discussion because we have something in our hands. We know the size, shape, and history of the application we are moving. Let’s look at things we should do in this scenario.

We want to start by assessing the applications and infrastructure, and we do this in the following way:

• Discovery, which allows us to peek under the hood of the applications and infrastructure needed to support them. This is not only the code but such things as DNS and services needed to support the application. This is helpful, as not every application is a good candidate to migrate or you may need to secure VPN connect to the internal resources that can’t be moved to Azure.
• This will lead to mapping your applications to discover all dependencies, which to me is the best exercise as every single organization I have consult with discovered something new with this process.
• Once you have all this together, you can evaluate which applications make good candidates to move to Azure and which ones need to be modernized.

Once you have gathered this information, you will have some choices to make and it is good to get into those uncomfortable conversations within the organization so as to fit your applications into one of the following buckets:

• Rehost
• Refactor
• Re-architect
• Rewrite

Let’s take a deeper look into what these mean and how each has its own merits depending on the state of your application and discovery.