Migrating data solutions to the cloud: a checklist Part 1 of 9

If you are a follower of me in the various places or a reader of this blog, you know that recently I presented the session Migrating data solutions to the cloud: a checklist at SQLBits 2023. As promised in the weekly wrap-up from April 7th, here is the first installment of a more in depth dive to that session. The session had 9 parts to it and so I thought that would make for nice chunks to consume in blog posts. I’ll add links to each one so it will be easy to navigate once all of the posts are up.

The Parts are broken down as follows:

  1. Pre-Planning and Evaluation
  2. Discovery
  3. Assess
  4. Architecture
  5. Costs
  6. Migrate
  7. Testing
  8. Post – Migration
  9. Resources and Closing

This post will focus on the first item in the list Pre-Planning and Evaluation.

Let’s get right to it! Ok ok. I know you are probably chomping at the bit wanting to immediately get into the technical parts – I know how it goes – but that is not where you start.

King from Alice;s Adventures in Wonderland

“Begin at the beginning,” the King said, very gravely, “and go on till you come to the end: then stop.”

― Lewis Carroll, Alice’s Adventures in Wonderland


What is your company’s goal of moving to the cloud?  Some examples are:

  •   Reduction in CapEx (capital expenditures)  
  • Lower reliance of complex and/or end-of-support technologies
  • Optimization of internal operations
  • Reduction in vendor or technical complexity
  • Preparation for new technical capabilities

Modernization? Cost-savings? Multiple things? Maybe your current infrastructure is at end-of-life, and it just really makes sense to modernize it and move it over to the cloud before you are dead in the water. Or maybe your goal is to reduce downtime for managing infrastructure and upgrades .

What is the problem you are trying to solve? Is there a business requirement driving this or maybe something else? Make sure you understand what the problems are you are trying to solve and if your goals actually address those problems. That is a business decision that has to be determined WITH your technical team and not necessarily BY your technical team. I’m a technical person, and I’m going to be the first person drawn by the shiny new object – which often is not the best thing for the company strategy.

Image matching goals to problems trying to solve.

Ultimately your problems can drive a portion of your goals, but you may have additional objectives. These items need to be determined upfront so the choices you make during the process align. They create value streams for your organization. Higher ups love to hear about value streams!

Once you have your objectives – you can create a plan and KPIs towards those objectives and then show how you met those at the end. This is our objective, this is the state at the beginning, this is the state at the end. Look how far we’ve come!!!

It’s hard to have project success if you don’t define what your objectives are. This is a project, and if you’ve been working on projects for a while, you know how easy it is to go sideways and lose sight of your goals. Sometimes those goals change a bit, and that’s ok, but ultimately your success will be measured by if you achieve clearly defined goals that you can apply metrics towards.


Blocks that contain the text "Executive Support" and "Stakeholder buy-in".

Executive Support

Many times, you will go into a migration project that is being driven by the top level. Maybe your CEO went to a conference or read some important articles – and if so, you are ahead of the game (well, until you have to set expectations properly). But if you don’t already have executive support, then you need to identify an executive sponsor. Someone who is high up and can lead a cultural shift within your organization. A Champion. <insert bugle sounds here>

Stakeholder Buy In.

You need to Identify and involve key stakeholders early in the process. On both the business and IT side. Involvement and communication is key.

People don’t like change. Try telling a bunch of financial analysts that have been doing their job for over 20 years and have lived through multiple technology shifts – try telling them they won’t have Excel anymore. I promise you; it won’t be pretty. Rather than focus on what you are taking away – focus on why the change is needed, and what it gives them. How can you get their buy-in for your project, while still being honest.

If you don’t have that executive support or stakeholder support, then you may need to a little digging. What are your company’s core values? What is the 5- and 10-year plan for business initiatives? How does moving to the cloud address these?  At the department level – what are primary goals and concerns from a technical perspective. How can moving to the cloud help this? Everyone’s answer will not be the same but look at how you can align key stakeholder needs with the goals of the C-Suite. Building a business case that addresses top concerns and how the cloud will help – is ideal for this situation.


The next thing we need to consider is what we will do in-house versus what we may pull in a partner for.

Internal Team:
-Determine SME Req
-Identify key members
-Assign roles
-Assess skills

For your internal team – first determine the different areas you will need a SME (subject matter expert) for, and a good idea of what they need to know. Second, identify potential key people you may have in-house to fulfill these roles. Ideally you will have people in your organization from across many teams  that you can assign to roles. Once you have assigned roles to people, you need to assess their skills. This will allow you to see what gaps you need to fill and then plan for how your org will both fill and monitor those domain gaps?

When possible, identify potential team members that either have the skills or can upskill. Build a skills readiness plan. Investing in your people is far cheaper than hiring outside help. Consultants are great – I know, I’ve been one, but there is no replacement for having in-house knowledge, particularly once those consultants have finished and walked out the door – potentially without much knowledge transfer. The people that will be maintaining and growing your systems need to have the skills.

That said, in some cases, you may want to hire outside help. Maybe many of your team members are really spread thin, or the upskill process doesn’t match the timeline – then definitely bring in consultants.

Common things for partners to be involved in:

  • Strategy: Help with defining all things such as business strategy, business cases, and technology strategies
  • Plan: Help with discovery tasks, such as assessment of the digital estate and development of a cloud adoption plan.
  • Ready: Support with landing zone tasks.
  • Migrate: Support or execute all direct migration tasks
  • Innovate: Support changes in architecture
  • Govern: Assist with tasks related to governance
  • Manage: Help with ongoing management of post-migration tasks

Along the lines of consultants – help them help you. Does your company have standards or best practices that are specific to your industry or workflow? Share that with them. Share any and all documentation that is relevant to your migration and environment.

If your company is able – consider Creating a board for key team members to interact and meet regularly: like a Cloud Center of Excellence (CCoE). Key members are chosen from each  IT areas to meet at a specified cadence to discuss all things Azure including identifying domain gaps. Those key members not only gain knowledge about technical aspects, but also get insight into projects that are going on through the different areas of the company. And they can take back that information to their team with a level of consistency. Which is super important when you are wanting establish best practices and standardize policies across teams.


Now we need to find out what we have regarding documentation.

From the technical side you need to assess at what your current infrastructure looks like. What type of documentation do you have for your data estate and infrastructure?? Where is your data? What does your data require for things like storage and memory? What are all the components that connect to what you want to move? If you don’t know what your current infrastructure looks like, you need to determine how and who will document that for you.

On the business side: What are business requirements for your systems?  Do you have regulatory requirements? SLAs mandating certain uptimes? What about other Business requirement docs for security, compliance, backup, Recovery Point Objectives (RPO) and Recovery Time Objectives (RTO)?

And finally – have you previously tried to do a cloud migration? What documentation is left over from that? Is it current? What were some of the successes and some of the failures? Any lessons learned?

You don’t have to know everything at this point, but you do need to find out what you have and what you don’t have. And if we are perfectly honest – what may be out-of-date. This is where you need an Enterprise Architect and some in-depth meetings with the different departments. Communication is key to getting the documentation and finding what you have, what you don’t have, and what you may need down the line.

Welp, that concludes Part 1: Pre-Planning and Evaluation. What would you add to this list? Have I missed any additional parts that you’d like to see in the over all series? I love to get feedback to consider so feel free to reach out.

Stay tunned for Part 2: Discovery.

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