Cloud Migration Series (Step 2 of 5): Start Planning

Cloud Migration Series (Step 1 of 5): Define Your Strategy

This is part 2 of a 5-part series on best practices for enterprise cloud migration. Released weekly from the end of April to the end of May 2021, each article will cover a new phase of a business’s transition to the cloud, what to be on the lookout for, and how to ensure the journey is a success.

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Start planning your cloud migration

You’ve defined your cloud strategy. You understand why you want to take a journey to the cloud. Now that the high-level strategy is done, let’s focus on the nitty-gritty and the details. It’s time to make a plan for making the big change. Don’t get discouraged, as it’s going to be a lot of work. That’s why we’ve created this series to help you.

Budget for the journey

You’re going to have to sit down and have a realistic conversation with your technical leads and executives about how much a cloud migration is going to cost. Let’s be clear, a migration from legacy systems is not like flipping a switch, nor is it a one-time affair. Rather, like most change that lasts, it’s a process with milestones. 

As you go through the continuum of change, you’ll eventually leave some or all of your legacy systems behind (depending on your views on hybrid cloud). But as that is happening, you’ll need to maintain old systems, scale new systems, and make sure you have the right employee talent to keep things progressing forward. 

A few key facets to consider:

  • Current budget and fiscal year considerations
  • Ideal timeframe for transition
  • Product roadmap, short- and long-term

Check your infrastructure

Before you dive in and take the whole organization with you, let’s take a look at what’s being developed in the various groups in your business. Some of these might be more translatable to the cloud, such as lightweight mobile apps. But remember, there are so many cool technologies and buzzwords out there (Kubernetes, agile, data lakes, real-time everything) — you have to think hard about whether there’s really a business case to jumping in. 

For example, maybe you run a monolithic app that’s been your bread and butter for years. Maybe it’s worth it to host the app in the cloud, but not change to microservices. Instead, since you’ve taken a good look at your product roadmap you might spin off a new product that can then benefit from some quick cloud-based solutions, such as turnkey managed services like AI libraries or data analysis.

Initial organizational alignment

The last thing you want is for people to leave meetings about your migration and have nothing happen. Fast forward six months and progress has been scattershot, not much morale, and zero inertia. But let’s not focus on the negative…what are actionable steps to take to guarantee forward movement?

In part one we talked about organizational buy-in. A good way to maintain internal accountability is to create a multi-disciplinary “Tiger Team” — a group of individuals who can meet to maintain focus and ensure that separate groups don’t become too siloed.

Modify this to your own needs and don’t bog people down with fluff, but do hold them accountable, whether it’s by unintrusive meetings or reports to leadership. Remember, this effort has to be supported from above, as a positive culture starting from the top can be contagious. 

Assess your team

How are you going to get your team from point A to point B? Will they be ready to not just take steps toward a migration, but toward creating products in a new way?

Your product, engineering, and IT teams are experienced in designing, creating, testing, and deploying monolithic applications. They probably have some experience in cloud technology already, and it’s more than certain that they have a deep curiosity to learn more: that’s part of the creator’s mindset and that’s why they’re in this field.

Now you need to establish a baseline for where their skills are, how that aligns with your strategy and planning, and how to raise their skills to meet your strategy.

Develop a skills readiness plan

If you want to create an effective plan for your employees’ technical growth, you need a good way to assess their skills and develop them at scale. We’ll review this more in part three of this series, but here’s an overview of how it’s done.

Start by accurately pinpointing baseline skills

  • Test competence across multiple cloud platforms and technologies and track skill improvement
  • Test practical, hands-on tech skills
  • Streamline the assessment process with automated reminders
  • Understand where your team stands and how fast they’re growing

Quickly increase technical capabilities

  • Drive skill growth with hands-on cloud training programs built to master AWS, Azure, Google Cloud, DevOps
  • Build and assign training plans with 10,000+ hours of up-to-date cloud training
  • Keep your team accountable with built-in reminders and weekly reports
  • Track progress and completion on a real-time dashboard

Confidently know when your team is ready

  • Measure practical expertise through skill reports based on hands-on assessments.
  • Challenge your team with lab scenarios using actual AWS, Azure, and Google Cloud accounts
  • Establish a data-driven approach to learning and skills management
  • Understand your team’s strengths and identify skill gaps

Cloud adoption plan

Migrating to the cloud isn’t just about technology. The mindset and the repeated, tactful reminders to stay on course help to make all the difference.

You’ll find that one of the main challenges with transformation projects is keeping a clear sense of direction. Often with a transformation project, there isn’t a dedicated project resource to run it. That means it’s easy for people on the ground to lose focus a bit and end up working in silos or vacuums. Confusion can set in and the wheels can quickly fall off — everyone loses interest and inertia. 

What can make a significant difference is when learning and development have a clear program structure to drive the behavioral outcomes that leadership wants to see. This can be the backbone to build your cloud adoption plan on.

On top of this framework, you can start to build the basics of how to use cloud services both securely and efficiently. Then you will layer the most important factor on top: your people. Your people will use the framework to both increase their skills and collaborate with new (and sometimes scary) tools and technologies.


Now you have a plan for how to get your arms around this whole digital transformation. Next, we’ll dig deeper into your people and how to assess readiness for your team. You’ll learn about what to look for and how to know you’re all set for your cloud migration and for whatever technical projects you choose in the future.

Ready, Set…Cloud!

If you’d like a preview of what our blog series will cover in a more in-depth fashion, this guide is a great start. We share some best practices and insights gained from our experience helping many organizations on their journey to cloud success. Use it as a helpful reminder to stay on track.

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