Cloud Migration Series (Step 3 of 5): Assess Readiness

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

This is part 3 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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Assessing your ready state

Last time, we talked about detailed planning that forms the foundation of your cloud migration effort. Now it’s time to really understand what your team can do, and how you can help them get to a place where they’re empowered to enact a big organizational shift.

Making a big change like this is a huge undertaking when you work in a large organization. There’s little guidance out there for executive teams on just how much learning effort is required to turn the ship around. What’s needed is to have your Learning & Development team present a clear direction on the training goals — the result will go far to ensure that things go smoothly.  

Why is the buy-in from L&D important? Some of the biggest mistakes happen in the early stages of cloud adoption when enthusiasm for new tasks and appetite for experimentation is high, but knowledge of best practices is low or non-existent. In order to get into a cloud console and start doing things, your staff doesn’t necessarily need to pass a cloud certification exam before they can spin up instances. It’s easy for people to make expensive mistakes in the early stages of adoption if they don’t know or understand the proper operating procedures. L&D needs to be the first line of defense in the first stages. 

So our first goal needs to be understanding where your team stands with regard to technical skills, followed by a plan to get them to a ready state to accomplish the technical goals that you laid out in the planning phase.

Readiness is both a state and a process

You’ll start by accurately pinpointing your team’s baseline skills. Once they are on track, you’ll then want to upskill them again to make sure they stay up to date with constantly changing cloud technology.

This brings us to a main point. As you assess your team, grow their skills, and make sure they’re on track, you’ll realize that this is actually a process of continuous development. Just like agile software teams that work in sprints and constantly deploy code updates to certain parts of an app in order to stay current and update products, the readiness stage of your cloud migration is the same. It will be a culture change for your organization, one with positive impacts because your teams will be ready, and will be motivated by individual and group growth and success.

Here are some highlights of what a readiness program should entail:


To get started, you’ll need to determine your team’s current skills and capabilities. This means creating a breakdown for each individual member that can be updated as they progress through their learnings.

Skill Assessment

You don’t want to be in the dark about your team’s abilities, so you’ll need a full view in order to build on each member’s development. This helps you predictably upskill talent so you know exactly when they’re ready to tackle that new project. Useful metrics will include strengths, weaknesses, and areas of opportunity.

When you think about it, the ROI of your tech stack is only as strong as your team members operating on it. You’ll need to use the insights from multiple skill assessments to paint a picture of broader skill coverage, ideally from the individual, team, and organization level.


Yes, dashboards are all the rage and will continue to be so, for good reason. A well-designed dashboard helps you cleanly separate signals from the noise.

Ideally your dashboard to monitor organization readiness will contain the following items:

  • ability to assign assessments
  • current skill levels
  • an organization of teams that effectively mirrors your internal organization

These seem like simple things, but they often get overlooked. It’s key to focus on these tenets because while the many programs roll out in tandem, it will be easy to get overwhelmed with too much information.

Cloud-first: four key goals to keep in mind

It bears repeating that there will be a lot going on in your organization. This readiness and learning stage of a cloud migration is going to set you up for success as you adopt a cloud-first mindset. 

The new mentality at your organization will consist of the following key understandings, which will eventually become part of the healthy baseline culture.

  1. Being aware of cloud tools and services
  2. Being able to use cloud services effectively, economically, and safely
  3. Understanding how to apply cloud tools to solve customer problems
  4. Being able to use your cloud services together to create new products and solutions


This is exciting stuff — changes, new technology, opportunity for growth. In part 4 of our series, we’ll delve into maintaining that cloud-first mentality, especially when the going gets tough and real-life challenges invariably pop up to get in your way.

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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