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3 Tips to Build a Successful Cloud Strategy Roadmap

The decision to leverage the cloud fundamentally changes an organization’s existing operating models. Before you get started with cloud governance, you need to transition to the cloud, which is no small feat. If you want to be successful with such a big change, it's important to plan. That adoption plan is called your cloud roadmap.

What is a cloud adoption roadmap?

A cloud adoption roadmap documents your organization's cloud transition strategy and goals. It includes every step, action item, and deliverable of the cloud adoption journey, from evaluating cloud provider options, to implementing a migration, to continuously optimizing your organization's use of cloud technologies.

Why do you need a roadmap when transitioning to the cloud?

There are a number of considerations to consider when transitioning to the cloud beyond creating a roadmap, but trying to transition to the cloud without a detailed roadmap at minimum, ensures failure.  Most people don’t know where to start or ever go beyond the basic IT considerations when they make their cloud adoption plan. Investing more time to create a cloud adoption plan upfront, will reduce complications and make the transition easier. Here are my top three tips for creating a successful cloud adoption strategy and roadmap: determine how why and what you want to transition to the cloud, consult the right people, and make a physical adoption plan instead of just talking about it.

1. Answer the important questions.

The best way to begin building a cloud roadmap is to start with the "why." Why are we doing this? What are the benefits? Why should the rest of the organization disrupt what they're doing and buy into a cloud vision? All of these questions are important and will inform your decisions.

It should also include the "how." This, of course, includes the technical factors:

  • How are we going to move workloads to the cloud?
  • How are we going to operate in a hybrid environment?
  • Are we taking a refactoring approach or a lift-and-shift approach?

The "how" also includes cultural factors, like "how do we position people for success?" The importance of the cultural aspects should not be underestimated! Technology is often the easier part of a cloud transformation because changing the workflow of a large group of people presents a lot of challenges. How you shepherd your people along in the cloud journey can make or break your transition. Empathy, professional development, and support are just as important in your success as choosing between serverless and EC2.

As Raj Patel, the Head of Cloud Engineering at Pinterest, puts it in Case Studies In Cloud Migration, "any time you do a cloud migration-- especially with engineers-- there's always this notion of: 'Here's my way of doing it, here's your way of doing it: What's the right way of doing it?' If you had an outside group tell you this is the only way you're going to do it, you're going to run into a lot of friction."

You also need to include the "what," such as:

  • What workloads will be moved?
  • What are we comfortable moving?
  • What technologies do we want to leverage?

Finally, you need to define success. Success could be when you shut down data centers, or when all new development happens in the cloud. To define success, ask yourself what the end goal is for your organization.

Take the time to answer these important questions before you move ahead.

2. Consult the right people.

Besides getting your engineers on board, you’ll want to consult both technical leadership and people leadership to help ensure a good technical fit and help with organizational buy-in. Technical leadership representation should go beyond the director of architecture, to include roles like the principal engineer who knows the systems inside and out.

Because a cloud journey is such a big undertaking, your business leadership needs to be included. Getting the CEO and CFO on board early is important; without their support, the endeavor will be an uphill battle from the beginning. Security experts such as the CISO should also be involved once a vision for your cloud journey begins to take shape.

As GitLab writes in their Cloud Adoption Roadmap article, "the implementation phase usually requires multiple steps and thrives when teams are able to communicate and collaborate with each other. As plans change (and they inevitably will), high visibility ensures teams can adapt." Make sure that you involve the right people and you'll be on your way to a solid roadmap.

3. Make an actual map and review it often.

I recommend creating an actual cloud adoption roadmap that breaks your cloud migration down into digestible pieces and establishes a timeline. Roadmunk provides great resources for easily tackling the roadmap, allowing you to develop a plan with task ownership, milestones, and more, either as a timeline or organized by agile-friendly categories like themes, team, or status.

Free Cloud Adoption Template:
cloud strategy roadmap template

What happens once you have a cloud adoption plan in place?

Once you have your cloud adoption roadmap, you need to plan to review it often. Having a regularly scheduled cadence--say, quarterly--allows you to revisit your plans in a structure that is less reactionary than questioning the roadmap with every challenge that arises. As the organization gains more experience with the cloud, certain assumptions made at the beginning of planning need to be revisited. It's also important to revisit the roadmap to be able to measure progress against the organizational vision.

And don’t be afraid to make changes! The number one mistake I've seen is sticking dogmatically to your initial cloud roadmap. Realities change. You may lose or gain key contributors, company ownership or leadership can change, things can be harder or easier than anticipated, and of course, cloud technology changes rapidly. All of these can impact a cloud roadmap. Rigidly sticking to the original plan and refusing to adapt to change is a common mistake that can lead to failure, so be flexible about your plan.

As you draft and implement your roadmap, cloud enablement solutions will likely be a part of your technology stack. A cloud governance solution, in particular, will give you a strong foundation on which to build ongoing management and operations. Contact our team to discuss how cloudtamer.io can power your cloud governance.


About the author: Chris leads design and engineering at cloudtamer.io.