Cloud illustration with background of a rainforest and winding river with the caption Moving to the Cloud

Make Sure you Pack for the Trip

Let’s start with the map and the compass. Cloud journeys are, let’s say, protracted ventures. For long journeys, you need to tell everyone how you will get there, and you need a way to locate your position while on your journey. Write down the plan. The plan must include budgets, resources, and timelines. Luckily the major cloud vendors provide insightful cloud adoption frameworks, which you should follow (unless, of course, you are already experts, which you likely are not).

You should set up a cloud organization with cloud operations, a cloud center of excellence, and adoption and governance branches. You need to decide if you will lift and shift, re-platform, or discard assets. How will your new greenfield projects intermingle with your legacy migration projects? Are you completely bought into Infrastructure as Code, which implies that even the corners of your IT organization resemble a development team? You should frequently caucus, consider your path, find out where you are and adjust as needed. Be aggressive about monitoring your progress and equally open to change. It is a journey. You will figure out what works for you by doing, measuring, and adjusting.

Although … There is one thing you need to get right – your foundational landing zone. Start iterating on your landing zone as soon as possible. This is where your networks, policies, subscriptions, naming standards, and resource management lives. Everything you do builds on the landing zone. There are decisions to make, especially as a company with very sensitive data and a company that will maintain a hybrid of datacenters and the cloud. As you move workloads into the cloud, you won’t get a ton of chances to revamp the landing zone. Don’t delay.

This brings us to the journey – take the proper tools and equipment with you. I can’t stress enough that you need to understand the tools that your cloud provider offers. You must decide if you want to bring along your on-premise tools, get a new third-party set of tools or use the cloud provider’s tools. You will want to design how you will deploy, monitor, manage and secure your environment. How will you meet your SLAs? What about availability and integrity concerns? How will you monitor health and status? How do you assess and remediate vulnerabilities? You need to choose which tools you will use because, to no surprise, you still must meet your company’s operational requirements. To do so, your operations teams need the tools for a consistent, unified management view of your entire IT enterprise.

Additionally, this idea pertains to selecting platform services, such as serverless compute, container orchestration, blob storage, event management, databases, key storage, and the like. One of your most important decisions will be to determine if you want to run in multiple clouds. Do you want to lock into the cloud service provider’s native services or abstract away from those? Popular wisdom is that you will go faster using the cloud native services. If you are a single cloud outfit, then you should seize on the native services mantra, and again, tell everyone in the company that is the direction you are taking.

Now to the tricky part. How many resources do you need for this journey? I’ll guarantee you that whoever sold the strategic cloud move to the upper regions of the organization didn’t properly set expectations for the number of resources you will need. Their expectations of what it takes are probably low. It’s not intentional; it’s just life in the software industry. I know we live in an agile software world. But you had better get out in front of the resource requirements. Big projects need a plan, and resources are part of the plan. At some point (hopefully very quickly in your journey), you will need people to do the work. It’s extra work beyond what your people are currently doing. It requires people with skill and passion to swing that machete and build that road – more people than you have on staff. Lack of resources can devastate your mission. I recommend setting up an exceptional training program in the CCOE and ensure that everyone, especially those that will be working in the cloud, acquires the necessary skills.

Which brings me to expert guidance. Don’t walk into the jungle without a guide. It’s foolish. It’s called playing around and can be great fun until you get lost. You need to bring on key people to guide you. Early successes are key to transformational efforts. Guidance extends to setting the organizational structure and the culture that you want to achieve. Great people need a great environment in which to accomplish great things. The expert guidance can help you set that environment to achieve the streamlining and collaboration necessary to flip the iceberg model.

Go Forth and Do Great Things

Finally, and seemingly contrary to what I’ve said so far, don’t get paralyzed by analysis. Get started. Let it breathe. Cherish your first-in projects and the people doing them. They will tell you where the valleys, cliffs, rivers, and mountains are. But don’t get too attached to what they produce. Don’t let that first-in work become pets that you name unless you just want to stay behind taking care of a bunch of pets. Tear things down and rebuild as needed. (This points out why automation is critical to your success.)

And resist the temptation to lock everything down. We all want to have the best security, but please perform the data classification and threat modeling to arrive at the correct security in the correct environments. You can easily create protection level 4 systems way too soon that are overbearing and consequently stifle innovation and discovery. You can even baffle your cloud provider with your security cleverness. It’s nothing for which to strive. Security is absolutely critical to your business, but so are cloud playgrounds that don’t house sensitive things and limit the blast radius from mistakes. Let it breathe, learn, and then lock things down to fit your mission, development, and operations models.

When all is said, the journey to the cloud is an amazing one. If done for the right reasons, it can transform your business. When standing at the edge of the jungle, it looks to be a daunting journey. But if you plan, lead and communicate the cloud as both the big idea and the journey to realize that idea, you won’t look back.

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