9 overlooked steps to create a successful cloud migration strategy

1. Define the goal of your cloud migration strategy

2. Audit your system documentation

3. Optimize your systems for a cloud migration

4. Update monitoring processes

5. Update cybersecurity practices 

6. Train and retool your team

7. Calculate your cloud migration outage tolerance

8. Read the fine print in your cloud provider agreements

9. Optimize your backup solution for cloud

Leaders who complete a successful cloud migration strategy starts with a different goal. To them, the end goal is to move their technology-related resources into a model that’s easier to manage and drive larger business outcomes. Without that goal, you're migrating to the cloud just to migrate, which may cost you more in the long run.

But the more comfortable you become with cloud technology, the more value you can drive. For some, that looks like adding more infrastructure to the cloud. For others, it's defaulting to cloud solutions or going multicloud. But as long as you keep your sights set on driving those business outcomes, you're on track for a successful cloud migration.

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One mark of a successful cloud migration strategy is how quickly users get back to business as usual. Complete and accurate system documentation makes that possible. Before you start thinking about a cloud migration, go through your documentation. Do you have current documentation processes, usage models and dependencies? If not, you could be putting the success of your cloud migration at risk.

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Best practice is to review all your applications to ensure the architecture is already optimized for cloud. If it needs modification, build those changes into your cloud migration strategy. Most newer systems are already optimized for cloud migration and can migrate easily. 

Be wary, though, even some cloud-friendly systems create unaffordable technical debt. A successful cloud migration strategy isn’t only about getting your systems to the cloud. Migrating your systems as is does you no good unless they’re optimized for cloud hosting and cloud’s benefits.

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Cloud migrations require a fundamental change in operations to reap the long term rewards. You need to know what's going on in your applications at any given time. That means being able to measure performance and health. You need a monitoring framework that’s application-focused and able to perform health checks for an application that, at any moment, may be on different nodes than moments before.

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As with monitoring frameworks, you need to ensure your application can be secured before your cloud migration. Most security tooling uses IP addresses or host names to enforce or manage an application’s security. But applications on the cloud don’t have a static IP address or host name. Instead, they need to be programmatically set using dynamically provisioned and updated values.

But that’s just the beginning. You also need to change your security practices for updates, patches and upgrades. Cloud security operations are completely different from on-prem security operations. For example, you shouldn’t ever patch a server in the public cloud. These VMs are short-lived and can fail, unlike on-prem servers which can be leased for years at a time.

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After you successfully migrate to the cloud, the way your team interacts with your tech stack changes. Instead of training them to remotely log into a server or network device, train your team to initiate scripts that run the whole process for them. That also means re-training them to build these scripts and use code repositories to automate simple tasks.

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And then there’s the business cost to a cloud migration. Teams that perform a successful cloud migration use their outage tolerance—the amount of time your business can be down without critical business repercussions—to design their cloud migration strategy. They put organizational needs first. For some teams, it’s better to perform several cloud migrations requiring shorter downtime than a single cloud migration.

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Once you know which cloud, or clouds, you’re planning to migrate your data to, go through all your existing contracts with a fine tooth comb. There are many things that influence a timely and successful cloud migration like licensing requirements, time-dependency requirements, and versioning.

Licenses may not be supported in the cloud, or may require compliance systems to validate total license counts. Some software vendors require changes to contract terms for cloud-supported licensing. The most common licensing headache, though, is preparing for migration. 

You should check to see if your licenses can run in both the cloud and on-premise during your migration period. If they can’t, you’ll need to change your cloud migration strategy or prepare to pay for double the licenses while your team completes the successful cloud migration.

Some vendors enforce time-dependent rules. So if you move software to the cloud, it has to stay there for a set time period before you can move it again without penalty. Most often, the penalty is having to pay for double the licenses.

While you’re looking at contracts, double check that you’re running the latest version of each software application. Older versions may not support cloud migration, and you'll need to update them prior to migrating.

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The most overlooked piece of a successful cloud migration strategy is a data backup process. Not all data backup tools and processes support cloud-based data retrieval and storage. Data recovery and retrieval processes protect you from ransomware and other malware attacks. 

But there are also legal ramifications for not verifying that your data backup process is in place and accurately backing up your data. In addition to making sure new data is backed up once your systems are migrated to the cloud, you also need a way to retrieve current archived data.

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