Cloud Migration Assessment: A Practical Guide to Best Practices

Cloud migrations have become a cornerstone strategy for organizations aiming to modernize their IT infrastructure, enhance scalability, reduce costs, and drive digital transformation. However, migrating to the cloud is not without its challenges and requires a thoughtful, well-planned approach to avoid unforeseen complications and unnecessary complexity. A comprehensive cloud migration assessment helps ensure proper planning and a smooth transition to new cloud environments.

This article explores the key components of an effective cloud migration assessment, from defining clear business goals to carefully scoping an initial migration. It discusses the importance of identifying IT assets, understanding landing zone requirements, and beginning with non-critical workloads. It also discusses why maintaining the original hardware can be beneficial after migrations and how specialized tooling can significantly streamline the assessment and planning stages.

Following the best practices outlined in this article can help IT leaders and their teams navigate cloud migration with confidence while minimizing risk, so they can quickly realize the benefits of their cloud adoption strategies.

Summary of key cloud migration assessment best practices

Best practice	Description
Define the organization’s migration business goals	Assess the business justification behind the cloud migration to understand where to focus the most efforts. Common drivers include cost reduction, data center lease expirations, or hardware that is reaching the end of life.
Tightly scope the initial migration	If this is an organization’s first foray into the cloud, start small. Most employees will need time to upskill and learn new patterns, and the stress of a large migration can overwhelm teams.
Identify IT assets to migrate	Once an initial set of workloads has been defined, run infrastructure discovery software to map dependencies and create a comprehensive inventory of assets to migrate.
Select the best providers for each workload	Workloads can be placed across different cloud providers, especially if they involve specialized use cases such as Oracle databases or Microsoft SQL Server.
Define landing zone requirements	It is likely that cross-connectivity will be required between the source destination and the new cloud environment. Building a landing zone that considers hybrid networking ensures that identity and connectivity patterns will be compatible between environments.
Migrate test and development workloads first	When the migration is ready to begin, start with the smallest, lowest-risk workload first. This helps prevent unforeseen downtime or outages and allows staff to build confidence in new patterns.
Wait to decommission the original hardware	If the business allows it, formerly used hardware can be helpful for troubleshooting or fallback scenarios.

Define the organization’s migration business goals

Most cloud migrations are prompted by a change in the business. These changes may be cultural or financial, but understanding them is essential to ensure that the migration outcome aligns with the initial goals.

For example, if the cloud migration is being done to exit a data center lease prior to a pricey renewal, there are likely deadlines to consider and cost implications if the deadline is not met. On the other hand, if a cultural change is driving the decision to move to the cloud—such as a long-term plan to embrace serverless or microservices architectures—there may be more flexibility in timing and initial workload selection.

Each business stakeholder with a vested interest in the cloud migration should share the same measure of success for the migration project. Communication among stakeholders should match an organization’s existing project management process when approaching large projects.

Common business goals for cloud migrations include:

• Cost reduction and optimization
• Increased agility and scalability
• Improved security and compliance posture
• Enhanced disaster recovery and business continuity
• Acceleration of digital transformation initiatives

When defining these goals, it’s important to make them Specific, Measurable, Achievable, Relevant, and Time-bound (SMART). For instance, instead of a vague goal like “reduce costs,” a SMART goal would be “reduce infrastructure costs by 25% within 12 months of completing the cloud migration.”

SMART goal acronym visualization (source)

Additionally, establish key performance indicators (KPIs) to measure the success of your migration. These might include:

• Total cost of ownership (TCO) before and after migration
• Application performance metrics such as response times or throughput
• Uptime and availability percentages
• Time to deploy new resources or applications
• Security incident response times

By clearly defining your migration business goals and success metrics, you create a solid foundation for your cloud migration assessment and ensure that all stakeholders are aligned on the expected outcomes.

Tightly scope the initial migration

Many organizations migrate to the cloud to reduce their risk profile, and reducing the complexity of an initial migration also reduces the risk associated with it. If this is an organization’s first foray into the cloud, starting small allows for quicker wins and demonstrable progress while helping teams learn and refine their processes before larger migrations take place.

Key benefits of tightly scoping the initial migration include:

• Manageable complexity: A smaller scope makes it easier to handle unforeseen challenges without overwhelming the team.
• Shorter learning curve: Team members can upskill and adapt to new cloud patterns more effectively with a focused, smaller-scale project.
• Reduced risk: It’s much easier to roll back or troubleshoot a small migration than a large one.
• Demonstrable success: Quick wins can build confidence among stakeholders and maintain momentum for future migration phases.

When scoping your initial migration, consider the following factors:

• Choose non-critical workloads: Start with applications or services that have minimal impact on core business operations.
• Select a representative sample: Choose a workload that represents common patterns in your infrastructure to maximize learning opportunities.
• Consider dependencies: Opt for applications with fewer dependencies to minimize complexity.
• Align with business goals: Ensure that the chosen workload aligns with your previously defined migration objectives.

Carefully scoping your initial migration sets the stage for a more successful overall cloud transition and builds a solid foundation for future, larger-scale migrations.

Identify IT assets to migrate

Once an initial set of workloads has been defined, it’s time to create a comprehensive inventory of applications, data, and infrastructure along with the connectivity and dependencies patterns among them. This step is vital for prioritizing IT assets by business impact and complexity as well as more accurately predicting cloud costs.

To effectively identify IT assets for migration, consider the following approaches:

• Leverage specialized tools: Utilize infrastructure discovery software to automate the process of mapping dependencies and creating a comprehensive inventory of assets to migrate. There are several purpose-built software suites designed to automatically discover and map IT assets across on-premises and cloud environments, identify complex application dependencies, and generate detailed reports on hardware, software, and network configurations.
• Conduct thorough assessments: Perform in-depth analysis of your current IT landscape, including the following aspects:
  • Application inventory: List all applications, their versions, and their  business criticality.
  • Infrastructure inventory: Document servers, storage, networking equipment, and their specifications.
  • Data inventory: Catalog databases, file shares, and other data repositories.
• Map dependencies: Understand the relationships among various IT components to ensure a smooth migration:
  • Application dependencies: Identify how applications interact with each other and with the underlying infrastructure.
  • Network dependencies: Document network configurations, firewall rules, and connectivity requirements.
  • Data dependencies: Determine how data flows between different systems and applications.
• Assess security and compliance: This stage is also an opportunity to uncover and address potential security and compliance considerations:
  • Identify sensitive data and its current protection measures.
  • Review existing security controls and how they might need to be adapted for the cloud; a great starting point is CSA resources.
  • Ensure that compliance requirements are understood and can be met in the target cloud environment.

Simple example of a blogging website’s dependency map

Creating a comprehensive inventory of your IT assets and their dependencies enables prioritizing workloads for migration based on complexity and business impact while predicting costs more accurately. It will also help you identify potential challenges or roadblocks earlier in the migration process and ensure that all necessary components are accounted for in the migration plan.

Using asset discovery tools can significantly streamline this process, providing detailed insights into your IT landscape and helping to ensure that no critical components or dependencies are overlooked when running a cloud migration assessment.

Select the best providers for each workload

When planning a cloud migration, it’s important to recognize that not all workloads are created equally, and different cloud providers may offer unique advantages for specific use cases. Each workload may be best suited to a different cloud provider, especially if they contain specialized use cases such as Oracle databases or Microsoft SQL Server on Azure with Hybrid Benefit.

Consider the following factors when selecting cloud providers for your workloads:

• Specialized services: Some providers excel in specific areas. For example, Microsoft Azure may be preferable for workloads heavily dependent on Microsoft technologies.
• Performance requirements: Evaluate the provider’s ability to meet your workload’s performance needs in terms of compute power, storage speed, and network latency.
• Geographical presence: Consider the provider’s data center locations to ensure compliance with data residency requirements and minimize latency for end-users.
• Cost structure: Compare pricing models across providers, taking into account factors like BYO licensing, reserved instances, spot pricing, and pay-as-you-go options.
• Integration capabilities: Assess how well the provider’s services integrate with your existing tools and processes.
• Support and SLAs: Review the level of support offered and the service level agreements (SLAs) provided by each cloud provider.

Carefully matching workloads to the most suitable cloud providers lets you optimize performance, cost-efficiency, and overall migration success, but bear in mind that each additional cloud provider introduces another layer of complexity. Choosing a single cloud provider that meets 80% of your requirements may be easier than adopting multiple cloud providers in an attempt to cover all use cases.

Define landing zone requirements

A well-designed landing zone provides a secure, compliant, and scalable environment for your migrated workloads. When defining landing zone requirements, consider the following aspects:

• Security and compliance:

• • • Review the security defaults and recommendations provided by the cloud service providers (CSPs) you’re evaluating.
    • Implement appropriate access controls, encryption, and network security measures.
    • Ensure compliance with relevant industry standards and regulations.

• Connectivity:

• • • Establish robust connectivity between on-premises and cloud environments.
    • Implement hybrid identity and networking patterns to ensure seamless integration.
    • Consider using virtual private networks (VPNs) or dedicated connections for secure, high-performance connectivity.

• Scalability and flexibility:

• • • Design the landing zone to accommodate future growth and changing requirements.
    • Implement infrastructure-as-code (IaC) practices for easy replication and modification of environments.

• Monitoring and governance:

• • • Connect monitoring and governance tools to existing solutions for a “single pane of glass” cloud management experience.
    • Implement logging and auditing mechanisms to maintain visibility across your hybrid environment.

• Cost management:

• • Set up cost allocation tags and budgeting tools to track and control cloud spending.
  • Implement policies for resource provisioning to prevent unexpected costs.

By thoroughly defining your landing zone requirements, you create a solid foundation for your migrated workloads and set the stage for future scalability and flexibility. Some organizations opt to develop a separate platform or DevOps team to manage cloud landing zones, but every IT administrator should work to become proficient in cloud technologies instead of passing the buck.

Migrate test and development workloads first

Starting the cloud migration with test and development workloads is not only less stressful but is a strategic approach that offers several additional benefits:

• Risk reduction: By not affecting production environments initially, you minimize the potential impact on critical business operations.
• Early issue identification: This approach provides opportunities to identify and address potential issues before they can affect more critical systems.
• Process refinement: You can refine migration procedures and best practices before tackling mission-critical workloads that have a higher negative business impact in case of failure.
• Confidence building: Successfully migrating test and development workloads builds confidence among the original stakeholders and the migration team.
• Skills development: This approach allows your team to gain hands-on experience with cloud technologies in a lower-stakes environment.

When migrating test and development workloads:

• Choose representative workloads that mirror the complexities and dependencies of your production environment.
• Use the migration as an opportunity to implement best practices for cloud-native development and testing.
• Document lessons learned and refine your migration playbook based on the experience—leverage an existing post mortem or retrospective process if your organization has one.

Wait to decommission the original hardware

While it may be tempting to claim success and immediately decommission on-premises hardware after migrating to the cloud, there are several reasons to maintain your original infrastructure for a period of time if the business allows it.

Keeping the original hardware ensures business continuity immediately following a cloud migration. This approach provides a safety net in case of unforeseen issues or missed configurations in the new cloud environment.

Maintaining the original infrastructure provides a reliable fallback option. If critical problems arise in the cloud environment, you can quickly revert to the on-premises setup, minimizing downtime and potential business impact.

Additional time with both environments running allows for more comprehensive testing and validation of migrated workload functionality. This ensures that all aspects of the migrated systems are working as expected in the cloud.

Keeping the original hardware operational for one to three months helps identify any overlooked dependencies on on-premises infrastructure. While using asset discovery tooling significantly reduces the likelihood of missing dependencies, some complex or legacy systems may have hidden interconnections that only become apparent during extended parallel operations.

When maintaining original hardware post-migration, you should still establish a clear timeline for the parallel operation period and implement proper access controls to ensure data consistency between environments. Both environments should be monitored closely to identify any discrepancies or issues, and a plan should then be established for a staged decommissioning process.

Conclusion

A successful cloud migration is the result of careful planning and incremental progress. Organizations should focus on defining clear business goals at the outset, scoping a realistic initial migration, and conducting a comprehensive inventory of IT assets and dependencies using best-in-class tools such as Device42.

Device 42 Basic Architecture (Source)

Device42 offers automatic discovery to provide visibility into complex IT environments to obtain a full inventory of assets to migrate, capturing detailed information about hardware, software, and dependencies prior to a migration.

Discovery Quality Scores from Device42 (Source)

While a cloud migration assessment is an excellent starting point, remember that cloud migration is not a one-time event but an ongoing process of optimization and refinement. Regularly reassess your cloud strategy, monitor performance and costs, and be prepared to adapt as your business needs evolve and cloud technologies advance.