How to Get Ready For Your Cloud Migration

In previous articles, we’ve talked about the advantages of migrating to the cloud. Among the perks we discussed include instantly scalable computer power and storage, improved remote team support, enhanced collaboration and communication, and better budgeting.

For this article, we’ll help you uncover whether your organization is truly prepared to make the move.

We’ll share some insights we’ve gathered over the years, along with some actionable advice to assess whether your team has the right mix of strategy and expertise to avoid common pitfalls and navigate a smooth cloud transition.

Let’s dive in.

Step 1. Assessing Technical Readiness: Is Your Infrastructure Ready?

Assessing your technical readiness is the starting point to determine if your current IT setup is primed for a seamless cloud migration. This first step serves to develop an understanding of your complete technology stack i.e. the various applications, devices, and dependencies that undergird your network and business operations.

A thorough assessment safeguards your team from leaping into the unknown, providing an opportunity to identify challenges and potential bottlenecks before any actions take place. Overall, assessing technical readiness should help you avoid surprises and encounter less stress and more success during the transition phase.

Key areas of technical evaluation include:

1. Determining if existing hardware, servers, workstations, and network devices can support cloud integration or whether upgrades are needed.
2. All mission-critical applications and software dependencies must be analyzed to assess if they can function as expected in a cloud environment.
3. Network capabilities including internet speed, bandwidth, and reliability must be reviewed, as a stable and scalable connection is essential.
4. Security measures such as firewalls, VPNs, and access controls need to be examined to confirm sensitive business data remains protected during and after the transition.

Step 2. Assessing Operational Readiness: Are Your Processes and Workflows Cloud Friendly?

While a technical readiness assessment confirms that your tech stack can support the cloud, an operational readiness assessment checks how well your current business processes and workflows pair with cloud best practices.

For small and midsized businesses, this means ensuring outdated IT policies and habits won’t block the organization from fully reaping the rewards of the cloud.

The Key Focus Areas of an Operational Readiness Assessment

Step 3. Assessing Financial Readiness: What is the Business Case?

A financial readiness assessment examines your IT costs, budget, and long-term financial objectives to gauge the overall budgetary impact of cloud adoption.

Beyond direct costs, SMBs should assess potential savings and efficiency gains, such as reduced hardware expenditures, lower energy consumption, and scalability benefits that allow businesses to pay only for the resources they use. It’s also important to factor in hidden costs like migration expenses, training for employees, and possible downtime during the transition.

Ultimately, a financial readiness assessment should clarify your potential return on investment (ROI), as well as help leaders understand the full economic value cloud adoption will deliver.

Step 4. Organizational Readiness: How Will Your Staff Transition?

Moving to the cloud isn’t just about upgrading technology – it’s a fundamental transformation in how your SMB operates. Yet, many businesses focus solely on costs and infrastructure while neglecting the human element.

A common mistake is viewing the cloud as nothing more than a fancy remote data center. Unlocking its full potential requires a company-wide mindset shift, where teams willingly embrace new workflows, automation, and digital collaboration.

Furthermore, without investing in upskilling and retraining, even the best cloud strategy will fall short. Successful adoption demands buy-in across all departments at all levels, with IT leaders at the forefront.

Cloud Readiness Checklist and Questions

As we’ve highlighted, migrating to the cloud is an immense undertaking that requires careful planning and persistent diligence. This section provides a concise checklist, and critical questions guide to support your team as you progress along your journey.

Technical Readiness Checklist and Questions

• Evaluate whether “lift and shift”, “refactoring”, “re-platforming”, or “repurchasing” is the right migration strategy for your business.
• Some applications require separate cloud licenses or subscription-based pricing – factor this into your budget.
• Can your data be easily transferred, or does it need reformatting or restructuring before safely moving to the cloud?
• If your industry has regulations (HIPAA, GDPR, SOX, CCPA, etc.), verify that cloud providers meet all necessary standards.

Operational Readiness Checklist and Questions

• Identify processes that need to be removed, optimized, or automated for better efficiency.
• Develop a detailed migration roadmap with phased implementation, clear milestones, and contingency plans.
• Establish clear guidelines for data ownership, access control, and policy enforcement.
• Evaluate current backup strategies and ensure redundancy, failover mechanisms, and recovery protocols are in place to minimize downtime and data loss
• What are the potential performance implications for your most mission-critical applications?

Financial Readiness Checklist and Questions

• Do you know which cloud approach best aligns with your overall financial and business goals?
• Are you locking yourself into a single provider with escalating fees? Remember, when it comes to vendor lock-in, what is cheap now, can be expensive later.
• How much data are you moving, and how expensive will it be to transfer terabytes (or petabytes) to the cloud?
• Some apps won’t move cleanly. Are you budgeting for rewriting and or replacing old software?
• How much revenue (per hour, per day, etc.) will you lose if your transition isn’t seamless? Do you have a backup plan?
• What KPIs define success for your cloud move? Cost per transaction? Uptime? Productivity gains? Define them before you migrate.

Organizational Readiness Checklist and Questions

• Is there clear executive buy-in? Leadership must champion the cloud not as an IT upgrade but as a business transformation.
• Do teams understand that the cloud enables automation, scalability, and new workflows – not just storage and computing?
• Have you articulated how cloud adoption improves agility, efficiency, and collaboration across departments?
• What cloud-based tools and workflows do sales, finance, and customer support teams need to master?
• Is there a resource center to help employees with FAQs, training guides, and troubleshooting issues?
• Is cloud adoption seen as an evolving strategy rather than a one-time project?

Partner with a Cloud Expert on Your Migration

That should give you a solid understanding of your organization’s cloud readiness, from infrastructure and cost estimates to security and the people who will drive success. What comes next?

If you’re ready to take the leap but unsure of the best path forward, a qualified cloud migration partner can help you make more strategic decisions required for a smooth transition.

The Complete Network team is here to help! For over 20 years, we’ve been helping businesses make a safe and secure journey to the cloud. Contact us any time at (844) 426-7844. We look forward to speaking with you.