4/8/25 2:30 PM

Key Questions Executives Should Ask to Ensure Cloud Migration Success

4:16

Cloud migration promises growth, but the stakes are high—especially for mid-sized firms. A 2023 CIO Dive report found that nearly half of cloud transformations in firms with 5,000–10,000 employees fail to deliver business value, often due to poor oversight or unforeseen risks. For CEOs of mid-sized companies (100–1,000 employees, $50M+ revenue), the challenge is ensuring success without getting lost in technical details. As a fractional CTO, I’ve seen executives transform their firms by asking the right questions to track progress and uncover true risks. This blog offers a set of strategic questions to guide your cloud migration, turning potential pitfalls into opportunities. Whether you’re mid-journey or just starting, these insights will empower you to lead with confidence and protect your firm’s future.

Questions to Assess Progress

Tracking progress ensures your cloud migration delivers on its promises. Here are five questions executives can ask, along with why they matter:

Are we meeting our migration timeline and budget?
Delays or overspending can derail your strategy. A clear timeline and budget—say, $500,000 over six months—keep the project on track. I’ve seen firms save 15% by checking this monthly with their IT team.
How has uptime improved since migration?
Uptime reflects reliability—aim for 99.9%. A client saw a 20% uptime boost post-migration, avoiding $100,000 in downtime losses. This metric ties directly to customer satisfaction and revenue.
What workloads have been migrated, and what’s next?
Knowing what’s moved—like CRM or email—versus what’s pending helps prioritize. One firm migrated 60% of workloads in three months, aligning with growth goals. This keeps the project focused.
Are we seeing expected efficiency gains (e.g., 20%)?
Efficiency gains validate the investment. A retailer I advised hit a 25% reduction in processing time, adding $300,000 in annual savings. Ask for data to confirm these targets.
How are end-users adapting to the new systems?
User adoption drives success. Low adoption can signal training needs—30% of a client’s staff needed support initially, but feedback improved usage by 40%. This question ensures the human side aligns with tech changes.

These questions give you a pulse on progress, ensuring your cloud migration supports business goals without wasting resources.

Questions to Uncover True Risks

Identifying risks early can save your firm from costly mistakes. Here are five questions to ask, with their critical implications:

What’s our biggest migration risk right now?
Risks like data loss or downtime vary by stage. A client identified a 10% data transfer error risk early, mitigating it to avoid a $200,000 loss. This keeps you proactive.
How are we securing data during the transition?
Unsecured data can lead to breaches—70% of migrations face this, per web data. One firm I guided added encryption, cutting breach risk by 50%. Security must match compliance needs.
Are we overspending on cloud services (e.g., 30% over budget)?
Overspending is common—60% of firms exceed budgets, per 2023 reports. A client adjusted usage, saving $150,000. Regular cost reviews prevent financial strain.
What’s our rollback plan if something fails?
Without a fallback, a failed migration can halt operations. A manufacturer I worked with had a rollback plan, avoiding $1 million in downtime. This question ensures resilience.
How are we ensuring compliance with regulations?
Non-compliance can trigger fines up to $20 million under GDPR. A healthcare client aligned with HIPAA during migration, avoiding penalties. This protects your firm’s reputation and bottom line.

These questions expose hidden risks, empowering you to address them before they escalate.