From Legacy to Leading Edge: Navigating Cloud Migration

Cloud migration has evolved from a nice-to-have initiative to a business-critical imperative. As organizations face increasing pressure to consolidate digital environments following mergers, acquisitions and divestitures, IT leaders must navigate complex technical and organizational challenges while maintaining business continuity.

The shift isn’t just about moving data – it’s about transforming how your organization operates. Legacy systems that once served as reliable workhorses now create bottlenecks that hinder agility, increase operational risk and limit collaboration across teams and geographies.

For IT leaders, the question isn’t whether to migrate, but how to execute a seamless transition that protects business operations while positioning the organization for future growth.

The current business environment has accelerated the need for digital consolidation. Mergers, acquisitions and divestitures are happening at an unprecedented pace, creating urgent demands to bring disparate digital environments together quickly and efficiently.

Legacy systems present significant challenges in this context. On premises infrastructure limits organizational agility and creates unnecessary complexity when integrating acquired companies. These systems often rely on outdated security protocols, making them vulnerable to modern threats while increasing compliance risks.

Perhaps most importantly, executives are prioritizing seamless transitions that protect business continuity and brand integrity. When one organization acquires another, business operations cannot pause for weeks while systems are migrated. The expectation is clear: employees should arrive Monday morning and find their news systems operational with minimal disruption to their workflow.

Cloud-to-cloud migrations represent the new frontier of complexity that goes far beyond traditional lift-and-shift exercises. These projects involve intricate considerations around identity management, security protocols, compliance requirements and user experience design.

Modern migrations must address overlapping systems where source and target environments may have conflicting security policies or authentication methods. For example, a manufacturing company with government contracts acquiring a smaller firm will need to elevate security standards across the entire organization — a change that affects every user and system.

Incompatible configurations create additional challenges. When moving between cloud environments, organizations often discover that their existing workflows, integrations and customizations don’t translate directly. This complexity, combined with tight timeless driven by business requirements, creates significant risk.

Success requires a structured approach built on four foundational phases:

1. Comprehensive discovery to understand both source and target environments.
2. Detailed design planning that accounts for all integration points.
3. Thorough testing to validate functionality before go-live.
4. Precise execution aligned to specific business outcomes.

Technology migrations fail when organizations focus solely on technical aspects while neglecting the human element. User adoption is the ultimate measure of migration success, and it requires deliberate attention from day one.

Executive sponsorship provides weight necessary to drive change. Without clear leadership support and communication about why the migration matters, employees often resist new systems or revert to familiar workarounds that undermine the project’s value.

Clear communication throughout the migration process helps employees understand not just what’s changing, but why changes are necessary and how they’ll benefit from new capabilities. This communication must be tailored to different audiences — executives need strategic context while end users need practical guidance about their daily workflows.

Training programs must address the specific needs of different user groups. A sales team migrating to a new customer relationship management (CRM) system has different concerns than IT administrators managing new security protocols. Effective change management recognizes these differences and provides targeted support.

Most importantly, change management cannot be treated as an afterthought or final phase activity. It must be embedded throughout the migration process, from initial planning through post-migration support.

Organizations that succeed treat migrations as transformation opportunities rather than simple IT projects. They use the migration as a catalyst to modernize processes, improve security posture and enhance collaboration capabilities.

Common snags consistently emerge across industries. Unrealistic stakeholder timelines create pressure that leads to shortcuts and increased risk. The expectation that an acquired company can be fully integrated in 30 days rarely accounts for the complexity involved in evaluating systems, planning integrations and supporting users through change.

Underestimating scope represents yet another frequent challenge. What appears to be a straightforward data migration often involves legacy systems, custom integrations and regulatory requirements that weren’t apparent during initial assessments. For example, a hospital migration might involve 8.6 terabytes of data across 5,000 mailboxes, 7,000 laptops and complex integrations with medical systems far more complex than initially anticipated.

Neglecting the user journey creates adoption challenges that persist long after technical migration is complete. Users who don’t understand how to access their data or perform routine tasks will struggle with productivity and may resist the new environment entirely.

Successful migration starts with a comprehensive data gathering and readiness assessment. Organizations need clear visibility into their current environment — not just what systems exist, but how they’re used, who has access and what dependencies exist between systems.

Stakeholder alignment ensures that business leaders, IT teams and end users share common expectations about timeline, scope and success criteria. This alignment prevents scope creep and reduces the risk of unrealistic demands during execution.

Engaging an experienced partner such as CDW provides access to proven methodologies, specialized tools and expertise across multiple platforms and industries. Organizations that attempt complex migrations without this support often encounter unexpected challenges that delay projects and increase costs.

Cloud migration represents more than a technical upgrade; it’s an opportunity to modernize how your organization operates and collaborates. By addressing the strategic, technical and human dimensions of migration, IT leaders can deliver transformative results that position your organization for sustained success.