Insight

Cloud Migration Strategy: Lessons from Enterprise Rollouts

By Hibba Limited · January 2026 · 7 min read

Migrating enterprise workloads to the cloud is one of the most impactful — and complex — IT programmes an organisation can undertake. Drawing from our experience with clients in energy, healthcare, and financial services, here are the key lessons that determine success or failure.

Lesson 1: Assess Before You Move

Too many organisations jump straight into migration without a thorough assessment. You need to understand your current estate — what applications you have, their dependencies, data volumes, compliance requirements, and which workloads are suitable for the cloud.

We use a 6R framework: Rehost, Replatform, Refactor, Repurchase, Retire, Retain. Not everything should move to the cloud, and the right strategy differs for each workload.

Lesson 2: Start Small, Scale Fast

Begin with non-critical workloads to build confidence and skills within the team. Once the process is proven, scale to business-critical applications. Trying to migrate everything at once is a recipe for failure.

Lesson 3: Security from Day One

Cloud security is a shared responsibility. Your provider secures the infrastructure; you secure your data, identities, and configurations. Implement identity management, encryption, network segmentation, and continuous monitoring from the very start.

Lesson 4: Cost Management is Ongoing

Lesson 5: Invest in Your People

The biggest barrier to cloud adoption is not technology — it's skills. Invest in training your teams on cloud platforms, DevOps practices, and Infrastructure as Code. The technology is only as effective as the people managing it.

"A successful cloud migration is 30% technology and 70% strategy, people, and process."

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