Is Your Business Ready for Cloud Migration?

Common triggers: hardware end-of-life, an acquisition or major growth event, regulatory or contractual cloud requirements, modernization of legacy applications, or a clear cost or agility business case. Migrating without a specific business driver frequently produces expensive moves that did not need to happen; tying the migration to a specific business outcome is the foundation.

Gartner cloud-migration research places typical mid-market migrations at 6-18 months end-to-end, depending on application count, complexity, data volume, and team capacity. Migrations compressed into shorter timelines without prerequisite readiness routinely overrun on cost and produce operational pain post-migration that takes years to unwind.

Rehosting (lift-and-shift) moves the application as-is to cloud infrastructure with minimal change. Refactoring rebuilds parts of the application for cloud-native operation (databases, scaling, services). Retiring removes the application entirely when a SaaS replacement or business-process change eliminates the need. Most migration plans use a mix; the right mix depends on application priority and cloud-readiness per app.

Cloud is not automatically cheaper than on-premise; without disciplined FinOps practice (cost monitoring, right-sizing, reserved capacity, auto-shutdown of non-production), cloud spend frequently exceeds equivalent on-premise costs. Mature cloud operations with FinOps discipline typically deliver agility and scale benefits at comparable or modestly lower TCO over a 3-5 year window.

Yes, sharing with your IT lead, CFO, or managed service provider typically multiplies the value. The assessment scores five readiness dimensions (current infrastructure, application compatibility, data and security, team skills, and budget and business drivers), and the lowest-scoring dimension is almost always the one that surprises someone on the team. Flexera State of the Cloud research identifies team-skill gaps and FinOps capability as the two readiness dimensions most frequently underestimated by the person who initiated the migration; a second reviewer with direct visibility into those areas often catches the gap that the initiator missed.

The most common categories: fully managed IT (MSP) covering helpdesk plus operations, managed helpdesk and user support, managed cybersecurity services (MSSP), cloud services and migration, backup and disaster recovery, compliance readiness and vCISO, virtual CIO and IT strategy, network and connectivity services, and project-based IT consulting.

Common signals: a solo or junior IT person handling more than they can manage, recurring fires across security and operations, mission-critical uptime requirements that exceed in-house coverage capacity, growth that is outpacing IT hiring, or a budget where MSP retainers fit at or below the loaded cost of equivalent in-house staffing.

Backup is the practice of creating copies of data; disaster recovery (DR) is the broader practice of restoring business operations after an event, including backup restoration plus infrastructure rebuild, application failover, and process resumption.

MIT Sloan and Boston Consulting Group AI research consistently identifies five readiness foundations: clean and accessible business data, one or two specific use cases tied to measurable business outcomes, AI skills internally or through a trusted partner, documented AI governance covering data privacy and acceptable use, and leadership sponsorship with defined budget.

Mid-market businesses without existing security controls typically need 6-12 months from project start to SOC 2 Type 1 readiness, and an additional 3-12 months of operational observation period for SOC 2 Type 2.