Cloud Migration: Questions Every Business Owner Should Ask

Moving to the cloud is not automatic progress. Here are the questions that help determine if, when, and how your business should migrate.

Published 2026-01-31 by TechNet New England

Over 60% of businesses are planning to increase cloud spending in 2025. However, cloud migration is not universally beneficial - success depends on understanding your specific situation and requirements.

What Are You Actually Moving?

Cloud migration means different things to different organizations:

Software as a Service (SaaS)

Using cloud-based applications like Microsoft 365, Google Workspace, or industry-specific software. This is the simplest form of cloud adoption and is already common in most businesses.

Infrastructure as a Service (IaaS)

Running servers, storage, and networks in cloud platforms like AWS, Azure, or Google Cloud. This replaces physical servers but requires similar management expertise.

Platform as a Service (PaaS)

Using cloud platforms for application development and deployment. Primarily relevant for businesses that develop custom software.

Questions to Ask Before Migration

Why Are We Considering This?

Clarify your actual business objectives. Common drivers include:

Migration for its own sake, without clear business objectives, often leads to disappointment.

What Are the True Costs?

Cloud pricing models differ from traditional IT. Factors to consider:

Total cost of ownership comparisons should span 3-5 years including all these factors.

What About Our Existing Applications?

Not all software works in cloud environments. Legacy applications, specialized industry software, or systems with specific hardware requirements may need to remain on-premises or require significant modification.

How Will Security Change?

Cloud security is shared responsibility. Cloud providers secure infrastructure, but you remain responsible for:

What About Internet Dependency?

Cloud systems require reliable internet connectivity. If your internet goes down, can your business operate? Consider:

How Will We Handle Data?

Migration Approaches

Phased Migration

Moving systems incrementally reduces risk but extends the transition period and may require hybrid infrastructure.

Full Migration

Moving everything at once is faster but higher risk. Appropriate for smaller environments or when old systems cannot remain operational.

Hybrid Approach

Some workloads remain on-premises while others move to cloud. Common for organizations with specialized on-premises requirements.

When Cloud May Not Be the Answer

TechNet New England provides cloud readiness assessments and migration planning to help businesses make informed decisions.

Sources: Gartner Cloud Spending Projections, ISG Enterprise IT Budget Research, Industry Cloud Migration Best Practices