Cloud migration strategy: Best practices for IT admins

A cloud migration strategy is a plan that helps IT teams move content and workloads from on-premises environments—like SharePoint Server or file shares—to Microsoft 365. This includes services like SharePoint Online, OneDrive for Business, and Microsoft Teams, which work together to support collaboration, content management, and productivity in the cloud.

For many organizations, the move is driven by the need for better scalability, easier access to content, and tighter integration between tools. But for teams running SharePoint Server 2016 or 2019, there’s also a more immediate deadline to consider. On July 14, 2026, Microsoft ends support for both versions. After that point, organizations will no longer receive security updates or technical support, making it harder to stay secure and compliant over time.

That doesn’t mean every organization needs to move to Microsoft 365 right away. Some will choose hybrid setups or upgrade to SharePoint Subscription Edition. But for many IT teams, migrating to Microsoft 365 is the most practical long-term path forward.

That’s where having a clear migration strategy matters.

In this guide, we’ll break down why a structured approach is critical for on-prem to Microsoft 365 migrations, what IT teams need to evaluate before getting started, common challenges to plan for, and best practices to help you run a smooth, controlled migration.

Why a strong cloud migration strategy matters

A strong cloud migration strategy helps IT teams reduce risk, control disruption, plan costs, and move to Microsoft 365 with fewer surprises. Here’s what IT admins gain when the migration is planned, not rushed.

Risk mitigation

A migration plan helps IT teams spot issues before they turn into project blockers. For SharePoint and Microsoft 365 migrations, that means assessing your content, permissions, metadata, customizations, and site structure before you start moving data.

This gives admins a clearer view of what can move as-is, what needs cleanup, and what may need to be reworked for SharePoint Online.

Minimized disruptions

A phased migration helps keep work moving. Start with a pilot group, validate the migration plan, gather feedback, and then roll out in waves.

That way, if something needs adjusting, IT can fix it before it affects the entire organization.

Cost predictability

Migration planning helps IT teams understand the real cost of the move, including licensing, migration tools, storage, support, and the time needed to run legacy and cloud environments in parallel.

By mapping what needs to stay active, what can be retired, and which licenses are actually required, teams can avoid surprise costs during the transition.

Team alignment

Cloud migration touches more than IT. A clear plan helps define who owns what before the work begins.

Leadership sets direction and scope. IT admins handle migration planning, configuration, and execution. Business owners validate content, clean up data, and confirm what still needs to move.

When ownership is clear, decisions move faster and fewer issues get stuck in limbo.

Smoother Microsoft 365 service integration

A migration is a chance to rethink how SharePoint, Teams, OneDrive, and Microsoft 365 services work together.

Before moving content, IT teams can identify inactive sites, simplify outdated structures, review permissions, and reduce duplicate or obsolete content. That groundwork helps create a cleaner Microsoft 365 environment, not just a cloud copy of the old one.

Evaluate these factors before migrating

A successful migration starts with a clear understanding of your current environment, your Microsoft 365 goals, and the risks that could slow the project down. Here’s what IT teams should review before they move.

Governance, security, and compliance

Review your current on-premises policies to see what will translate to Microsoft 365. To do so, use tools like:

• Microsoft Purview for governance and compliance
• Microsoft Defender for enhanced threat protection
• Microsoft Entra ID for identity and access management

Map your on-premises controls by tying the policy intent (what it’s protecting or enforcing) to the related Microsoft 365 features. This includes retention policies, sensitivity labels, and data loss prevention (DLP) features.

User adoption and training

Even a technically successful migration can fall flat if users don’t know what changed. Give IT teams and end users clear guidance on where content lives, how permissions work, and what to do differently in Microsoft 365.

Use pilot feedback, surveys, and support tickets to spot knowledge gaps early and adjust training before the broader rollout.

Differences between on-premises vs. modern Microsoft 365 architecture

Modern SharePoint favors a flatter structure over deeply nested subsites. Instead of building large hierarchies, IT teams can create separate sites for distinct teams, projects, or business needs, then connect them with hubs and navigation.

This makes the environment easier to manage over time and gives IT a chance to review legacy customizations, outdated lists, and structures that may not fit well in modern SharePoint.

Adapting to the self-service governance model

Microsoft 365 gives users more flexibility to create, share, and collaborate. But that doesn’t mean IT steps away.

Instead, IT needs to set guardrails upfront: who can create workspaces, how external sharing works, when access should be reviewed, and what policies apply to sensitive content.

The goal is to give users enough freedom to work efficiently while keeping ownership, permissions, and compliance under control.

Managing costs

At this point, you’ll need to decide which tools to use. Most third-party software offers pricing models based on the amount of data, users, or workloads you use. ShareGate Migrate is an exception. Get unlimited data, users, and every available Microsoft 365 migration workload—all for a single flat fee.

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Key components of a pre-migration plan

A comprehensive pre-migration plan covers at least these elements:

• Pre-migration audit: Review your existing content, structure, permissions, and customizations to understand what you’re migrating. Not everything needs to be fixed upfront. The goal is to identify what could impact the migration and decide what to address before, during, or after the move.
• Phased hybrid approach: Move in stages instead of all at once. A phased rollout helps reduce business disruption, validate your approach early, and gives IT time to adjust before scaling to the full organization.
• Migration validation: Validate that your content was migrated as expected. That includes checking file counts, permissions, metadata, and structure so users can find and access what they need after the move.
• Post-migration optimization: After the migration, monitor usage, clean up unused content, and refine governance settings. This helps ensure your new Microsoft 365 environment stays organized, secure, and easy to manage over time.

7 steps for a seamless Microsoft 365 transition

Try these best practices for creating a migration strategy that steers clear of common migration headaches.

1. Define clear success criteria before getting started

Based on business goals like reducing downtime or controlling costs, pick which criteria to track. Choose specific metrics like cutover date, user adoption, or ease of use. Get input from leaders and IT admins, and document these success metrics in a shared project brief for easy visibility.

2. Conduct a full content and workload inventory

Use a pre-migration assessment tool to inventory your environment—file shares, SharePoint sites, permissions, and metadata. This helps you understand what needs to move, what can be archived, and what requires cleanup.

3. Design a phased, low-risk migration approach

Start your cloud migration methodology with a pilot group of employees to uncover any serious initial issues. Choose users who represent real business scenarios and can provide actionable feedback. Then expand in phases to reduce risk and improve rollout quality.

4. Factor in user adoption and change management

Plan for user adoption early. Focus training on what’s changing—where content lives, how to collaborate, and what workflows look like in Microsoft 365. Use feedback and support trends to adjust training as you roll out.

5. Bake in governance and security from day one

Define governance and security early by setting rules for access, sharing, and content classification. Document clear rules for access, ownership, and external sharing. Define who can create workspaces, who owns content, and how access is reviewed over time. This keeps your environment manageable as it grows.

Microsoft Purview supports compliance scenarios like retention, sensitivity labels, and DLP. But governance in Microsoft 365 spans multiple tools. The key is aligning policies across identity, security, and collaboration.

6. Incorporate post-migration validation and optimization

Use a validation checklist to confirm the migration was successful. Include steps for:

• Data verification: Confirm that files, lists, and items migrated completely.
• Permissions: Verify that access levels align with expectations.
• Metadata integrity: Check that key metadata fields and structures are preserved where needed.

7. Find the perfect migration tool for your environment/project

ShareGate helps simplify complex migrations by giving IT teams visibility and control throughout the process, from planning to validation. You’ll get:

• Pre-migration checks to flag issues before they become emergencies
• Assessment reporting for accurate planning, scoping, and estimation
• Predictable steps through phased migration without starting from scratch
• Easy migration of files, lists, and metadata
• Flexible migration options, including the ability to restructure content and modernize your SharePoint environment as you move
• Detailed insights on migration progress and outcomes through robust reporting
• Scale your migration with high-performance processing across multiple machines
• Move as much data as you need without worrying about per-user or per-gigabyte limits

Microsoft 365 migration, without the chaos

Migration doesn't have to mean months of disruption, runaway costs, and frantic PowerShell sessions at 11 pm. With ShareGate Migrate, you get everything you need to move to Microsoft 365 the right way. Clean, complete, and on schedule.

No data caps. No metadata surprises. No scripting required.

• Move as much as you need, no artificial limits
• Permissions and metadata migrate exactly where they should
• Built-in reporting, delta migrations, and scheduling so nothing slips through
• Drag-and-drop interface. Leave the scripts to someone else.

Microsoft 365 migration, we got this. Try ShareGate today.

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