Migrating to Microsoft 365 isn’t just a technical move, it’s a full-scale transformation. Whether you’re transitioning from Google Workspace or legacy file shares, organizations often face a mix of logistical roadblocks and user resistance that can derail even the best-laid plans. To ensure a smooth journey, it’s essential to develop a well-rounded migration strategy that focuses as much on people as it does on technology.

In this blog, we’ll explore the three key stages of a successful migration; pre-migration, migration execution, and post-migration. Using a fictional company, BrewBean HQ, as our guide, we’ll highlight real-world challenges and actionable strategies IT teams can use to support users and meet business goals.

Pre-Migration: Planning for Success

The foundation of any successful migration lies in the prep work. For BrewBean HQ, a 500-person company with departments like Operations, Marketing, Finance, and HR, the goal was to move from Google Drive and file shares into Microsoft 365. Their objectives were clear: centralize content, improve collaboration, enhance security, and reduce downtime.

Build Your Migration Team and Define the Project Scope

Include IT professionals, project managers, and department champions. Identify business unit stakeholders early—this ensures ownership and accountability. Use a stakeholder matrix to track responsibilities and communication needs.

 Choose the Right Tools and Timelines

While Microsoft offers free tools like the SharePoint Migration Tool, third-party solutions like ShareGate are often preferred for their robust capabilities—delta migrations, metadata mapping, permission reviews, and governance support. Plan for both initial and final migrations, with timelines that account for Microsoft throttling and internal bandwidth constraints.

 Inventory, Cleanup, and Prep

Audit your content repositories. Use ROT (Redundant, Outdated, Trivial) analysis and create “Archive” and “To Be Deleted” folders. Assign department champions to lead cleanup efforts. Also, identify and document permission structures, start with a default model and note exceptions (e.g., HR confidential areas).

 Design Your New Architecture

Plan your SharePoint and OneDrive structure. Flatten folder hierarchies, define logical site collections, and use metadata tagging. Map source to destination paths clearly to reduce confusion post-migration.

Communication and Change Management

Develop a communications schedule:

• 4 weeks out: Announce the migration and its benefits.
• 3 weeks out: Share training resources.
• 2 weeks out: Provide tips and what to expect.
• 1 week out: Share go-live plans and support channels.
• Launch week: Reinforce support and provide quick links.

Use Teams, Viva Engage, and department champions to keep users informed and engaged.

Migration Execution: Managing the Move

With the groundwork laid, it’s time to execute. This stage requires high coordination, careful monitoring, and continuous communication.

Pilot Your Migration

Start with a department like HR. Validate tools, identify issues, and gather feedback. Use ShareGate to create migration plans and test configurations.

Migrate in Phases

Use a phased approach or an “all-at-once” strategy depending on your organization’s needs. BrewBean opted for phased rollouts to minimize disruption. Use bulk copy followed by delta sync to ensure all changes are captured.

Monitor Everything

Use ShareGate’s dashboards to track progress. Review logs for warnings and errors. Keep source systems in read-only mode during final migration to prevent data loss.

Post-Migration: Supporting Your Users

The migration may be complete, but success depends on user support, adoption, and continuous improvement.

Validate and Clean Up

Use ShareGate logs to verify success. Involve content owners in reviewing migrated data. Provide a “where is my data” map and decommission legacy systems only after thorough validation and backup.

Support Onboarding and Education

Offer a mix of training formats: cheat sheets, video tutorials, live sessions, and “Coffee Break Q&A” events. Tailor content to user roles and needs.

Drive Adoption and Build Community

Use internal campaigns, AMAs, and success stories to build momentum. Create a dedicated Teams channel or SharePoint site for ongoing support and tips.

Iterate and Improve

Monitor usage with Microsoft 365 reports. Conduct periodic permission reviews and content audits. Establish a governance committee or center of excellence to maintain standards and drive innovation.

Bonus: Training & Resources

To simplify user training, ShareGate offers over 15 hours of Microsoft 365 end-user content through its LMS-powered platform. With built-in quizzes, progress tracking, and modules for all skill levels, it’s an easy way to upskill your organization without extra lift. For partners, the ShareGate Partner Portal is a one-stop hub for deal tracking, training modules, and client resources to support smooth migrations and long-term success.

Final Thoughts

Migration is never without its challenges—but with the right strategy, tools, and a people-first approach, it can be a powerful catalyst for growth. Start early, plan thoroughly, and keep your users at the heart of the journey.