9 Questions for a Microsoft 365 Migration Checklist (Copilot Ready)

Migrating to Microsoft 365 (formerly Office 365) isn’t just a software upgrade—it’s a digital transformation.

Today’s migration isn’t only about moving emails; it’s about enabling hybrid work, preparing your data for Microsoft Copilot, and implementing modern security strategies like Zero Trust.

This checklist covers the questions you need to ask before switching, so your migration is smooth, secure, and future-ready.

9 Key Questions for a Successful Microsoft 365 Migration

1. Is your data “AI-ready” for Microsoft Copilot?

With AI becoming a core part of Microsoft 365, ensuring your data is clean, well-labeled, and properly governed is critical. Copilot works best when sensitive information is protected, and data is organized consistently across Exchange Online, SharePoint, and OneDrive. Over-sharing or mismanaged files can lead to compliance and productivity issues.

2. Have you implemented Zero Trust security measures?

Modern migrations demand modern security. Implement Multi-Factor Authentication (MFA), Conditional Access policies, and endpoint compliance using Entra ID (formerly Azure AD) and Intune.

Zero Trust isn’t optional; it’s a requirement to protect sensitive data and prevent breaches during and after migration.

3. How will you map on-prem file shares to SharePoint & Teams?

Moving files to the cloud isn’t just copying data. You need a plan for SharePoint and Teams structures, permissions, and OneDrive synchronization.

Clear mapping prevents confusion, ensures security, and sets the stage for collaboration in a hybrid environment.

4. Do you have a Change Management & Training plan?

User adoption is often the biggest hurdle in migrations. Plan for Champions Programs, training sessions, and internal communication campaigns.

Teams, SharePoint, and OneDrive all have new workflows, and supporting users early ensures a smoother transition.

5. What’s your Exchange Online migration strategy?

Decide whether a cutover, staged, or hybrid migration best fits your organization. Consider email coexistence, calendar continuity, and archive strategies. Enterprise migrations may take months, so plan accordingly.

6. How will you manage devices and endpoints?

Leverage Intune for device compliance, Windows 11 readiness, and BYOD policies. Device management ensures secure access to M365 apps and protects company data across all endpoints.

7. Are compliance and retention policies aligned?

Set up retention labels, legal hold policies, and records management in SharePoint and Exchange Online. Ensuring compliance before migration prevents future audit headaches and maintains organizational governance.

8. Have you tested Microsoft Teams integrations and apps?

Check line-of-business apps, Power Automate flows, and third-party integrations. Proper testing ensures collaboration and workflow continuity from day one.

9. What’s your migration timeline and post-migration support plan?

Plan realistically based on company size and complexity. Include post-migration support for troubleshooting, adoption, and ongoing governance.