Moving to Microsoft 365: What Canadian Businesses Should Know Before They Start

Microsoft 365 has become the default workplace platform for Canadian businesses of all sizes. Teams for communication, Exchange Online for email, SharePoint and OneDrive for file storage—the integrated suite eliminates several separate tools while improving security and compliance posture.

But migrations go wrong more often than vendors admit. Here's what to know before you start.

Plan the migration—don't wing it

The most common mistake is treating a Microsoft 365 migration as a weekend project. Even for a 25-person company, a proper migration involves:

• Tenant setup and security baseline — Conditional Access policies, MFA enforcement, audit logging
• Identity decisions — Are you syncing with on-premises Active Directory, or going cloud-only? This affects how users authenticate across every Microsoft service.
• Mailbox migration strategy — Cutover, staged, or hybrid migration; each has tradeoffs depending on your current email platform
• SharePoint and OneDrive architecture — Where does shared file storage live? Who owns what? What gets migrated vs. archived?
• Teams structure — How will you organize Teams and channels? Governance upfront prevents sprawl later.
• Licensing — Microsoft 365 Business Basic, Business Standard, Business Premium, and E3/E5 have meaningful feature differences. Mischoosing costs you either money or functionality.

A migration plan for a 50-person business should take two weeks to write and review—before a single mailbox is moved.

Licensing: what you actually need

Microsoft's licensing tiers confuse even experienced IT professionals. A rough guide for SMEs:

For most Canadian SMEs, Business Premium is the right answer. The added security features—particularly Intune for device management and Defender for Business—are worth the cost difference, especially if your team works on laptops outside the office.

Data migration: what to expect

Email migration is usually the smoothest part. MigrationWiz, ShareGate, or Microsoft's native IMAP migration tool handles most scenarios. Budget for user training on Outlook changes, particularly calendar and contact sync behaviour.

File migration is where projects stall. Common issues:

• SharePoint has path length and character restrictions that cause migration errors
• Legacy folder structures don't translate cleanly to SharePoint/OneDrive
• Users who stored files locally (rather than on a server) need separate handling

Before migrating files, clean up. Remove duplicates, archive old projects, and agree on a new folder structure. Don't migrate chaos into SharePoint and expect it to sort itself out.

Teams adoption is a change management problem, not a technical one. If your team has been using email for everything, Teams requires a shift in how people communicate. Invest time in training and set clear norms about what goes in Teams vs. email.

Security baseline: don't skip this

Microsoft 365's default settings are not secure defaults. Before you migrate, configure:

• Multi-factor authentication — Enforce for all users, no exceptions
• Conditional Access policies — Block sign-ins from unexpected countries; require compliant devices
• Audit log retention — Enable unified audit logging; retain for at least 90 days
• External sharing settings — Lock down SharePoint and OneDrive external sharing to your business needs
• Anti-phishing and anti-spam policies — Microsoft Defender for Office 365 (included in Business Premium) adds significant protection

Skipping these and cleaning up a compromised tenant later is far more expensive than doing it right at migration time.

Post-migration: the first 90 days

Expect a support spike in the two weeks after go-live. Users will have questions about Outlook, OneDrive sync, and Teams. Plan for it—don't assume everyone will figure it out.

At the 30-day mark, review:

• License utilization (unused licenses are money on the table)
• Teams and SharePoint usage (are people actually using the new tools?)
• Any security alerts from Defender

At 90 days, conduct a lightweight governance review. Have users created rogue Teams channels? Is external sharing enabled somewhere it shouldn't be?

MicroPro manages Microsoft 365 migrations and ongoing administration for businesses across Toronto and PEI. Our Microsoft 365 service covers planning, migration, security baseline, and post-go-live support. Get in touch if you're planning a migration and want to avoid the common pitfalls.