The 5 Questions That Prevent Email Migration Disasters

Moving your business email from one system to another sounds straightforward until it isn't. Susan learned this the hard way during a weekend-long migration that revealed every hidden complexity you never think to ask about upfront. In this episode, she breaks down the five critical questions every business owner must answer before switching email systems - questions that could save you from your own technical nightmare and budget explosion.

The 5 Questions That Prevent Email Migration Disasters

1. How big are your mailboxes, and where is your old mail stored? Large mailboxes with years of Sent/Deleted items cause export failures. You need to know mailbox sizes and whether users keep local PST files before you can estimate the timeline.
2. Who will be available during the actual migration for testing and approvals? Migrations require live client participation for password resets, login approvals, and testing. Without committed availability, projects stall.
3. How do your users actually access their email today? Classic Outlook, new Outlook, web-only, mobile apps - each requires different configuration steps. Mixed environments multiply complexity.
4. What domains and aliases are tied to your current email system? Hidden alias domains and Microsoft's "ownership" of domains can prevent a clean cutover to Google. You need the complete domain picture upfront.
5. Do you need to keep Microsoft Office apps or other integrations? Many businesses use Microsoft 365 for more than email. Licensing decisions affect migration approach and ongoing costs.

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Blog series on the topic of tech stacks and email migration.