In this episode of Late Night Brew, Robert Buktenica is joined by Josh Pusateri to unpack the role of discovery and planning in a Google Workspace to Microsoft 365 migration.
They explore why a clear understanding of your existing environment is essential before any data is moved, and how hidden complexity across users, labels, shared drives and permissions can quickly impact migration outcomes.
The discussion also highlights key challenges, including how Google specific structures such as labels and shared calendars translate into Microsoft 365, and why careful mapping and early decision making are critical to avoid issues later in the project.
In this episode, you will learn
• Why discovery is the foundation of a successful migration
• How to identify key data points in Google Workspace before migrating
• Why Gmail labels require careful handling in Microsoft 365
• How to approach mapping users and shared drives
• The importance of defining what data should and should not be migrated
• How large mailboxes impact migration timelines
Timestamps
00:00 Introduction and episode overview
01:35 Tools used for Google Workspace discovery
02:45 Key data extracted including users, labels and drives
03:45 Challenges with Gmail labels in Microsoft 365
05:05 Mapping users and shared drives
06:40 Data clean up and defining migration scope
07:20 Managing large mailboxes and migration timelines
08:59 Episode wrap up
If you are considering a move from Google Workspace to Microsoft 365, having the right plan in place is critical to success.
Our detailed eBook provides a deeper guide to the planning process, key risks and best practices to help you navigate the transition with confidence. Read the full guide Navigating the Transition Migrating from Google Workspace to Microsoft 365.
If you would like to discuss your migration strategy or better understand your environment before getting started, contact our team for expert guidance.





