In the very first episode of Mind the Microsoft Gap, hosts Chris Trelfall and Nick Thomas dive into the fast-moving, high-stakes world of Microsoft 365 migrations, acquisitions and divestitures or as they call it, “Mind the Madness.” Whether you’re absorbing a new company, selling off a business unit, or moving from on-prem to cloud, these transformations are anything but straightforward.
With years of hands-on experience and plenty of war stories, Chris and Nick explore the technical, strategic and human elements that make or break these large-scale IT projects. From business continuity to security, identity clashes to communication breakdowns, they break it all down and offer insight into what successful execution really takes.
What You’ll Learn:
- Why MAD (Migrations, Acquisitions & Divestitures) projects are so complex — and risky
- How to plan for domain cutovers, email continuity, and minimal user disruption
- The top security risks during a migration and how to stay protected
- How modern tools and automation are changing the game for IT teams
- Why communication, governance, and naming conventions are crucial
- The value of “runbooks” and “lessons learned” for consistent project success
With real-world examples, expert insight, and a dose of humour, this episode is a must-listen for IT pros, project managers, and digital workplace leaders managing Microsoft 365 environments.
Timestamps & Topics
| Time | Topic |
| 0:00 – 1:30 | Welcome to the podcast & episode overview |
| 1:30 – 4:00 | What are migrations, acquisitions, and divestitures (MAD)? |
| 4:00 – 8:00 | Why MAD projects are growing — and more complex than expected |
| 8:00 – 12:00 | Security, compliance, and communication during change |
| 12:00 – 17:00 | Cross-platform challenges and hidden technical risks |
| 17:00 – 21:00 | Naming conflicts, email alias issues, and planning pitfalls |
| 21:00 – 25:00 | Cutover execution, tooling, and reducing downtime |
| 25:00 – 29:00 | Lessons learned, runbooks, and project delivery best practices |
| 29:00 – End | About Insentra & what’s coming next on the podcast |
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