Webinars & Videos

Our Analysts and Licensing Experts break down critical topics into concise, high-impact videos and webinars, ensuring your team is always ahead of Microsoft roadmap shifts and licensing changes.

Updated: November 5, 2026 Directions Atlas. What’s New? October 2026

Site Updates – What’s New This Month? Catch up on everything new on our site! In this video, we highlight the latest updates including: Stay up to date and make the most of your membership!

Not Ready for M365 G7? It Still Hits Your G3 and G5 Renewal

Microsoft 365 G7 went on sale to Government Community Cloud (GCC) customers on October 1. G7 is G5 plus Microsoft 365 Copilot, Microsoft Entra Suite, and Agent 365, and it now sits at the top of the Microsoft 365 government lineup. The announcement covered what G7 includes. It did not cover what G7 does to…

November 4, 2026 10:00 am – 11:00 am PT Request Access
Updated: October 6, 2026 Directions Atlas. What’s New? September 2026

Site Updates – What’s New This Month? Catch up on everything new on our site! In this video, we highlight the latest updates including: Stay up to date and make the most of your membership!

Updated: September 28, 2026 AI Doom or Golden Age? Three Smart Guys: Season 1. Episode 6

Are we doomed, or on the cusp of an AI-powered golden age? Can Claude’s Constitution, Microsoft’s Humanist AI Code of Conduct, or government regulation actually rein in AI, and should they? Directions on Microsoft’s Barry Briggs is joined by industry analysts Peter O’Kelly and George Gilbert to debate AI doom versus AI breakthrough, and whether…

Updated: September 17, 2026 Uncovering the Hidden Costs of M365 Copilot. Season 5. Episode 15.

Cowork consumption costs are just the tip of the iceberg when it comes to rapidly expanding M365 Copilot costs. Directions analyst David Berry lays out the potential gotchas in this episode with Mary Jo Foley.

Updated: September 10, 2026 How and Why We Built an AI Assistant. Season 5. Episode 14.

Directions on Microsoft built its own AI Assistant to help with Microsoft technology and licensing queries. Analysts Barry Briggs and Andrew Snodgrass share experiences and lessons learned with Mary Jo Foley.

Updated: August 6, 2026 Directions Atlas. What’s New? August 2026

Site Updates – What’s New This Month? Catch up on everything new on our site! In this video, we highlight the latest updates including: Stay up to date and make the most of your membership!

Updated: September 1, 2026 How the Changing Cyber Landscape Affects Your Org. Season 5. Episode 13.

The cybersecurity landscape is changing rapidly thanks to AI and other shifting dynamics. Directions on Microsoft Advisor Kathryn Mihalich shares her tips with Mary Jo Foley on what executives need to know to make the best technology and licensing decisions.

Updated: August 6, 2026 Directions Atlas. What’s New? July 2026

Site Updates – What’s New This Week? Catch up on everything new on our site! In this video, we highlight the latest updates including: Stay up to date and make the most of your membership!

Updated: July 9, 2026 Microsoft’s Fiscal 2027: What Enterprises Need to Know. Season 5. Episode 12.

Microsoft has established some high enterprise pricing and licensing hurdles going into its FY27. Directions’ Advisory Services Director Lane Shelton talks with Mary Jo Foley about the obstacles and potential opportunities.

Updated: June 25, 2026 What You Need to Know Before You Sign a Microsoft MEO. Season 5. Episode 11.

The Multiple Equivalent Offer is not the deal it may seem. Directions’ analyst Steve Kelley shares tips with Mary Jo Foley to help orgs make a MEO work more to their advantage.

Updated: June 11, 2026 Microsoft’s Evolving AI Strategy: New Clues from Build. Season 5. Episode 10.

Directions analyst David Berry sifts through the AI strategy announcements from Microsoft Build and discusses with Mary Jo Foley the potential impact on enterprises customers. Last week Microsoft held Build, one of its two biggest annual conferences. There were all kinds of announcements, from an Android-based device platform for agents, to seven new or updated…