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: 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…

Updated: May 21, 2026 Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs. Season 5. Episode 9.

Are you being hit with Azure consumption constraints and/or skyrocketing M365 costs in your Azure bill? Directions’ Advisory Services Director Lane Shelton shares with Mary Jo Foley his tips and advice on how to handle these issues.

Updated: July 7, 2026 Directions Atlas. What’s New? June 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: June 11, 2026 Too Big To Flail. Three Smart Guys: Season 1. Episode 5

Unlock the Future of AI: How Microsoft, Google, and Apple Are Shaping the Next Intelligent Client Are you ready to discover how the world’s biggest tech companies are redefining enterprise software, AI, and the intelligent client? Dive into this expert roundtable as industry veterans break down the latest from Google I/O, Microsoft Build, and more—revealing…