Technology and Licensing Videos

In this inaugural episode of the TSG podcast, Directions’ Barry Briggs, along with industry analysts George Gilbert and Peter O’Kelly, discuss Microsoft’s strategies in AI and beyond for 2026.

Microsoft’s one-pointed AI focus may be clouding what your company really wants and needs. Directions analyst Jim Gaynor shares with Mary Jo Foley some ideas for fighting back.

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!

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!

With AI, Microsoft is making the biggest bet in its history — a move many are comparing to the Industrial Revolution. 2026 is shaping up to be a critical year for Microsoft AI, the tech industry, and everyone who depends on Microsoft products. From Copilot to enterprise AI adoption, these decisions will define competitive advantage…

Microsoft is bundling more separately priced features with Microsoft 365 SKUs, making the imminent inevitability of an E7 less likely. Directions analyst Wes Miller talks through the details and customer impact with Mary Jo Foley.

Directions on Microsoft’s chief negotiator Dean Bedwell shares licensing and negotiation trends (along with a few tips) with Mary Jo Foley in our year-end wrap.

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!

As Microsoft transitions more customers off Enterprise Agreements and onto MCAs, orgs need to be aware of some potentially costly changes they may incur. Directions’ lead negotiator Dean Bedwell shares with Mary Jo Foley the biggest gotchas.

The Directions on Microsoft analysts assess recent changes and key trends in Microsoft’s enterprise technology roadmap. We look back at the most impactful announcements of 2025 and make predictions about what will matter in 2026.

As similar AI strategies and non-exclusive partnerships proliferate, are there still reasons to choose Azure over AWS (or vice versa)? Duckbill’s Corey Quinn joins Directions’ Wes Miller and Mary Jo Foley to debate the topic.

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!