The Directions on Microsoft Briefing Podcast
Directions on Microsoft
With more than 30 years of experience covering Microsoft, Directions on Microsoft provides unique perspectives about the shifts in Microsoft technologies, roadmaps and licensing policies that matter most to enterprise-size companies. Twice each month industry veteran Mary Jo Foley interviews a different Directions analyst for informed insights and advice to help you derive full value from your Microsoft investments.
Episodes
Mentioned books
Mar 26, 2026 • 34min
Three Smart Guys: Is Office Dead?
Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly discuss if and how AI could be making Microsoft's core Office apps more replaceable.
Mar 12, 2026 • 25min
What We Know (and Don't) About M365 E7
Beyond the known price tag and release date, there are still a lot of E7 unknowns. Directions' Advisory Services Director Lane Shelton shares his E7 educated guesses and customer advice with Mary Jo Foley.
Mar 4, 2026 • 33min
Three Smart Guys: It's All About the Data
Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly discuss how AI’s dependence on data is reshaping Microsoft’s enterprise strategy.
Feb 19, 2026 • 37min
Microsoft 365 Copilot Licensing: Five Things You Need to Know
Rob Horwitz, Microsoft licensing analyst and co-founder of Directions on Microsoft, explains Microsoft 365 Copilot licensing and deployment. He covers why licensing is changing and the free Copilot Chat versus paid tiers. He outlines a four-layer model from basic chat to advanced agents. He also highlights hidden costs, security tradeoffs, and negotiation strategies for buying Copilot.
Feb 12, 2026 • 25min
SQL Server Migrations: Tips to Help You Prepare
SQL Server 2016 and 2017 are leaving Extended support in the not-too-distant future. Directions' analyst Andrew Snodgrass shares his preparation checklist in this episode with Mary Jo Foley.
Jan 29, 2026 • 30min
Three Smart Guys: Microsoft's 2026 Challenges
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.
Jan 23, 2026 • 24min
Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
Jim Gaynor, who leads the Directions on Microsoft editorial team and analyzes Microsoft enterprise tech, talks about Microsoft’s intense AI push and how it crowds out other products. He names Windows Server, Intune and management tools as areas feeling neglected. He outlines negotiation tactics, when to wait on AI, and how competition from Apple and Google can help.
Jan 8, 2026 • 17min
What Microsoft's Recent M365 Bundling Moves Mean for You
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.
Dec 22, 2025 • 20min
Microsoft Licensing and Negotiation: A Year in Review
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.
Dec 16, 2025 • 22min
Moving From EA to MCA? Watch Out for These Gotchas
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.
