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
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.
Dec 10, 2025 • 22min
Is Cloud Computing Becoming a Commodity?
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.
Oct 29, 2025 • 22min
Microsoft's Extended Security Updates: What You Need to Know
Cost isn't the only consideration when it comes to deploying ESUs. Directions on Microsoft analysts Jim Gaynor and Rob Helm share guidance on migration, negotiation, and governance and other implications of ESUs with Mary Jo Foley.
Oct 17, 2025 • 47min
What's Happening with Microsoft Exchange?
There's been lots going on with Exchange lately, ranging from feature retirements, to AI and security infusions, to a new subscription edition. Catch up on all the latest in this episode with special guest MVP and Redmond & Associates founder Tony Redmond, Directions analyst Rob Helm and Mary Jo Foley.
Sep 19, 2025 • 22min
Microsoft Contract Negotiation: Escalation Dos and Don'ts
Organizations need to weigh when, how, and if it's worth escalating during their Microsoft contract negotiation process. In this episode, Directions on Microsoft Senior Consultant Steve Kelley shares his dos, don'ts, (and a few war stories) with Mary Jo Foley.
Sep 8, 2025 • 31min
Enterprise Copilot Adoption: Lessons from the Field
PwC Principal James Farhat joins Directions analyst Barry Briggs and Mary Jo Foley to discuss early real-world wins and challenges around Microsoft 365 Copilot adoption.
