The Directions on Microsoft Briefing Podcast
Directions on Microsoft
Show overview
The Directions on Microsoft Briefing Podcast launched in 2025 and has put out 45 episodes in the time since. That works out to roughly 25 hours of audio in total. Releases follow a fortnightly cadence, with the show now in its 5th season.
Episodes typically run twenty to thirty-five minutes — most land between 23 min and 35 min — though episode length varies meaningfully from one episode to the next. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-US-language Technology show.
The show is actively publishing — the most recent episode landed 5 days ago, with 15 episodes already out so far this year. Published by Directions on Microsoft.
From the publisher
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.
Latest Episodes
View all 45 episodesMicrosoft's Evolving AI Strategy: New Clues from Build
Three Smart Guys: Too Big to Flail?
Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs
Microsoft 365 E7: Ready Or Not, Here It Comes
Three Smart Guys: Can AI Save Collaboration Software?
S5 Ep 7Thinking Realistically About Digital Sovereignty
Microsoft has several digital sovereignty offerings, but are they right -- and realistic -- for your org? Directions' analyst Greg DeMichillie shares his thoughts with Mary Jo Foley.
S5 Ep 6Tips and Tricks For Your Next EA Renewal
It is possible to make your next Enterprise Agreement renewal less painful and more advantageous to your org. Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley key strategies that can help.
S1 Ep 3Three 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.
S5 Ep 5What 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.
S1 Ep 2Three 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.
S5 Ep 4Microsoft 365 Copilot Licensing: Five Things You Need to Know
Whether you're still on the fence or in the midst of deploying Microsoft 365 Copilot, you'll want to make sure you know these five things about M365 Copilot licensing. Directions' Rob Horwitz digs into the details with Mary Jo Foley in this episode.
S5 Ep 3SQL 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.
S1 Ep 1Three 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.
S5 Ep 2Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
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.
S5 Ep 1What 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.
S4 Ep 21Microsoft 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.
S4 Ep 20Moving 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.
S4 Ep 19Is 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.
S4 Ep 18Microsoft'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.
S4 Ep 17What'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.