The Directions on Microsoft Briefing Podcast
by Directions on Microsoft
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On the show
From 15 epsHosts
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Recent episodes
How the Changing Cyber Landscape Affects Your Org
Aug 27, 2026
Unknown duration
Microsoft's FY27: What Enterprises Need to Know
Jul 9, 2026
30m 00s
What You Need to Know Before You Sign a Microsoft MEO
Jun 25, 2026
26m 00s
Microsoft's Evolving AI Strategy: New Clues from Build
Jun 11, 2026
27m 00s
Three Smart Guys: Too Big to Flail?
Jun 11, 2026
45m 00s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 8/27/26 | How the Changing Cyber Landscape Affects Your Org | 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. | — | ||||||
| 7/9/26 | enterprise pricinglicensing hurdles+3 | Mary Jo Foley | Microsoft | — | MicrosoftFY27+4 | — | 30m 00s | ||
| 6/25/26 | Microsoft MEOMultiple Equivalent Offer+3 | Steve Kelley | Microsoft MEODirections on Microsoft | — | Microsoft MEOMultiple Equivalent Offer+4 | — | 26m 00s | ||
| 6/11/26 | AI strategyMicrosoft Build+4 | David Berry | Microsoft | — | MicrosoftAI strategy+5 | — | 27m 00s | ||
| 6/11/26 | computing architectureintelligent client+1 | George GilbertPeter O'Kelly | Directions on Microsoft | — | computing architectureintelligent client+4 | — | 45m 00s | ||
| 5/21/26 | Azure consumptionM365 costs+3 | Lane Shelton | AzureM365+1 | — | AzureM365+3 | — | 21m 00s | ||
| 4/23/26 | Microsoft 365Agent 365+3 | Lane Shelton | Microsoft 365 E7Agent 365 | — | Microsoft 365 E7Agent 365+3 | — | 21m 00s | ||
| 4/15/26 | AIcollaboration software+3 | — | Directions on Microsoft | — | AIcollaboration+3 | — | 34m 00s | ||
| 4/9/26 | digital sovereigntyMicrosoft offerings+3 | Greg DeMichillie | Microsoft | — | digital sovereigntyMicrosoft+5 | — | 23m 00s | ||
| 4/2/26 | Enterprise Agreementrenewal strategies+3 | Lane Shelton | Directions on Microsoft | — | Enterprise Agreementrenewal+3 | — | 28m 00s | ||
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| 3/26/26 | AIMicrosoft Office+3 | George GilbertPeter O'Kelly | OfficeAI+1 | — | MicrosoftOffice+6 | — | 34m 00s | ||
| 3/12/26 | M365 E7Microsoft+4 | Lane Shelton | M365 E7Directions on Microsoft | — | M365 E7Microsoft+5 | — | 25m 00s | ||
| 3/4/26 | AIdata+3 | George GilbertPeter O'Kelly | Microsoft | — | AIdata+3 | — | 33m 00s | ||
| 2/19/26 | Microsoft 365Copilot licensing+3 | Mary Jo Foley | Microsoft 365 CopilotDirections on Microsoft | — | Microsoft 365Copilot+3 | — | 37m 00s | ||
| 2/12/26 | SQL Servermigrations+3 | Andrew Snodgrass | SQL Server 2016SQL Server 2017 | — | SQL Servermigrations+3 | — | 25m 00s | ||
| 1/29/26 | MicrosoftAI strategies+3 | George GilbertPeter O'Kelly | Microsoft | — | MicrosoftAI+4 | — | 30m 00s | ||
| 1/23/26 | Microsoft 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. | — | ||||||
| 1/8/26 | 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. | — | ||||||
| 12/22/25 | 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. | — | ||||||
| 12/16/25 | 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. | — | ||||||
| 12/10/25 | 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. | — | ||||||
| 10/29/25 | 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. | — | ||||||
| 10/17/25 | 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. | — | ||||||
| 9/19/25 | 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. | — | ||||||
| 9/8/25 | 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. | — | ||||||
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