The Directions on Microsoft Briefing Podcast

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  Uncovering the Hidden Costs of M365 Copilot 17.09.2026 29min

  Cowork consumption costs are just the tip of the iceberg when it comes to rapidly expanding M365 Copilot costs. Directions analyst David Berry lays out the potential gotchas in this episode with Mary Jo Foley.
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  How and Why We Built an AI Assistant 10.09.2026 29min

  Directions on Microsoft built its own AI Assistant to help with Microsoft technology and licensing queries. Analysts Barry Briggs and Andrew Snodgrass share experiences and lessons learned with Mary Jo Foley.
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  How the Changing Cyber Landscape Affects Your Org 27.08.2026 20min

  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.
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  Microsoft's FY27: What Enterprises Need to Know 09.07.2026 30min

  Microsoft has established some high enterprise pricing and licensing hurdles going into its FY27. Directions' Advisory Services Director Lane Shelton talks with Mary Jo Foley about the obstacles and potential opportunities.
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  What You Need to Know Before You Sign a Microsoft MEO 25.06.2026 26min

  The Multiple Equivalent Offer is not the deal it may seem. Directions' analyst Steve Kelley shares tips with Mary Jo Foley to help orgs make a MEO work more to their advantage.
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  Microsoft's Evolving AI Strategy: New Clues from Build 11.06.2026 27min

  Directions analyst David Berry sifts through the AI strategy announcements from Microsoft Build and discusses with Mary Jo Foley the potential impact on enterprises customers.
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  Three Smart Guys: Too Big to Flail? 11.06.2026 45min

  Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly outline the implications of a new computing architecture anchored by an intelligent client.
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  Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs 21.05.2026 21min

  Are you being hit with Azure consumption constraints and/or skyrocketing M365 costs in your Azure bill? Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley his tips and advice on how to handle these issues.
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  Microsoft 365 E7: Ready Or Not, Here It Comes 23.04.2026 21min

  Microsoft is launching E7 and Agent 365 on May 1. Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley the latest on what customers should know before they dive in.
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  Three Smart Guys: Can AI Save Collaboration Software? 15.04.2026 34min

  After decades of incremental change, collaboration software is at an inflection point, and AI could have a big influence on where it goes next, as the 'Three Smart Guys' team discusses.
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  Thinking Realistically About Digital Sovereignty 09.04.2026 23min

  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.
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  Tips and Tricks For Your Next EA Renewal 02.04.2026 28min

  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.
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  Three Smart Guys: Is Office Dead? 26.03.2026 34min

  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.
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  What We Know (and Don't) About M365 E7 12.03.2026 25min

  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.
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  Three Smart Guys: It's All About the Data 04.03.2026 33min

  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.
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  Microsoft 365 Copilot Licensing: Five Things You Need to Know 19.02.2026 37min

  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.
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  SQL Server Migrations: Tips to Help You Prepare 12.02.2026 25min

  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.
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  Three Smart Guys: Microsoft's 2026 Challenges 29.01.2026 30min

  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.
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  Microsoft Ignoring Your Org's Needs? We Have Some Tips for That 23.01.2026 24min

  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.
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  What Microsoft's Recent M365 Bundling Moves Mean for You 08.01.2026 17min

  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.