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The Directions on Microsoft Briefing Podcast

by Directions on Microsoft
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Latest episodes

  • What Are Microsoft Enterprise Customers Thinking?

    October 1, 2026 · 29 min

    Microsoft enterprise customers have a lot on their minds. At Directions' latest Licensing Bootcamp, we got an earful. Analyst Wes Miller tells Mary Jo Foley all about it.

  • Uncovering the Hidden Costs of M365 Copilot

    September 17, 2026 · 29 min

    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.

  • How and Why We Built an AI Assistant

    September 10, 2026 · 29 min

    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.

  • How the Changing Cyber Landscape Affects Your Org

    August 27, 2026 · 20 min

    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…

  • Microsoft's FY27: What Enterprises Need to Know

    July 9, 2026 · 30 min

    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

    June 25, 2026 · 26 min

    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.

  • Microsoft's Evolving AI Strategy: New Clues from Build

    June 11, 2026 · 27 min

    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.

  • Three Smart Guys: Too Big to Flail?

    June 11, 2026 · 45 min

    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.

  • Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs

    May 21, 2026 · 21 min

    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.

  • Microsoft 365 E7: Ready Or Not, Here It Comes

    April 23, 2026 · 21 min

    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.

  • Three Smart Guys: Can AI Save Collaboration Software?

    April 15, 2026 · 34 min

    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.

  • Thinking Realistically About Digital Sovereignty

    April 9, 2026 · 23 min

    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.

Full episode archive on Apple Podcasts →

About the show

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.