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  • Microsoft 365 Copilot Licensing: Five Things You Need to Know

    Microsoft 365 Copilot Licensing: Five Things You Need to Know
    Feb 19 2026
    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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    37 Min.
  • SQL Server Migrations: Tips to Help You Prepare

    SQL Server Migrations: Tips to Help You Prepare
    Feb 12 2026
    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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    25 Min.
  • Three Smart Guys: Microsoft's 2026 Challenges

    Three Smart Guys: Microsoft's 2026 Challenges
    Jan 29 2026
    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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    30 Min.
  • Microsoft Ignoring Your Org's Needs? We Have Some Tips for That

    Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
    Jan 23 2026
    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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    24 Min.
  • What Microsoft's Recent M365 Bundling Moves Mean for You

    What Microsoft's Recent M365 Bundling Moves Mean for You
    Jan 8 2026
    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.
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    17 Min.
  • Microsoft Licensing and Negotiation: A Year in Review

    Microsoft Licensing and Negotiation: A Year in Review
    Dec 22 2025
    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.
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    20 Min.
  • Moving From EA to MCA? Watch Out for These Gotchas

    Moving From EA to MCA? Watch Out for These Gotchas
    Dec 16 2025
    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.
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    22 Min.
  • Is Cloud Computing Becoming a Commodity?

    Is Cloud Computing Becoming a Commodity?
    Dec 10 2025
    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.
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    22 Min.