Podcasts

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.

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September 17, 2026 . Season – 5 · Episode – 15 · Duration – 29m Uncovering the Hidden Costs of M365 Copilot 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.

September 10, 2026 . Season – 5 · Episode – 14 · Duration – 29m How and Why We Built an AI Assistant 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.

August 27, 2026 . Season – 5 · Episode – 13 · Duration – 20m 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.

July 9, 2026 . Season – 5 · Episode – 12 · Duration – 30m Microsoft's FY27: What Enterprises Need to Know 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.