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.

May 29, 2025 . Season – 4 · Episode – 9 · Duration – 23m Microsoft 365 Copilot Chat vs. OpenAI's ChatGPT: How to Choose So many AI chat products; so little time. Directions on Microsoft's newest analyst David Berry shares his insights with Mary Jo Foley on how enterprise customers should evaluate Microsoft 365 Copilot Chat vs. ChatGPT (and Microsoft 365 Copilot itself).

May 21, 2025 . Season – 4 · Episode – 8 · Duration – 23m What's Going on With Windows With less than six months left until Windows 10 is no longer supported by Microsoft, Windows users have a lot of uncertainties and a rapidly evolving landscape to navigate. Directions analyst Wes Miller and Mary Jo Foley talk about what — and what not — to expect in the coming months.

Updated: May 1, 2025 . Season – 4 · Episode – 7 · Duration – 49m Microsoft: A Look Back From Inside This year marks Microsoft's 50th anniversary and several of the Directions analysts were part of the company's history. Barry Briggs, Michael Cherry, and Rob Sanfilippo share some ringside-seat insights with Mary Jo Foley from their years working across different teams and times at Microsoft.

March 28, 2025 . Season – 4 · Episode – 6 · Duration – 33m Understanding Microsoft's AI Strategy Microsoft's repositioning of itself as an AI company has major implications for customers in terms of how you plan, buy, license and manage Microsoft products. Directions analyst Barry Briggs discusses with Mary Jo Foley what enterprises really need to know about Microsoft's AI strategy.