The Directions on Microsoft Briefing Podcast

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).

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.

Join Michael Cherry, a Directions analyst and Microsoft veteran since 1990 who’s set to retire, Rob Sanfilippo, a former Exchange Server team member, and Barry Briggs, ex-Lotus employee, as they reflect on Microsoft's remarkable 50-year journey. They unravel personal anecdotes from their time navigating tech challenges at major events, explore the evolving leadership under Gates, Ballmer, and Nadella, and share humorous insights from the company's dynamic culture. It's a nostalgic look at tech triumphs and transformative moments in Microsoft’s history.

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.

While some customers just cannot let go of their on-premises Microsoft products -- for legitimate and not-so-valid reasons -- the risks of running software on-prem are growing. Directions analyst Andrew Snodgrass talks with Mary Jo Foley about on-premises realities and provides some recommendations.

Whether you appreciate it, tolerate it, or want to stamp it out, Shadow IT is not going anywhere. Is this necessarily a bad thing? Directions analysts Barry Briggs, Greg DeMichillie and Rob Sanfilippo share with Mary Jo Foley their ideas for managing and channeling Shadow IT in this roundtable discussion.

Azure Reservations is one of the best ways enterprises can save money on their Microsoft contracts. But, as Directions' Wes Miller explains to Mary Jo Foley, you need to know the gotchas before you jump in.

Microsoft's Unified Support plan is not beloved by many enterprises. US Cloud VP Mike Jones provides the latest on the plan, plus some support tips and tricks in this conversation with Directions' Mary Jo Foley.

Greg DeMichillie, a data and infrastructure analyst at Directions on Microsoft, shares his insights on Azure Local, a hybrid solution that straddles the line between cloud and on-prem technology. He discusses the evolution of Microsoft's relationship with customers, highlighting significant shifts over the years. The conversation dives into the complexities of Azure Local, including integration challenges compared to competitors like AWS and Oracle. Greg also emphasizes innovative licensing strategies and the importance of historical data for businesses looking to leverage this technology.

Our panel of Directions on Microsoft analysts talk about the biggest Microsoft enterprise pain points for 2024 and predict what will be top-of-mind in 2025 in this recording of our annual update webinar.