The Directions on Microsoft Briefing Podcast

Directions on Microsoft
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Sep 19, 2025 • 22min

Microsoft Contract Negotiation: Escalation Dos and Don'ts

Organizations need to weigh when, how, and if it's worth escalating during their Microsoft contract negotiation process. In this episode, Directions on Microsoft Senior Consultant Steve Kelley shares his dos, don'ts, (and a few war stories) with Mary Jo Foley.
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Sep 8, 2025 • 31min

Enterprise Copilot Adoption: Lessons from the Field 

PwC Principal James Farhat joins Directions analyst Barry Briggs and Mary Jo Foley to discuss early real-world wins and challenges around Microsoft 365 Copilot adoption.
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Aug 26, 2025 • 19min

Get Ready for Microsoft's Coming Licensing Changes

Starting Nov. 1, Microsoft is dropping the programmatic discounts that were baked into its volume-licensing agreements. But price hikes are just one of the resulting fallouts for which enterprises need to prepare immediately, as Directions' lead negotiator Dean Bedwell details in this episode with Mary Jo Foley.
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Aug 8, 2025 • 23min

Is No-Code Really Dead?

Is there still a place for no/low-code tools like those in Microsoft's Power Platform with the rise of generative AI and GitHub Copilot? The New Stack's news editor Darryl Taft joins Directions Rob Sanfilippo and Mary Jo Foley to debate the topic.
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Jul 16, 2025 • 24min

The Human Side of Data Governance

We've all heard repeatedly about the importance of securing your data estate before implementing Copilots, agents and other AI components. Directions analyst Barry Briggs talks with Mary Jo Foley about what needs to happen among execs, IT and employees on for data governance to really work.
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Jun 26, 2025 • 36min

SQL Server 2025 to Deliver AI Features and Lots More

Microsoft is set to release this fall SQL Server 2025, its first new version of its flagship database in three years. Special guest, Microsoft Regional Director and MVP Andrew Brust and Directions analyst Andrew Snodgrass detail the AI, performance and other top SQL Server 2025 features in this episode with Mary Jo Foley.
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Jun 10, 2025 • 32min

Microsoft Security Copilot: What You Need to Know

Microsoft made Security Copilot generally available just over a year ago. Special guest Microsoft MVP Ru Campbell and Directions analyst Wes Miller talk with Mary Jo Foley about the ways this marquee copilot is evolving, in terms of packaging, pricing and licensing — and what customers interested in it should and shouldn't be doing.
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May 29, 2025 • 23min

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).
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May 21, 2025 • 23min

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.
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9 snips
May 1, 2025 • 49min

Microsoft: A Look Back From Inside

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.

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