The Directions on Microsoft Briefing Podcast

Latest Episodes:

Microsoft Licensing and Negotiation: A Year in Review Dec 22, 2025

Show notes

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.

Moving From EA to MCA? Watch Out for These Gotchas Dec 16, 2025

Show notes

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.

Is Cloud Computing Becoming a Commodity? Dec 10, 2025

Show notes

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.

Microsoft's Extended Security Updates: What You Need to Know Oct 29, 2025

Show notes

Cost isn't the only consideration when it comes to deploying ESUs. Directions on Microsoft analysts Jim Gaynor and Rob Helm share guidance on migration, negotiation, and governance and other implications of ESUs with Mary Jo Foley.

What's Happening with Microsoft Exchange? Oct 17, 2025

Show notes

There's been lots going on with Exchange lately, ranging from feature retirements, to AI and security infusions, to a new subscription edition. Catch up on all the latest in this episode with special guest MVP and Redmond & Associates founder Tony Redmond, Directions analyst Rob Helm and Mary Jo Foley.

Microsoft Contract Negotiation: Escalation Dos and Don'ts Sep 19, 2025

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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.

Enterprise Copilot Adoption: Lessons from the Field Sep 08, 2025

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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.

Get Ready for Microsoft's Coming Licensing Changes Aug 26, 2025

Show notes

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.

Is No-Code Really Dead? Aug 08, 2025

Show notes

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.

The Human Side of Data Governance Jul 16, 2025

Show notes

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.