The Directions on Microsoft Briefing Podcast

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.

The Multiple Equivalent Offer is not the deal it may seem. Directions' analyst Steve Kelley shares tips with Mary Jo Foley to help orgs make a MEO work more to their advantage.

Directions analyst David Berry sifts through the AI strategy announcements from Microsoft Build and discusses with Mary Jo Foley the potential impact on enterprises customers.

Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly outline the implications of a new computing architecture anchored by an intelligent client.

Are you being hit with Azure consumption constraints and/or skyrocketing M365 costs in your Azure bill? Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley his tips and advice on how to handle these issues.

Microsoft is launching E7 and Agent 365 on May 1. Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley the latest on what customers should know before they dive in.

After decades of incremental change, collaboration software is at an inflection point, and AI could have a big influence on where it goes next, as the 'Three Smart Guys' team discusses.

Microsoft has several digital sovereignty offerings, but are they right -- and realistic -- for your org? Directions' analyst Greg DeMichillie shares his thoughts with Mary Jo Foley.

It is possible to make your next Enterprise Agreement renewal less painful and more advantageous to your org. Directions' Advisory Services Director Lane Shelton shares with Mary Jo Foley key strategies that can help.

Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly discuss if and how AI could be making Microsoft's core Office apps more replaceable.

Beyond the known price tag and release date, there are still a lot of E7 unknowns. Directions' Advisory Services Director Lane Shelton shares his E7 educated guesses and customer advice with Mary Jo Foley.

Directions' Barry Briggs and industry analysts George Gilbert and Peter O'Kelly discuss how AI’s dependence on data is reshaping Microsoft’s enterprise strategy.

Whether you're still on the fence or in the midst of deploying Microsoft 365 Copilot, you'll want to make sure you know these five things about M365 Copilot licensing. Directions' Rob Horwitz digs into the details with Mary Jo Foley in this episode.

SQL Server 2016 and 2017 are leaving Extended support in the not-too-distant future. Directions' analyst Andrew Snodgrass shares his preparation checklist in this episode with Mary Jo Foley.

In this inaugural episode of the TSG podcast, Directions' Barry Briggs, along with industry analysts George Gilbert and Peter O'Kelly, discuss Microsoft's strategies in AI and beyond for 2026.

Microsoft's one-pointed AI focus may be clouding what your company really wants and needs. Directions analyst Jim Gaynor shares with Mary Jo Foley some ideas for fighting back.

Microsoft is bundling more separately priced features with Microsoft 365 SKUs, making the imminent inevitability of an E7 less likely. Directions analyst Wes Miller talks through the details and customer impact with Mary Jo Foley.

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.

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.

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.

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.

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.

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.

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. 

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.