The Directions on Microsoft Briefing Podcast

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.

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.

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.

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.

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.

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.

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.

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.

Microsoft's Azure Local falls in the uncanny valley between on-prem and cloud. Our newest analyst Greg DeMichillie shares his recommendations with Mary Jo Foley on what customers should (and shouldn't yet) do with 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.

Microsoft's Ignite 2024 conference focused heavily on all things AI. But that wasn't all. Directions analyst Wes Miller grills Mary Jo Foley about the announcements and non-announcements from Chicago.

Microsoft's intense focus on all things AI has resulted in noticeable security, quality and delivery issues with some of its key enterprise products and services. Directions analysts Jim Gaynor and Wes Miller share with Mary Jo Foley their insights on how Microsoft's new priorities have affected and may continue to impact its commercial customers.

There's one year left before Microsoft ends support for Windows 10. Directions analysts Michael Cherry, Jim Gaynor, and Wes Miller talk with Mary Jo Foley about the best paths forward for enterprises who want to stay safe and up-to-date.

CxOs are juggling more than just AI ROI these days. Security, cloud-computing costs, governance and more all are vying for attention and budgets. Directions analyst Barry Briggs and Mary Jo Foley talk about the latest technologies on which CxOs need to focus.

Microsoft is making more and more Dynamics 365 features available exclusively as part of pricey premium subscriptions. Directions analyst Andrew Snodgrass and Mary Jo Foley talk through the implications of this shift for customers both now and in the longer term.

As Microsoft commences its 'Wave 2' Copilot push, it's becoming more challenging than ever to find clear answers about features, pricing and licensing. Fortunately, Directions analyst Wes Miller and Mary Jo Foley have you covered with tips and resources to help with your evaluation of the growing family of Microsoft Copilots.

When it comes to databases, Microsoft offers almost too many options for storing and analyzing all kinds of data. Directions analysts Barry Briggs, Rob Sanfilippo and Andrew Snodgrass talk with Mary Jo Foley about how customers can keep up with the growing set of Microsoft on-premises and cloud database offerings and figure out which solution best fits their particular needs.