The Directions on Microsoft Briefing Podcast
Technology Podcasts
With more than 30 years of experience covering Microsoft, Directions on Microsoft provides unique perspectives about the shifts in Microsoft technologies, roadmaps and licensing policies that matter most to enterprise-size companies. Twice each month industry veteran Mary Jo Foley interviews a different Directions analyst for informed insights and advice to help you derive full value from your Microsoft investments.
Location:
United States
Genres:
Technology Podcasts
Description:
With more than 30 years of experience covering Microsoft, Directions on Microsoft provides unique perspectives about the shifts in Microsoft technologies, roadmaps and licensing policies that matter most to enterprise-size companies. Twice each month industry veteran Mary Jo Foley interviews a different Directions analyst for informed insights and advice to help you derive full value from your Microsoft investments.
Language:
English
Contact:
206-755-0408
Episodes
Microsoft 365 Copilot Licensing: Five Things You Need to Know
2/19/2026
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.
Duration:00:37:00
SQL Server Migrations: Tips to Help You Prepare
2/12/2026
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.
Duration:00:25:00
Three Smart Guys: Microsoft's 2026 Challenges
1/29/2026
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.
Duration:00:30:00
Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
1/23/2026
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.
Duration:00:24:00
What Microsoft's Recent M365 Bundling Moves Mean for You
1/8/2026
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.
Duration:00:17:00
Microsoft Licensing and Negotiation: A Year in Review
12/22/2025
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.
Duration:00:20:00
Moving From EA to MCA? Watch Out for These Gotchas
12/16/2025
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.
Duration:00:22:00
Is Cloud Computing Becoming a Commodity?
12/10/2025
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.
Duration:00:22:00
Microsoft's Extended Security Updates: What You Need to Know
10/29/2025
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.
Duration:00:22:00
What's Happening with Microsoft Exchange?
10/17/2025
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.
Duration:00:47:00
Microsoft Contract Negotiation: Escalation Dos and Don'ts
9/19/2025
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.
Duration:00:22:00
Enterprise Copilot Adoption: Lessons from the Field
9/8/2025
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.
Duration:00:31:00
Get Ready for Microsoft's Coming Licensing Changes
8/26/2025
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.
Duration:00:19:00
Is No-Code Really Dead?
8/8/2025
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.
Duration:00:23:00
The Human Side of Data Governance
7/16/2025
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.
Duration:00:24:00
SQL Server 2025 to Deliver AI Features and Lots More
6/26/2025
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.
Duration:00:36:00
Microsoft Security Copilot: What You Need to Know
6/10/2025
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.
Duration:00:32:00
Microsoft 365 Copilot Chat vs. OpenAI's ChatGPT: How to Choose
5/29/2025
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).
Duration:00:23:00
What's Going on With Windows
5/21/2025
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.
Duration:00:23:00
Microsoft: A Look Back From Inside
5/1/2025
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.
Duration:00:49:00