The Directions on Microsoft Briefing Podcast
Directions on Microsoft is a research firm with more than 30 years of experience covering Microsoft. The Directions on Microsoft Briefing Podcast provides unique perspectives on shifts in Microsoft technologies, roadmaps, and licensing policies that matter to enterprise-size companies. Twice each month, industry veteran Mary Jo Foley interviews a different Directions analyst for informed insights. The show offers advice to help organizations derive full value from their Microsoft investments.
Episodes
What Are Microsoft Enterprise Customers Thinking?
Microsoft enterprise customers have a lot on their minds. At Directions' latest Licensing Bootcamp, we got an earful. Analyst Wes Miller tells Mary Jo Foley all about it.
Uncovering the Hidden Costs of M365 Copilot
Cowork consumption costs are just the tip of the iceberg when it comes to rapidly expanding M365 Copilot costs. Directions analyst David Berry lays out the potential gotchas in this episode with Mary Jo Foley.
How and Why We Built an AI Assistant
Directions on Microsoft built its own AI Assistant to help with Microsoft technology and licensing queries. Analysts Barry Briggs and Andrew Snodgrass share experiences and lessons learned with Mary Jo Foley.
How the Changing Cyber Landscape Affects Your Org
The cybersecurity landscape is changing rapidly thanks to AI and other shifting dynamics. Directions on Microsoft Advisor Kathryn Mihalich shares her tips with Mary Jo Foley on what executives need to know to make the best technology and licensing decisions.
Microsoft's FY27: What Enterprises Need to Know
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.
What You Need to Know Before You Sign a Microsoft MEO
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.
Microsoft's Evolving AI Strategy: New Clues from Build
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.
Three Smart Guys: Too Big to Flail?
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.
Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs
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 365 E7: Ready Or Not, Here It Comes
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.
Three Smart Guys: Can AI Save Collaboration Software?
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.
Thinking Realistically About Digital Sovereignty
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.
Tips and Tricks For Your Next EA Renewal
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.
Three Smart Guys: Is Office Dead?
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.
What We Know (and Don't) About M365 E7
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.
Three Smart Guys: It's All About the Data
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.
Microsoft 365 Copilot Licensing: Five Things You Need to Know
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 Migrations: Tips to Help You Prepare
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.
Three Smart Guys: Microsoft's 2026 Challenges
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 Ignoring Your Org's Needs? We Have Some Tips for That
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.
What Microsoft's Recent M365 Bundling Moves Mean for You
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.
Microsoft Licensing and Negotiation: A Year in Review
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
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?
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
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?
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
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
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
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?
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
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.
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.
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.
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).
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.
Microsoft: A Look Back From Inside
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.
Understanding Microsoft's AI Strategy
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.
The Growing Risks of Staying On-Premises
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.
The New Face of Shadow IT: A Directions on Microsoft Brainstorm
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.
How to Save Money with Azure Reservations
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.
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