The Directions on Microsoft Briefing

With more than 30 years of experience covering Microsoft, Directions on Microsoft (Directions) provides unique perspectives about the shifts in Microsoft technologies, roadmaps, and licensing policies that matter most to enterprise-size companies. Each month, industry veteran Mary Jo Foley interviews a different Directions analyst for informed insights and advice to help you drive full value from your Microsoft investments.
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Need a transcript of the episode? Please contact info@directionsonmicrosoft.com
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Season 2
Episode 8: Viva EXP - What you need to know about Microsoft's employee-experience platform
May 8, 2023
Microsoft's Viva employee-experience platform is a morphing collection of brand-new and older technologies aimed at improving workers' productivity and job satisfaction. Mary Jo Foley talks with Directions on Microsoft consultant Joshua Trupin about Viva's capabilities (including its AI capabilities), and how its packaging, pricing, and licensing are evolving.
Complementary report: Viva Services Promise Collaboration, Productivity
Episode 7: Microsoft EA Negotiation Podcast Series - Project Management
April 28, 2023
In this first installment of a multi-episode series covering Enterprise Agreements (EAs), Mary Jo Foley talks with Direction on Microsoft consultant Gus Volpe about EA negotiation project management -- why it's key to the EA negotiation process; the pillars of an effective EA project plan; and the top EA project management pitfalls to avoid.
Episode 6: Generative AI - Where Customers Need to Look Before They Leap
April 16, 2023
Generative AI is taking off in the enterprise, but there are many legal, governance, compliance, and privacy issues that customers need to consider first. Mary Jo Foley talks with Directions analyst Michael Cherry about some of the big-picture issues that organizations need to tackle before putting these new AI technologies into production.
Episode 5: Teams or Outlook? Why Not Both?
March 9, 2023
People forget, but Teams isn't Microsoft's only collaboration solution: Exchange combined with Outlook is by far Microsoft’s most mature and popular collaboration platform. In this episode, Mary Jo Foley talks with Directions' Rob Helm and Jim Gaynor about where Teams and Outlook overlap, integrate and compete -- and what it means for customers planning their collaboration strategies.
Episode 4: Microsoft Licensing for Non-Microsoft Clouds
March 1, 2023
Microsoft licensing rules are written to favor customers that use Azure and penalize customers who run their Microsoft software on competitors’ cloud platforms, especially AWS, Google, and Alibaba. In this podcast, Mary Jo Foley and analyst Wes Miller discuss the extra licensing costs Microsoft customers face when they use non-Microsoft clouds to run their Microsoft workloads – including recent and upcoming rule changes that further increase the pressure to use Azure.
Episode 3: Azure-Connected Features in SQL 2022
February 9, 2023
In this episode, Mary Jo Foley and analyst Andrew Snodgrass discuss the advantages and limitations of the new Azure-connected features in SQL Server 2022. They cover the new use scenarios the Azure-connected features enable, additional Azure service you’ll need to make them work, and how they may limit SQL Server 2022’s useful life. The episode concludes with thoughts on what increased Azure connectivity means for the future of SQL Server.
Episode 2: The World of Microsoft Regulatory Compliance Solutions
February 2, 2023
Regulatory compliance is a challenge for most large organizations. In this podcast, Mary Jo Foley and analyst Barry Briggs discuss the headaches regulatory compliance creates for IT departments and the “good news-bad news” of new cloud solutions Microsoft offers to help.
Episode 1: Analyzing Microsoft’s Migration to .NET
January 16, 2023
In this first episode of our second season, Mary Jo Foley and analyst Rob Sanfilippo discuss Microsoft’s case studies of its migration from the .NET Framework to .NET. What were the benefits gained and lessons learned, what is missing from Microsoft’s narratives, and under what circumstances is it best to migrate to .NET? Mary Jo and Rob also discuss the value of Microsoft case studies in general.
Complementary report: Lessons from Microsoft’s Internal .NET Upgrade
Meet your host, Mary Jo Foley

Mary Jo Foley is the Editor in Chief at Directions on Microsoft. Before joining Directions, Mary Jo was the Editor of the "All About Microsoft" blog on ZDNET. She also was the co-host of the "Windows Weekly" podcast on the TWiT Network. She has been a technology journalist for 35+ years and has focused on covering Microsoft exclusively for the majority of her career.
Season 1
Episode 13: Microsoft Teams: What’s Next for the platform?
December 16, 2022
In this episode of the Directions on Microsoft Briefing, Mary Jo Foley and analyst Jim Gaynor discuss recent Teams announcements, including what features are likely to launch, and which may not be generally available in the near future. They also discuss how to choose which Teams options are right for your organization as well as which new feature Directions’ customers mention wanting the most.
Complementary report: Teams Premium Enhances Meetings, for a Price
Episode 12: The Microsoft End-of-Life Meteor Approaches
November 17, 2022
In this episode of the Directions on Microsoft Briefing, Mary Jo Foley and Directions analysts Joshua Trupin and Rob Helm discuss upcoming end-of-life dates for Microsoft on-premises products that could catch many Microsoft customers by surprise. They also offer advice and guidance on how organizations can prepare to minimize the impact.
Complementary report: 2025 Support Meteor Leads to Software Mass Extinction
Episode 11: The Microsoft Cloud - Past, Present & Future
October 19, 2022
In this episode of the Directions on Microsoft Briefing, Mary Jo Foley and Directions analyst Barry Briggs discuss the uneven history of Microsoft’s cloud strategy, including what it got right and got wrong. They also discuss where the Microsoft Cloud is now headed and what that means for both its customers and competitors.
Episode 10: What Makes Microsoft Licensing So Hard? A Brief History
September 15, 2022
In this episode, Directions on Microsoft co-founder Rob Horwitz joins Mary-Jo Foley to discuss one of the biggest pain points for Microsoft enterprise customers: licensing. Rob explains why Microsoft licensing is mind-bogglingly complex and what makes compliance practically impossible. He also provides advice on how customers should approach their own Microsoft compliance challenges.
Complementary report: The Challenges of Licensing Shared Devices
Episode 09: Trusting Microsoft - Features, Updates, and Security
August 17, 2022
In this episode, Mary Jo Foley and Directions on Microsoft senior analyst Michael Cherry discuss who you should trust as speaking for Microsoft, and whether Windows 11 is the most secure version of Windows.
Complementary report: Lessons from Microsoft’s Windows 11 Upgrade
Episode 08: GitHub versus Azure DevOps: Is Panic Warranted?
July 25, 2022
GitHub has received major Microsoft investments since it was acquired. It is now a centerpiece of Microsoft’s developer platform. Directions on Microsoft analyst Rob Sanfilippo joins Mary-Jo Foley to discuss how GitHub will impact the future of Azure DevOps, how organizations can respond, and some new Azure services that organizational development teams should consider.
Complementary report: GitHub vs. Azure DevOps
Episode 07: Five Things You Need to Know About Power Platform
June 15, 2022
Power Platform, a set of low-code, easy to use development services from Microsoft are assuming a rapidly expanding role in many companies’ IT footprints. Directions on Microsoft analyst Joshua Trupin joins Mary-Jo Foley to discuss some of the licensing traps and complexities that every company needs to know about before adopting these services.
Complementary report: Preparing for Power Platform Usage Limit Enforcement
Episode 06: Negotiating a Microsoft EA
April 21, 2022
In this episode, Mary Jo Foley talks to Directions on Microsoft veteran negotiator Dean Bedwell about Microsoft Enterprise Agreements.
Complementary report: Executive Focus - Negotiating Microsoft Licensing Agreements
Episode 05: Windows on Macs
April 21, 2022
In this episode, Mary Jo Foley and Directions on Microsoft analyst Wes Miller talk about Windows on ARM, Apple silicon Macs, and the feasibility of using Windows on ARM running virtually on a modern Mac.
Complementary report: Mac Users Can Benefit from Microsoft 365
Episode 04: Microsoft’s future for Windows Server
March 17, 2022
In this episode, Mary Jo Foley and Directions on Microsoft analyst Jim Gaynor talk about Windows Server 2022, Windows Server Azure Edition, Azure Stack HCI, and the future of Microsoft’s server operating systems both on-premises and in the cloud.
Complementary report: Microsoft’s Server OS Strategy Pushes Customers to Azure
Episode 03: Power BI - Beyond Pretty Pictures
February 18, 2022
In this episode, Mary Jo Foley and Directions on Microsoft analyst Andrew Snodgrass discuss key Power BI capabilities, likely future improvements, and the licensing and deployment challenges facing customers who use it.
Complementary report: Choosing Power BI - Part 1. Platforms and Decision Process
Episode 02: Meet the Founders
February 7, 2022
In this episode, Mary Jo Foley chats with Directions on Microsoft founders Rob Horwitz and Jeff Parker who started their company 30 years ago.
Downloadable pdf: Directions' mission and services
Episode 01: Microsoft's Strategy for 2022 - It's All About the Cloud
January 31, 2022
In this episode, Mary Jo Foley talks with Directions on Microsoft analyst Barry Briggs about where Microsoft is headed in the next 12 months, and it's straight into the cloud.
Complementary report: Executive Focus - Understanding Microsoft’s Multiple Clouds