The Directions on Microsoft Briefing Podcast

Directions on Microsoft · directionsonmicrosoft.com

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.

40 episodes

1mo ago latest

fortnightly cadence

English language

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Episodes 40

How the Changing Cyber Landscape Affects Your Org
3d ago · 20:00
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
1mo ago · 30:00
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
2mo ago · 26:00
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
2mo ago · 27:00
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?
2mo ago · 45:00
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
3mo ago · 21:00
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
4mo ago · 21:00
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?
4mo ago · 34:00
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
4mo ago · 23:00
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
5mo ago · 28:00
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?
5mo ago · 34:00
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
5mo ago · 25:00
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
5mo ago · 33:00
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
6mo ago · 37:00
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
6mo ago · 25:00
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
7mo ago · 30:00
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
7mo ago · 24:00
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
7mo ago · 17:00
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
8mo ago · 20:00
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
8mo ago · 22:00
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?
8mo ago · 22:00
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
10mo ago · 22:00
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?
10mo ago · 47:00
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
11mo ago · 22:00
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
11mo ago · 31:00
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.

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The Directions on Microsoft Briefing Podcast

Episodes 40

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What You Need to Know Before You Sign a Microsoft MEO

Microsoft's Evolving AI Strategy: New Clues from Build

Three Smart Guys: Too Big to Flail?

Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs

Microsoft 365 E7: Ready Or Not, Here It Comes

Three Smart Guys: Can AI Save Collaboration Software?

Thinking Realistically About Digital Sovereignty

Tips and Tricks For Your Next EA Renewal

Three Smart Guys: Is Office Dead?

What We Know (and Don't) About M365 E7

Three Smart Guys: It's All About the Data

Microsoft 365 Copilot Licensing: Five Things You Need to Know

SQL Server Migrations: Tips to Help You Prepare

Three Smart Guys: Microsoft's 2026 Challenges

Microsoft Ignoring Your Org's Needs? We Have Some Tips for That

What Microsoft's Recent M365 Bundling Moves Mean for You

Microsoft Licensing and Negotiation: A Year in Review

Moving From EA to MCA? Watch Out for These Gotchas

Is Cloud Computing Becoming a Commodity?

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Episodes 40

How the Changing Cyber Landscape Affects Your Org

Microsoft's FY27: What Enterprises Need to Know

What You Need to Know Before You Sign a Microsoft MEO

Microsoft's Evolving AI Strategy: New Clues from Build

Three Smart Guys: Too Big to Flail?

Tips for Dealing with Azure Consumption Constraints and Hidden M365 Costs

Microsoft 365 E7: Ready Or Not, Here It Comes

Three Smart Guys: Can AI Save Collaboration Software?

Thinking Realistically About Digital Sovereignty

Tips and Tricks For Your Next EA Renewal

Three Smart Guys: Is Office Dead?

What We Know (and Don't) About M365 E7

Three Smart Guys: It's All About the Data

Microsoft 365 Copilot Licensing: Five Things You Need to Know

SQL Server Migrations: Tips to Help You Prepare

Three Smart Guys: Microsoft's 2026 Challenges

Microsoft Ignoring Your Org's Needs? We Have Some Tips for That

What Microsoft's Recent M365 Bundling Moves Mean for You

Microsoft Licensing and Negotiation: A Year in Review

Moving From EA to MCA? Watch Out for These Gotchas

Is Cloud Computing Becoming a Commodity?

Microsoft's Extended Security Updates: What You Need to Know

What's Happening with Microsoft Exchange?

Microsoft Contract Negotiation: Escalation Dos and Don'ts

Enterprise Copilot Adoption: Lessons from the Field