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The Directions on Microsoft Briefing Podcast

Directions on Microsoft
Microsoft
Azure
Microsoft Enterprise Agreements
Microsoft 365
Negotiation Phases
Dynamics 365
Microsoft Enterprise Agreement
Microsoft Licensing
License Optimization
Negotiation Planning
Openai
Copilot
Software Assurance
Microsoft Teams
SWOT Analysis
Negotiation Strategies
Chatgpt
Licensing Strategies
Windows 11
Windows 365

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 Mic... more

PublishesTwice monthlyEpisodes61Founded4 years ago
Number of ListenersCategory
Technology

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Artwork for The Directions on Microsoft Briefing Podcast

Latest Episodes

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.

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Recent Guests

Andrew Snodgrass
Directions Analyst specializing in Microsoft's data management and business intelligence solutions
Directions on Microsoft
Episode: SQL Server Migrations: Tips to Help You Prepare
Jim Gaynor
Analyst at Directions on Microsoft, leads the editorial team
Directions on Microsoft
Episode: Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
Dean Bedwell
Licensing expert and negotiator at Directions on Microsoft
Directions on Microsoft
Episode: Moving From EA to MCA? Watch Out for These Gotchas
Tony Redmond
Lead author for the Office 365 for IT Pro's eBook and Principal of Redmond & Associates
Redmond & Associates
Episode: What's Happening with Microsoft Exchange?
Rob Helm
Managing Vice President at Directions
Directions on Microsoft
Episode: What's Happening with Microsoft Exchange?
Steve Kelley
Negotiation expert specializing in Microsoft licensing agreements
Directions on Microsoft
Episode: Microsoft Contract Negotiation: Escalation Dos and Don'ts
Darryl Taft
News Editor with The New Stack, covering DevOps and software development tools
The New Stack
Episode: Is No-Code Really Dead?
Rob Sanfilippo
Analyst at Directions with extensive experience at Microsoft
Directions on Microsoft
Episode: Is No-Code Really Dead?
David Berry
Newest Directions analyst specializing in SharePoint and Microsoft 365, with 25 years of experience as a solution architect.
Directions on Microsoft
Episode: Microsoft 365 Copilot Chat vs. OpenAI's ChatGPT: How to Choose

Host

Mary Jo Foley
Editor-in-Chief at Directions on Microsoft; long-timeMicrosoft coverage focusing on licensing, governance, and enterprise tech strategies.

Reviews

4.4 out of 5 stars from 18 ratings
  • Technical issues continue - episode restarts

    The technical issues continue. I would really like to listen to this but each one spontaneously restarts at various times. A little podcast export QC would go a long way. Otherwise great content and knowledgeable voices here.

    Apple Podcasts
    2
    Bsigrist
    United States2 years ago
  • Well worth a listen

    Learnt some very valuable information.

    Apple Podcasts
    5
    @Harish2000
    Australia3 years ago
  • Good Stuff

    Always find out something I didn't know. Podcasts on Fabric and ChatGTP are outstanding.

    Apple Podcasts
    5
    The Stoic's Porch
    United States3 years ago
  • Technical Issues?

    The podcast seems good and interesting, except the two episodes I’ve listed suddenly restart at the beginning at least once while playback continues.

    Apple Podcasts
    2
    Geoff 1212
    United States3 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Guests deliver expert, in-depth insights—great for listeners who work with Microsoft products.
Content is valuable and provides actionable information on licensing and enterprise tech.
Positive feedback on topics like AI, licensing, and governance, with occasional notes on production quality.
Technical issues continue - episode restarts and a few listeners report playback problems.

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Talking Points

Recent interactions between the hosts and their guests.

SQL Server Migrations: Tips to Help You Prepare
Q: Should enterprises consider buying Extended Security Updates?
They can be expensive, and often are a signal of poor planning. However, there may be scenarios where buying them makes sense if the migration is delayed.
SQL Server Migrations: Tips to Help You Prepare
Q: What should customers know about the differences between migration and upgrading?
Migration involves transferring the database without needing to rewrite applications, while upgrading means adopting a new version. The compatibility mode allows existing databases to behave like their previous versions.
Microsoft 365 Copilot Licensing: Five Things You Need to Know
Q: What tips do you have for negotiating with Microsoft about 365 Copilot?
Customers should leverage their E3 status and the prospect of moving to E5 to negotiate better deals, especially focusing on multiple purchases to increase leverage.
Microsoft 365 Copilot Licensing: Five Things You Need to Know
Q: What are the costs associated with Microsoft 365 Copilot licensing?
The costs include the monthly subscription fee of $30 per user, as well as potential additional fees related to E5 licenses and SharePoint Advanced Management.
Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
Q: Is it realistic to say, okay, customers, you can just simply abstain?
Customers may not have to be a frontier firm, but they need diligence to manage their needs against Microsoft's AI push.

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Frequently Asked Questions About This Podcast

What is This Podcast about and what kind of topics does it cover?

This show centers on Microsoft strategy, licensing, and enterprise-grade deployments, with a focus on practical governance, negotiation tactics, and transition plans for large organizations. Episodes frequently cover licensing shifts, Copilot and AI governance, and the evolving role of Exchange, with guests who bring deep Microsoft experience and licensing expertise. Listeners are likely IT leaders and practitioners navigating complex contracts, cloud-first transitions, and governance concerns, seeking actionable guidance rather than high-level theory. A standout feature is the consistency of licensing and negotiation insights from seasoned Directions analysts, offering listeners reliable, vendor-aware perspectives for enterprise decisions.... more

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this podcast launched 4 years ago and published 61 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on this podcast?

Recent guests on this podcast include:

1. Andrew Snodgrass
2. Jim Gaynor
3. Dean Bedwell
4. Tony Redmond
5. Rob Helm
6. Steve Kelley
7. Darryl Taft
8. Rob Sanfilippo

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