Webinars

Every month, Directions Analysts & Experts convene live to discuss and answer questions on critical topics for Microsoft customers. Treat each webinar like a mini-training on Microsoft technologies, roadmaps, and licensing policies important to most enterprise-size organizations. Webinars are typically presentations followed by a live, interactive Q&A. Following the webinar, recordings are always available with navigation tools to jump straight to the slides you need.

Upcoming

Microsoft 365 for Government – What is it?

Microsoft 365 Government offers compliance with U.S. government regulations, but the higher the tier, the more features are missing. This makes understanding the value you’re receiving more complicated than for commercial customers.

This webinar covers the three tiers of Microsoft 365 for U.S. Government customers, and the feature limitations of the suite for government customers.

Webinar Slides

May 22, 2025 10:00 am – 11:00 am PT Request Access
Microsoft’s AI-Native Applications Strategy

Microsoft thinks that everything we know about application architecture will change as AI permeates every layer of the stack. And they’re putting their money where their mouth is with investments in new tools for what we’re calling “AI-native apps:” RAG, agents, fine-tuning.

What do you have to do to get ready? What does it mean for your data, for your developers, for managing your IT ecosystem? That’s what Barry Briggs will chat about – live, not a chatbot! – in our webinar.

June 19, 2025 10:00 am – 11:00 am PT Request Access

Past Webinars

Power Platform Overview

Rob Sanfilippo discusses the pieces of Power Platform including Power Apps, Power Automate, Dataverse, and Copilot Studio, including technical and licensing aspects.

April 17, 2025
Meteor 2025: Exchange & Skype for Business Server

All versions of Exchange Server and Skype for Business leave support in Oct. 2025, and Microsoft’s plans for “subscription editions” leave a small window for customers to upgrade and stay supported. Will you be ready? Rob Helm and Jim Gaynor explain Microsoft’s plans, discuss your options, and take your questions.

March 20, 2025 Available to All
What’s the Difference between Windows Server and Azure Local?

In this Webinar, Jim Gaynor & Greg DeMichillie discuss the latest versions of Microsoft’s on-premises server operating systems, Windows Server 2025 and Azure Local (formerly Azure Stack HCI), and the directions in which Microsoft is taking them.

February 20, 2025
Meteor 2025: The Next Wave of Windows and Office Migrations

A “mass extinction” of client software and services leaving support in 2025-2026 will trigger many migrations to new Windows and Office versions. Michael Cherry and Rob Helm explain and take questions on migration and deployment options.

January 23, 2025
Microsoft Roadmap Update, Dec. 2024

The Directions on Microsoft analysts assess recent changes and key trends in Microsoft’s enterprise technology roadmap. We look back at the most impactful announcements of 2024 and make predictions about what will matter in 2025.

December 5, 2024
GitHub Roadmap and Licensing

Rob Sanfilippo updates you on the latest GitHub innovations and licensing details.

November 21, 2024
Demystifying Microsoft Copilots

Wes Miller and Rob Sanfilippo distill the key Copilot offerings Directions has identified and highlight key features offered by each of them.

October 24, 2024
Rethinking and Optimizing the Windows Client OS

Windows 10 leaves support in Oct. 2025. Now is a good time to evaluate and optimize deployment of the Windows client OS for your organization. In this Webinar, Directions analyst Michael Cherry helps you rethink the role of the Windows client and address important questions.

September 26, 2024
Applying On-premises Licenses to Cloud Workloads

Rob Horwitz reviews your options to apply your Windows Server and SQL Server core licenses, and Windows Enterprise and Office suite user/device licenses, to service provider-hosted workloads.

August 22, 2024
Microsoft’s Ever-Expanding Compliance Landscape

Barry Briggs, former CTO of Microsoft’s own IT unit, discusses the continuing evolution of Microsoft’s compliance strategy and its technologies, now under the umbrella brand of Purview. Barry describes new features and capabilities in Purview, the licensing implications, and what still missing from Microsoft’s compliance portfolio.

July 25, 2024
Copilots

Rob Sanfilippo surveys Microsoft’s Copilot offerings, discussing their capabilities and differences. The services and tools for extending Microsoft’s Copilots and creating custom copilots are also covered.

June 27, 2024
Don't Look Up: Second Licensing Meteor Approaching

Joshua Trupin looks at the licensing changes Microsoft is making now that will fundamentally transform IT budgets yet again.

May 30, 2024