Jim leads the Directions on Microsoft editorial team and has been writing about technology since the early 1990s. Most recently he's covered Teams, Windows Server and related OSs, and enterprise IT infrastructure.
He brings with him over 15 years supporting and teaching academic and researching technology at large universities like University of Washington and The Ohio State University, a decade in operations management for a global engineering firm, and experience as technical producer of a live service game based on the popular Magic: The Gathering property.
Jim holds a B.A. with graduate studies in philosophy and a minor in computer science from The Ohio State University.
Latest Content by Jim Gaynor
Analyst Report
Updated: May 11, 2026 · by Jim Gaynor
Need to Know: Terms and Concepts for Understanding Microsoft VDI
This report clarifies evolving Microsoft VDI terminology, emphasizing AVD, Windows 365, host types, and deployment concepts.
Roadmap
Updated: April 29, 2026 · by Multiple Authors
Business Applications Roadmap
The Business Applications Roadmap describes Microsoft products (on-premises software and cloud services) that provide traditional business functionality like collaboration, email,...
Roadmap
Updated: April 17, 2026 · by Jim Gaynor
Azure VMware Solution Roadmap
The VMWare Rapid Migration has been reworked to one-time credits, with a new deadline of Jun. 30, 2026.
Roadmap
Updated: April 15, 2026 · by Jim Gaynor
Skype for Business Server
Newly-announced Period 2 ESUs support Skype for Business Server 2015/2019 through Oct. 2026.
Analyst Report
Updated: April 2, 2026 · by Jim Gaynor
Teams Premium Goes Beyond Meetings and Webinars
Teams Premium features focus mainly on Teams events and AI features that overlap with Microsoft 365 Copilot, but Premium’s data...
Roadmap
Updated: April 1, 2026 · by Jim Gaynor
Teams Meetings and Events
Teams live events will retire on June 30, 2026, and webinar and town hall advanced features are now part of...
Roadmap
Updated: March 31, 2026 · by Jim Gaynor
Teams Phone
Updates include extensibility for contact center solutions and a Phone Attendant Agent planned for mid-2026.
Roadmap
Updated: March 25, 2026 · by Jim Gaynor
Teams Premium
Teams Premium focuses on meeting security and intelligent recap after advanced event features move to Teams Enterprise.
Roadmap
Updated: March 20, 2026 · by Jim Gaynor
Planner Roadmap
A major Planner update in early 2026 brings an AI assistant to all users and breaking changes to some features.
Analyst Report
March 17, 2026 · by Jim Gaynor
Teams Enterprise Gains Events and Places from Premium
Some features of Teams Premium are moving to Teams Enterprise at no additional cost, including advanced webinars and town halls...