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
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.
Roadmap
Updated: March 20, 2026 · by Jim Gaynor
Skype for Business Server
ESUs for Skype for Business Server 2015 and 2019 end Apr. 14, 2026, leaving Skype for Business Server SE as...
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...
Infographic
March 17, 2026 · by Jim Gaynor
Server Application Version Support
Chart shows several server application versions and their eligibility for Microsoft product support on recent versions of Windows Server and...
Roadmap
March 16, 2026 · by Jim Gaynor
Microsoft 365 Backup
M365 Backup has added individual file/folder restores, multi-departmental billing, and GCC availability in Q1 2026.
Roadmap
Updated: March 12, 2026 · by Jim Gaynor
Server Application Version Support
Chart shows several server application versions and their eligibility for Microsoft product support on recent versions of Windows Server and...
Analyst Report
Updated: March 10, 2026 · by Jim Gaynor
Microsoft 365 Backup Targets Exchange and SharePoint Online Using a PAYG model
Microsoft 365 Backup improves policies and management but falls short of comprehensive M365 service backup.