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
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.
Analyst Report
Updated: February 18, 2026 · by Jim Gaynor
VMware Rapid Migration Plan Loses Incentives: Some Benefits for Commitment Remain
A Microsoft promotion offers benefits for customers who migrate VMware workloads to Azure VMware Solution.
Video
Updated: January 27, 2026 · by Multiple Authors
Directions Podcast. Season 5. Episode 2. Microsoft Ignoring Your Needs? We Have Some Tips for That
Microsoft's one-pointed AI focus may be clouding what your company really wants and needs. Directions analyst Jim Gaynor shares with...
Blog
January 16, 2026 · by Jim Gaynor
Does Microsoft care about what you care about?
Microsoft’s current obsessions might not include things your business needs. So, what can you do about it?
Roadmap
Updated: January 5, 2026 · by Jim Gaynor
Azure Virtual Machines Roadmap
Roadmap for Azure Virtual Machines.
Kits & Collections
Updated: November 13, 2025 · by Jim Gaynor
Microsoft Teams
This collection of Directions reports and resources can help organizations better understand the latest changes and roadmap for Teams, Microsoft's...