Jim Gaynor
Leads the Directions on Microsoft editorial team and is an analyst focused on Microsoft enterprise technologies, with extensive experience covering Teams, Windows Server, and enterprise IT infrastructure since the early 1990s.
Best podcasts with Jim Gaynor
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Jan 23, 2026 • 24min
Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
Jim Gaynor, who leads the Directions on Microsoft editorial team and analyzes Microsoft enterprise tech, talks about Microsoft’s intense AI push and how it crowds out other products. He names Windows Server, Intune and management tools as areas feeling neglected. He outlines negotiation tactics, when to wait on AI, and how competition from Apple and Google can help.
