The Directions on Microsoft Briefing Podcast Microsoft Ignoring Your Org's Needs? We Have Some Tips for That
Jan 23, 2026
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.
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AI Focus Is Squeezing Core Products
- Microsoft's intense focus on AI is diverting attention from stable, critical products customers rely on.
- This shift causes benign neglect and consolidation of long-running enterprise technologies like Windows Server and Intune.
The Distracted-Girlfriend Meme Analogy
- Jim compares Microsoft's behavior to the meme of a man turning to stare at another woman while ignoring his girlfriend.
- He uses this to illustrate Microsoft ignoring existing products while fixating on AI.
AI Demands Big Capital And Product Pruning
- AI requires massive capital spending on data centers and GPUs which locks in long-term costs.
- Microsoft is cutting operational expenses and pruning products to offset those capital investments.