Google-Workspace

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When AI Assistants Fail: The Meeting Scheduling Reality Check
Process-MethodologyIndustry-Insights
Jan 11, 2026
3 minutes

When AI Assistants Fail: The Meeting Scheduling Reality Check

I recently tried to use AI assistants to solve what should be a straightforward problem: scheduling a meeting with three other people at my office. We’re all Google Workspace users, so I figured this would be a perfect use case for AI—especially given all the hype about AI assistants being able to handle calendar management and scheduling.

Spoiler alert: both ChatGPT and Gemini failed spectacularly.

The ChatGPT Experience

I started with ChatGPT, thinking it would be able to help coordinate schedules. My request was simple: find a time that works for me and three colleagues for a meeting.