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.

The first problem became immediately apparent: ChatGPT couldn’t actually access anyone’s calendar. It couldn’t see their free/busy information, couldn’t navigate to their calendars, and couldn’t check availability. All it could do was suggest times based on when I was free, which wasn’t particularly helpful since I already knew my own schedule.

This is a fundamental limitation that makes the assistant nearly useless for group scheduling. If I just needed to know when I’m free, I could check my own calendar. The whole point of using an AI assistant for scheduling is to coordinate across multiple people’s schedules—something ChatGPT simply couldn’t do.

The Gemini Experience

Since we’re all Google Workspace users, I thought Gemini would fare better. After all, it’s Google’s own AI assistant, and it should have better integration with Google Calendar and Workspace, right?

Wrong.

Gemini had the exact same limitations as ChatGPT. It couldn’t access calendars, couldn’t see free/busy information, and couldn’t coordinate schedules across multiple people. To make matters worse, it was also noticeably slower than ChatGPT, which meant that even if I wanted to use it for scheduling (which I didn’t, since it couldn’t actually do the job), I could manually schedule the meeting faster myself.

The Reality Check

This experience highlights a significant gap between what AI assistants are marketed as being able to do and what they can actually deliver in practice. Calendar management and meeting scheduling are frequently cited as use cases for AI assistants, but the reality is that they lack the necessary integrations and permissions to actually perform these tasks effectively.

For group scheduling to work, an AI assistant would need:

• Access to multiple people’s calendars
• The ability to read free/busy information
• Permission to view calendar details (at minimum, availability)
• The ability to actually create calendar events

None of the assistants I tried could do any of these things.

What This Means

I’m not writing this to bash AI assistants—they’re incredibly useful for many tasks. But this experience is a reminder that we need to be realistic about their current capabilities and limitations. Just because an AI assistant could theoretically help with a task doesn’t mean it can actually do it in practice.

For now, when it comes to scheduling meetings with multiple people, the old-fashioned approach—checking calendars manually or using dedicated scheduling tools—is still faster and more reliable than trying to use AI assistants that can’t actually access the information they need.

Maybe this will change in the future as integrations improve and permissions become more granular. But for now, AI assistants for meeting scheduling remain more promise than reality.