15d • General discussion 💬
Calendar integration almost killed our product launch
Three weeks before launch, we're demoing our voice AI to a dental clinic. Perfect demo. AI sounds natural, understands everything, books the appointment.
Dentist watches, nods along. Then says: "So your receptionist still has to put this in Google Calendar?"
Me: "Uh, yeah, for now."
Dentist: "Then what's the point? You've just added a step."
Ouch. But he was right.
We had built this amazing conversational AI that could understand context, handle interruptions, sound completely human. But it couldn't actually DO anything. The receptionist still had to manually enter every appointment.
Spent the next month fixing it. Turns out calendar integration is way harder than I thought.
The problems nobody warns you about,
Timezones are evil
User in California says "book me for 3 PM." Our server in Virginia creates appointment at 3 PM Eastern. User shows up at 3 PM Pacific, appointment was 3 hours ago.
Now we explicitly confirm: "Just to confirm, that's Tuesday at 3 PM Pacific time, correct?"
Double booking race conditions
Two people call at the same time, both get offered 2 PM, both say yes. Now you have two people scheduled for the same slot.
Had to build a slot holding system. When AI offers you a time, it holds it for 5 minutes. Nobody else sees it as available during that window.
The "next Tuesday" problem
There are 52 Tuesdays in a year. Which one did you mean?
Started always including the full date: "Tuesday, February 4th" so there's no confusion.
What actually works now
We support Google Calendar, Outlook, and Calendly. Each has different APIs and different quirks but we built an abstraction layer so the AI doesn't care which one you use.
The flow:
- User asks to book
- AI checks actual availability in real-time
- Offers specific times
- Holds the slot
- Gets confirmation
- Creates the event with all details
- Sends invites to everyone
Whole thing takes about 45 seconds.
Real results
That same dental clinic is now a paying customer. Their receptionist went from handling 50+ booking calls a day to maybe 10. The AI handles the rest.
Best part? They can take bookings at 11 PM when someone remembers they need a cleaning. Receptionist isn't there but the AI is.
Their no-show rate dropped from 28% to 11% because the AI sends automatic reminders (24 hours before, 4 hours before, 30 minutes before).
The code part (briefly)
Google Calendar API isn't that bad once you get OAuth working. The tricky parts:
- Checking availability across date ranges
- Finding gaps in busy schedules
- Handling timezone conversions properly
- Creating events with all the metadata
Outlook/Microsoft Graph is more powerful but also more complex. Calendly is easiest but less flexible.
We ended up building connectors for all three because different businesses use different systems.
Lesson learned
You can have the smartest AI in the world but if it can't actually complete the task, it's just an expensive chatbot.
Calendar integration turned our product from "cool demo" to "this actually saves us money."
The dentist was right. If you're just moving work from the phone to the keyboard, you haven't really automated anything.
Anyone else struggled with calendar APIs? Google's timezone handling still gives me nightmares sometimes.
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Calendar integration almost killed our product launch
skool.com/brendan
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