My AI scheduling bot double booked me 4 times in one day last Tuesday

I set up this smart calendar assistant to auto-schedule my client meetings. It was supposed to learn my patterns and avoid conflicts. Instead it put a 10 AM and a 10:15 AM at different locations across town. I showed up late to both and had two angry clients. When I checked the logs the AI had a conflict resolution bug where it ignored time overlap. I ended up uninstalling the whole thing and going back to a paper planner for now. Has anyone else had an AI tool make your life harder instead of easier?

3 comments

3 Comments

graydavis15d ago

I use a tool called Reclaim.ai that has a "buffer time" setting I had to manually turn on. It puts 15 minute gaps between meetings and checks for travel time if you link your maps. Took me a full week of tweaking the settings before it stopped double booking me. The default config on most of these scheduling bots is TERRIBLE, you have to babysit them at first like a toddler.

the_elliot15d ago

God yeah, the babysitting part is too real. I spent 3 days fighting with one bot that kept scheduling meetings at 7 AM because it thought my "available hours" checkbox meant something different than what it actually was. You basically have to manually approve everything for the first month or it will book you into a nightmare. The worst part is when it syncs your calendar and just starts grabbing old blocked time as free slots. I had to completely delete and reinstall one app twice before it finally stopped doing that.

the_alice15d ago

The calendar syncing issue is exactly what drove me crazy too. I started just blocking off chunks of time as "Busy - Do Not Move" on my calendar before syncing anything, which forced the bots to leave those alone. It took a few tries but once I got the hang of labeling stuff specifically for the bot to see, it finally stopped grabbing my old dentist appointments as open time.