My agent books meetings for me. It checks two calendars first. I run two jobs, s
By Jaspinall · October 29, 2026 · Curated by George's Blog
My agent books meetings for me.
It checks two calendars first.
I run two jobs, so I have two calendars. My agent can see both, and before it puts anything on either one it has two rules:
1. Check that time slot on both calendars.
2. If anything overlaps, tell me before it creates the event.
Without those rules, an agent does what a new assistant does on day one. It finds an open slot on the calendar it was given, books it, and sends the invite. The conflict on the other calendar shows up when two people are waiting for you at 2pm.
The agent didn't screw up there. It only knew about one calendar.
Most AI scheduling breaks the same way. People connect the one account the tool supports and assume it sees their whole week. It sees what you connected and nothing else.
So before you let an agent book anything:
→ Connect every calendar you actually live on, work and personal
→ Write the conflict check into its instructions, not just your head
→ Make it flag the overlap instead of picking a winner
That last one matters most. The agent doesn't know your investor call beats the dentist. You do.
Open your agent's instructions today and count how many calendars it can see.