Your agent will double-book you And call it done I run two calendars, one for ea
By John Aspinall ✱ · October 19, 2026 · Curated by George's Blog
Your agent will double-book you
And call it done
I run two calendars, one for each part of my work life.
If my booking agent could only see one of them, it would do exactly what I asked and still get it wrong.
It would find an open slot, book the meeting, and report the task as done.
Then I would find the clash when both meetings showed up.
So I gave it a simple rule.
Check the slot on both calendars before you create anything.
If there is an overlap, flag it to me. Do not book it. Do not pick a winner.
That one rule saves me from cleaning up after a booking that looked successful.
If you use an agent to book meetings, steal this setup today.
1. Connect every calendar you live on, not just your main work one.
2. Tell the agent, in plain words, to check every calendar before it books.
3. Tell it to flag an overlap and stop, not choose for you.
4. Test it with a fake clash. Put a hold on one calendar, ask for that same time, and see if it catches it.
Do the fake test before a real client does it for you.
If your agent books meetings for you, how many of your calendars can it actually see right now?