1. Name the calendars that count
Ask for calendars grouped by connected account, then select the work and personal calendars you want included. Do not assume every calendar on a device is available through the connected provider.
Example requestUsing Pear, list the calendars I can read, grouped by account. Ask me which work and personal calendars to include. Confirm my planning timezone. Do not copy, create or change any events.
What to check
Compare the list with Outlook and Apple Calendar. A locally stored calendar or an unconnected account will not become available just because it appears on your phone.
2. Compare a small, explicit time window
Request suggestions based on the selected calendars only. Include travel buffers and working-hour preferences rather than expecting the assistant to know them.
Example requestRead my selected work and personal calendars for the next five weekdays in Australia/Sydney. Suggest three 45-minute slots between 9am and 5pm, leaving 30 minutes either side of existing events. Show the date and timezone, identify any conflicts, and say which calendars you could not read. Keep personal event titles out of the work-facing summary. Do not create an event.
What to check
Check each proposed slot in both source calendars. Confirm recurring and all-day events, timezone conversions and travel time. Availability is a snapshot; another event can be added before you book.
3. Choose one destination before booking
If you decide to create an event, choose one writable calendar. Recheck the slot and review the exact event before approval. Personal context need not be copied into a work event.
Example requestRecheck the slot I selected against both calendars. If it is still suitable, prepare one event on the destination calendar I name. Show the account, calendar, title, start, end, timezone and any attendees for review through the applicable approval flow. Do not create a second copy or include private event details.
What to check
After execution succeeds, open the destination calendar and check the event’s time, timezone and attendees. Confirm there is only one event. If your client cannot write, use the reviewed suggestion to create it yourself.
If the result is not what you expected
Only one account appears
Multiple connected accounts require Pear Pro. Confirm both accounts are connected in Pear and that each has calendar access. A second AI chat does not connect a second provider account.
The assistant suggests a busy slot
Check the exact calendars, date bounds, recurrence and timezone. Ask it to read the source events around that slot again. Treat free-time suggestions as a plan to verify, not a guaranteed reservation.
You want calendars kept in sync
Reading two calendars together does not set up a two-way sync. This workflow compares them on request and creates only the event you approve. Ongoing synchronisation requires a separate solution.
Know what you are connecting
This is an illustrative planning workflow. Pear permissions, provider access and the AI client’s plan govern available actions. ChatGPT Pro’s MCP path is read/fetch-only; writes require an eligible Business, Enterprise or Edu workspace. Follow your organisation’s policy before connecting a work account.
Read how Pear handles your data