A scheduling assistant that handles the back-and-forth
An AI scheduling assistant checks your calendar, works out real availability, proposes times to the other person, and books the meeting once a slot is agreed. It takes over the five-message thread it usually takes to find a time for two or three people across two time zones.
It covers one-off requests (“find 30 minutes with Priya this week”) and recurring ones (“keep our Tuesday 1:1 on the calendar, and move it if either of us has a conflict”).
It also does the tedious parts: converting time zones, protecting your focus blocks, and following up when the other person goes silent.
What you hand off
A scheduling instruction typically covers:
- Checking your real availability, including buffer time and focus blocks you’ve set
- Proposing a short list of times to the other person, in their time zone
- Handling replies, counter-proposals and reschedules without you in the thread
- Booking the meeting and adding it to your calendar once a time is agreed
- Following up once or twice if someone stops replying, then flagging it back to you
- Keeping recurring meetings alive by rebooking around conflicts, holidays or cancellations
A booking, worked through
For example, Sam asks their operator: “Find 30 minutes this week for me and Priya at Brackenwold Studio to talk about the proposal. Propose three times and book it once she picks one.”
The operator checks Sam’s calendar for open slots this week, skips the focus block on Wednesday mornings, and drafts a message with three options across Tuesday and Thursday. Because it’s the first outreach to Priya, the message waits for Sam’s approval. Sam approves it at 9:02 a.m., and it goes out by email a minute later.
Priya replies at 11:15 a.m., picking Thursday at 2 p.m. and asking for 45 minutes. The operator checks that the extra 15 minutes doesn’t create a conflict and drafts a confirmation for Sam to approve. Sam approves from their phone. By 11:20, the meeting is on both calendars, and Sam’s task log records who was scheduled, what was proposed and what was confirmed.
Two days later, Priya’s assistant emails to push the call to Friday. The operator finds Friday open on Sam’s calendar, drafts the reschedule, and holds it for Sam’s approval, since it changes a commitment already booked. Sam approves in ten seconds, and the change is logged like the original booking.
What stays with you
Your operator checks availability and drafts proposed times on its own, since that changes nothing outside its workspace. Sending the first message and confirming a booking both wait for your approval by default, because each puts something on another person’s calendar in your name.
If you book the same kind of meeting often, like a weekly team sync, you can pre-approve that booking so it runs without a check-in. You can switch it back to “always ask” at any time, and the change applies from the next run.
Setting it up
- Connect your calendar and the channel used to reach other people (email, WhatsApp, or wherever you normally schedule).
- Give it the standing order: what kinds of meetings to schedule, your availability preferences, and any recurring bookings to maintain.
- Set your approval rules: what needs your OK before it’s sent, and which pre-approved meetings can run automatically.
- Tell it where to notify you: in the channel you used to ask, or in your regular brief.
One-off requests and recurring bookings run through the same operator and the same rules. When a recurring meeting stops making sense, such as for a project that has wrapped up, tell it to stop and it drops the standing booking.