The executive assistant workflow for offering meeting times

"Send them some times for next week" is the most common sentence in an executive assistant's day, and it hides real work: check the exec's calendar, maybe intersect it with another leader's, respect the no-meetings-before-10 rule, convert for the other side's timezone, and type it all up — accurately, because errors here are visible ones.

Encoding the rules once

OpenSlot lets the rules live in the controls instead of your head: working hours (start the day at 10:00 if that's the standing rule), weekends off, tentative counts as busy, shortest slot 30 or 60 minutes. Set once; every list you generate respects them.

The twenty-second version of the task

Add the exec's calendar (and the other principal's, if it's a joint meeting — the list only shows times when everyone is free), pick the counterparty's timezone, choose the window, generate:

All times in US/Eastern
• Today 07/08
  03:30 PM - 04:00 PM
  05:00 PM - 05:30 PM
• Thursday 07/09
  09:30 AM - 10:30 AM
  12:00 PM - 01:00 PM
  02:30 PM - 03:00 PM

Copy into the email, or use the Outlook add-in to insert it directly into the message you're already composing. Because it reads free/busy live, a hold that landed on the calendar ten minutes ago is already reflected — no more offering a slot that quietly disappeared this morning.

The rules worth encoding first

Four settings carry almost all the value, and they are the four that usually live in an assistant's head. Working hours, so the day starts when the principal actually takes meetings rather than when the calendar grid starts. Weekends off. Tentative counting as busy, so a provisional hold cannot be offered out from under someone. And a minimum slot length that matches the meeting being booked.

That last one has a wrinkle worth knowing, because it explains a question you will otherwise ask yourself: a slot has to end inside working hours, not just start inside them. With a 10:00–18:00 day and a 60-minute minimum, 17:30 is not offered, because the meeting would overrun. If a gap you can see on the calendar is missing from the list, this is almost always why.

Joint meetings and the other principal

The moment two executives need to be in the same room, hand-reading two grids stops scaling — and it is exactly the case where a mistake is most visible. Adding both calendars returns only the intersection: times when every person selected is free simultaneously. On Pro that extends to 40 calendars at once, which covers a full leadership team or an interview panel without breaking the task into pieces.

The same intersection is what makes a sixty-day window useful rather than theoretical. "Find me ninety minutes with all four of them before the end of the quarter" is a question nobody wants to answer by scrolling, and it is the same single click as next Tuesday.

The failure this actually removes

The expensive error in this job is not typing a wrong time. It is offering a slot that was true when you looked and false when they replied — the hold that landed while you were drafting, the meeting the principal accepted from their phone between your check and your send. A list built from live free/busy at the moment you generate it closes most of that window, and generating a fresh one takes long enough to be worth doing again if the draft has been sitting open.

One prerequisite is worth checking early: you need to be able to read the calendars involved. Inside one Microsoft 365 organization that is usually true by default. For a principal in a different tenant — a board member, an advisor — it is not, and no tool can work around it. That case is covered in scheduling with people outside your company.

Common questions