Scheduling rules to agree first
An assistant can only defend your time if they know what you're defending. Before handing over the calendar, write down:
- Meeting hours. The window when external meetings may be booked, and days you keep meeting-free.
- Default lengths. For example 25 or 50 minutes, so there is always a short gap before the next call.
- Buffers. Time before big meetings for prep, after travel, and around lunch.
- Focus blocks. Recurring blocks that only you can release.
- Daily cap. A maximum number of meetings per day, after which requests move to the next open day.
- Who jumps the queue. People whose requests can override the rules, and how far.
Handling meeting requests
When a request arrives, the assistant checks it against your rules, offers two or three times (in the other person's time zone), sends the invite with a video link or location, and adds an agenda or the reason for the meeting to the event description. Requests that don't fit the rules come to you with a recommendation, not a question.
Scheduling links help for high-volume external booking, but many executives prefer that the assistant handles investor, board and senior customer meetings personally. It reads better and avoids awkward double bookings.
Agendas and prep notes
For each important meeting, the assistant can attach the last email thread, relevant documents, a short note on who's attending and what was agreed last time. You open the event and everything you need is there.
Time zones and travel
Calendars go wrong most often around travel. Ask the assistant to set the event time zone explicitly for each meeting, show a second time zone on your calendar when you're away, block travel time as busy, and add flights and hotel details as events with confirmation numbers in the notes.
Permission levels
Google Calendar and Outlook let you share a calendar at different levels, from seeing free and busy time to making changes. An assistant who schedules for you needs to be able to make changes; they rarely need to manage sharing settings. If you keep personal events on the same calendar, mark them private so the assistant sees that you're busy without seeing details, or keep a separate personal calendar that you share only as free and busy.
The weekly preview
At the end of each week, a short preview of the next one: key meetings, travel, deadlines, gaps that need decisions and anything that clashes with your rules. Most clashes are easier to fix on Friday than Monday morning.
Questions to ask
Should the assistant accept invites on my behalf?
For routine internal meetings that fit your rules, often yes. For anything external or senior, the assistant should check first or follow a specific rule you've agreed.
What about recurring meetings I've outgrown?
A quarterly review of recurring meetings is a good standing task. The assistant lists each one with attendance and purpose, and you decide what to cut or shorten.
Can one assistant manage calendars for several executives?
It can work for a small leadership team with shared rules, but agree who wins when two executives want the same slot with the same person.
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