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Onboarding Plan for Executive Assistant for Calendar Management

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Overview

This guide walks you through setting up your Executive Assistant for Calendar Management, starting with basic scheduling and building up to proactive calendar optimization. Total Setup Time: ~15-20 minutes (can be done in phases)

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Phase 1: The Fundamentals

Teach your EA the basics of managing your calendar

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1.1 Hire Your Executive Assistant

Start by hiring your worker with a clear role description. Hiring prompt:

“I want to hire an executive assistant to help me manage my calendar. They should focus on scheduling meetings, shaping my calendar and helping me prepare. I use Google Calendar. My timezone is [YOUR TIMEZONE].“

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1.2 Connect Tools

Go to your worker’s settings and connect:

• Google Calendar (or Outlook) — required for all calendar functions
• Notion (or Google Docs) — recommended for meeting prep and notes

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1.3 Teach the Worker Where Your Contacts Are

Your worker needs a way to find email addresses when scheduling meetings. Let’s check what’s available. Check prompt:

“What contacts do I have on my Gmail account?”

If your worker can list your contacts: You’re all set. Just add this instruction:

“Always search my Gmail contacts when you need someone’s email address.”

If your worker cannot access contacts: Check if your calendar has enough history:

“Check my calendar for meetings with colleagues in the last 2 weeks with the same company email. Identify who my colleagues are and what their emails are. Please add these contacts to your memory so you can use their emails to schedule meetings when I ask.”

If contacts are limited (or for personal contacts): You can directly teach your worker key contacts:

“Here are some important contacts to remember:

• [Name] — [email] (my manager)
• [Name] — [email] (my assistant)
• [Name] — [email] (my brother)
• [Name] — [email] (my accountant)”

This is especially useful for personal contacts that won’t appear in work systems.

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1.4 Teach Your Scheduling Preferences

Setup prompt:

“Here are my scheduling preferences:

• By default meetings should be 30 minutes
• By default add a Google Meet link for video calls
• If no email is provided, try to get it from Gmail contacts or recent meeting attendees. If unsure, ask.”

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Phase 2: Automate Your Daily Brief

Start each day knowing exactly what’s ahead

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2.1 Setup Daily Briefs

Have your EA send you a summary of your day every morning, so you always know what’s coming and what to prepare. Step 1 — Teach the process:

“When I ask you to help me do my ‘Daily Briefing’ I want you to check my calendar for the day. For each meeting confirm attendees, description, if there’s any meeting prep, context or actions required before. Then send me a summary through WhatsApp and a list of action items (if any).”

Step 2 — Schedule it:

“Every weekday at 8am I want you to execute my ‘Daily Briefing’”

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2.2 Improve Daily Briefs with Links to Pre-Read Materials

Now that you have scheduled daily briefs, make them richer by including relevant documents and context. Setup prompt:

“Enhance my scheduled daily briefings: For any meeting that mentions the topic in the title or description, check if we have any docs on Notion that are relevant pre-read and include the links. If it’s a 1:1 also include the last time we met.”

Or if you use Google Docs:

“Check my Google Docs for any existing notes or docs related to that person or project before the meeting.”

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Phase 3: Proactive Calendar Shaping

Let your EA prepare the week ahead and protect your time Instead of reacting to a packed calendar, have your EA proactively review and shape your week — blocking focus time, flagging conflicts, and making sure your schedule reflects your priorities.

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3.1 Share Your Calendar Preferences

First, teach your EA what an ideal week looks like for you. Setup prompt:

“Here are my calendar preferences:

• At least 3 focus time blocks per week, 3 hours each, ideally in mornings
• Avoid meetings before 9am (gym) and after 7pm (family dinner)
• Friday afternoons: avoid meetings
• Group back-to-back meetings for more uninterrupted focus time”

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3.2 Setup Weekly Calendar Review

Have your EA review your upcoming week every Friday and proactively fix issues before they become problems. Step 1 — Teach the process:

“When I ask you to do my ‘Weekly Calendar Review’, check my calendar for the following week, schedule focus time to protect it, and check if any preferences are broken. If yes, send an email and propose alternatives.”

Step 2 — Schedule it:

“Every Friday at 3pm run my ‘Weekly Calendar Review’”

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3.3 Protect Time for Your Priorities

Take calendar shaping further by connecting your priorities, so your EA blocks time for what matters most. Option A - If you use Notion for tasks:

“Update my Weekly Calendar Review to also check my priorities on the [PAGE NAME] page on Notion (tasks assigned to me with status ‘To Do’ or ‘In Progress’) and book slots for the top 3. Try to infer how long they will take and you can book on top of focus time. On each slot include the task in the title and details in the description.”

Option B - If you don’t have a to-do list:

“Every Monday morning, ask my top 3 priorities for the week via WhatsApp. Use these to block focus time slots during the week.”

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Phase 4: Delegate Meeting Scheduling

Let others book meetings directly through your EA

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4.1 Setup Booking Rules

Give your EA clear rules for handling meeting requests from different people. Setup prompt:

“Here are the rules you should follow when getting meeting requests with me:

• If it’s requested by me, when I add you to an email thread, always share availability
• If it’s requested by a colleague with the same business email domain as me, always share availability and accept suggestions and book directly while inviting them if they work
• If it’s [BOSS NAME], my boss, give availability even if I have to move gym or focus time
• If it’s a person I’ve already mentioned or in the contacts, also accept
• If it’s an external person we’ve never discussed, research the person based on the email and send me an email asking for confirmation and sharing your research before replying to the person
• If it’s clearly spam, because it’s a known spam domain or clearly bot, just ignore”

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4.2 Start Using It

Now you can simply CC your EA on an email thread, or have people email them directly to handle booking autonomously. Example uses:

• Forward a scheduling email to your EA: “Can you find a time for this?”
• CC your EA on a thread: “Adding my assistant to help find a time.”
• Share your EA’s email with trusted contacts for direct booking

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Quick Reference: What’s Needed Per Phase