You know the routine. Your executive wants to connect with a few people outside the organization. You check the calendar, find some openings, and send an email offering three possible times.
One person responds the next day. Another replies on Friday. By Monday, two of the original options are gone, your executive has added a last-minute commitment, and someone else is traveling.
So you start again.
Scheduling is one of those responsibilities that can quietly consume a surprising amount of an EA's day. A meeting that should take 30 minutes can require several days of coordination, especially when you're dealing with multiple organizations, different time zones, and calendars you can't access.
A few of The Curve's readers brought up this challenge in our recent survey (We're still welcoming responses, so feel free to share your thoughts if you haven't already!). One mentioned that coordinating board meetings across external calendars can take weeks. Another wanted help finding available meeting times among outside partners.
So we thought this deserved its own edition!
There are already plenty of scheduling tools available, and we use them every day. But even with Calendly, Outlook, Google Calendar, or Microsoft Bookings, there's still work involved in reviewing responses, comparing options, and figuring out what to propose next. This is one area where AI can be useful, even without direct access to your calendar.
AT A GLANCE
AI Level: Intermediate
Reading Time: 7 minutes
This Week: Using AI to compare availability, account for scheduling constraints, and reduce the back-and-forth of coordinating meetings.
You'll Learn: A practical scheduling workflow with prompts you can adapt to ChatGPT, Claude, Gemini, or your organization's approved AI tool.
Term of the Week: Constraint-Based Scheduling
A constraint is a condition that needs to be considered before making a decision. When you're scheduling for an executive, you probably work with constraints all the time without calling them that.
Your executive may prefer external meetings in the afternoon, need 30 minutes between appointments, or avoid calls immediately before a flight. A meeting might require a full hour, while the calendar only shows a 30-minute opening. An attendee might be available on Tuesday, but only in Pacific Time.
Constraint-based scheduling means looking at those requirements together to determine which options are actually workable. AI can help compare the information and identify overlapping availability. You still need to check the calendar before sending or confirming anything, particularly when availability changes throughout the day.
Here's how to put that into practice.
1. Give AI the Scheduling Information
Imagine you're coordinating a one-hour meeting between your executive and two external partners. You've already received their availability by email, and you've checked your executive's calendar. Here's what you have:
Participant | Monday, Oct. 26 | Wednesday, Oct. 28 |
Your executive | 10 AM–12 PM ET | 1–4 PM ET |
Partner A | 11 AM–2 PM ET | 2–5 PM ET |
Partner B | 8–10 AM PT | 11 AM–1 PM PT |
Your executive also needs a 15-minute buffer before the meeting and prefers to finish meetings by 3:30 PM ET. You could compare these manually, and for three people, it wouldn't take terribly long. But when the meeting involves six people, several time zones, or multiple rounds of changes, having AI organize the information becomes much more useful.
TRY THIS PROMPT: Copy the prompt below and replace the bracketed details with your own information. Add or remove participants as needed.
I'm an executive assistant coordinating a meeting involving multiple participants.
Meeting details:
1. Meeting duration: [30 minutes / 60 minutes / other]
2. Preferred date or date range: [Insert dates]
3. Time zone for the final schedule: [ET / CT / PT / other]
Participant availability:
1. Executive: [Insert available dates, times, and time zone]
2. Participant 2: [Insert available dates, times, and time zone]
3. Participant 3: [Insert available dates, times, and time zone]
4. Additional participants: [Add as needed]
Scheduling requirements:
1. Required buffer time: [Insert amount, if applicable]
2. Preferred meeting hours: [Insert preferences]
3. Existing restrictions or conflicts: [Insert details]
4. Other considerations: [Travel, meeting format, location, etc.]
Please compare everyone's availability and identify the meeting windows that meet all the requirements.
Convert all times to [preferred time zone], accounting for the specific dates and daylight saving time where applicable.
Present the results in a simple table showing the date, start time, end time, and any considerations.
Do not assume additional availability or change the meeting duration. If no suitable times exist, explain which requirements are preventing a match. Ask for clarification if important information is missing.
What You Should Get
For the example above, after converting Partner B's availability to Eastern Time, the overlapping meeting options are:
Monday, October 26: 11 AM–12 PM ET
Wednesday, October 28: 2–3 PM ET
Both options meet the required meeting duration and could accommodate the 15-minute buffer, provided those buffer periods are also free on your executive's calendar.
Now you have two specific options to verify and propose.
One detail worth remembering: AI sometimes makes mistakes when converting time zones, particularly around daylight saving time changes. Include actual dates whenever possible and double-check the conversion before sending anything.
2. Let AI Help With the Scheduling Email
Once you've verified the available times, you can use AI to prepare the email. You may already have a standard scheduling template, which is fine. AI becomes more helpful when you need to adjust that template for a particular situation, especially if you're coordinating several meetings at once.
TRY THIS PROMPT:
I'm an executive assistant scheduling a meeting on behalf of [Executive's name and title].
Meeting details:
1. Recipient(s): [Name(s) or relationship to executive]
2. Purpose of meeting: [Brief description]
3. Meeting format: [Phone / Zoom / Teams / In person]
4. Meeting duration: [Insert duration]
5. Available dates and times: [Insert verified options with time zones]
Communication preferences:
1. Tone: Warm, professional, and natural
2. Length: Short and easy to read
3. Additional context: [Previous conversation, rescheduling, travel considerations, etc.]
Draft an email offering the available meeting times and asking the recipient to confirm their preference.
Make the next step clear. Do not imply the meeting is confirmed until all parties have agreed.
Avoid overly formal language, unnecessary explanations, and details I haven't provided.You can review the draft, make any adjustments, and send it.
3. When Someone Changes Their Availability
Now suppose you've sent the options, but the replies don't line up.
One participant is no longer available on Monday. Another prefers Wednesday but can't start until later in the afternoon. Meanwhile, your executive still needs a full hour and has another commitment immediately afterward.
Instead of comparing everything again, return to the same AI conversation and provide the changes.
TRY THIS PROMPT:
I'm coordinating a meeting and need to reassess the available times based on new information.
Original meeting details:
1. Meeting duration: [Insert duration]
2. Previously proposed dates and times: [Insert options]
3. Original scheduling requirements: [Insert constraints or refer to the details earlier in this conversation]
New information:
1. Participant 1: [Updated availability or restrictions]
2. Participant 2: [Updated availability or restrictions]
3. Executive: [New commitments or changes, if any]
4. Other updates: [Insert details]
Please compare the updated availability and determine whether any of the original options still work.
If none work, identify the scheduling conflicts and suggest what additional availability or clarification I should request.
Present the findings in a short table and recommend the next scheduling step.
Do not shorten the meeting, move existing commitments, or assume anyone is flexible without confirmation.For more complicated scheduling, you can also ask AI to maintain a simple table showing each participant's latest availability, outstanding questions, and which options have already been ruled out. Just make sure you're working with current information. AI doesn't automatically know that someone accepted another meeting five minutes ago.
4. Can AI Check Calendars and Book Meetings for You?
This is where the tools you're using matter.
If you use ChatGPT, Claude, or Gemini without a calendar connection, you can still provide scheduling information and ask the tool to compare it. But it won't know what's currently on your executive's calendar unless you supply that information.
If your organization uses a supported calendar integration, some AI tools may be able to retrieve calendar information or assist with scheduling tasks. The available features depend on the product, account settings, and permissions.
And if you're using Calendly or Microsoft Bookings, those platforms can already handle much of the appointment-selection process.
For EAs coordinating external meetings, however, there's a common limitation: you usually don't have access to everyone else's calendar. A booking link can show your executive's availability, but it doesn't automatically solve conflicts among several external attendees. That's why the workflow we covered today can still be useful. You can gather the information from emails or scheduling responses, ask AI to compare it, and then use your existing calendar tools to confirm the appointment.
You don't need to introduce another application to make the process easier.
A Few Things to Check Before You Use This Workflow
Be careful with calendar information. Executive calendars can contain confidential client names, business plans, private appointments, and other sensitive details. Follow your organization's AI policies, use approved tools, and avoid sharing information that isn't necessary for the task. For practice, fictional names and sample availability work just as well.
Check the actual calendar. An AI-generated list of available times is only as accurate as the information you provided. Before sending options, verify that the slots are still open and that any required buffers are available.
Pay attention to meeting duration. A 30-minute opening isn't sufficient for a one-hour meeting. AI may occasionally suggest an option that looks close enough but doesn't meet every requirement. Ask it to explain its reasoning, then check the result yourself.
Keep your executive's preferences in mind. Some scheduling decisions involve judgment that isn't captured in a calendar. You know which meetings need extra preparation, which relationships require flexibility, and when your executive needs time between commitments.
AI UPDATES OF THE WEEK
OpenAI announced ChatGPT Slides, which allows eligible users to create, edit, and collaborate on presentations, including charts, images, and text. Presentations can be exported to PowerPoint, PDF, or Google Slides.
OpenAI introduced locked chats, allowing users to protect selected conversations with a PIN or supported device authentication. Locked chats are hidden from regular chat history and search, although organizational retention and compliance policies still apply.
Google introduced a dedicated Gemini business hub with tools for creating branded content, analyzing finances, and understanding customer insights. The update is designed primarily for small-business owners.
We’d still love to hear from you!
If you haven’t taken our 2-minute survey yet, there’s still time. Tell us how you’re using AI, where it’s falling short, and what you want to learn next. Your responses help us understand what EAs actually need from AI.
SEE YOU NEXT WEEK!
And please keep sharing what you’re learning with us. Your real answers help us make each issue more useful to the EAs reading it.
The Base Team
