If you’re an EA, you know the drill — flipping between tabs, counting time zones on your fingers, placing holds that you’ll forget to delete, and fielding “can you move my 2pm?” messages while you’re already deep in a scheduling chain for someone else.

Chat with Cal is Carly’s free chatbot interface, and it’s built for exactly this. Instead of clicking through a calendar UI, you just type what you need in plain English. Think of it as texting a second EA who never sleeps and has instant access to every calendar you manage.

Here’s how to use it for the things you do fifty times a day.

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Move Meetings

Someone asks you to shift a meeting. Instead of opening the calendar, finding the event, dragging it, checking for conflicts, and sending updates — just tell Carly.

If there’s a conflict, she’ll tell you before doing anything.

More examples:

• “Push the board prep meeting to Friday at 10am”
• “Move tomorrow’s 1:1 with James to next Monday, same time”
• “Reschedule the investor call from Wednesday to Thursday afternoon”

You can also ask Carly to suggest a new time if you’re not sure when to move it:

Michael’s 2pm conflicted. When’s the next open 30-minute slot this week?

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Check Your Executive’s Schedule

The most basic thing — and the one you probably do the most. Just ask.

You type:

What’s on Michael’s calendar tomorrow?

Carly responds with a rundown of every event: times, titles, attendees, and locations. No opening a separate tab, no scrolling through a packed day view.

You can get as specific or broad as you want:

• “What does Michael have on Thursday afternoon?”
• “Is Michael free at 3pm on March 5?”
• “Show me Michael’s full schedule for next week”
• “Does Michael have anything with the marketing team this week?”

If you manage multiple executives, just specify whose calendar you’re asking about. Carly keeps them all straight.

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Place Holds

EAs live and die by holds. When your exec says “block something for me next Tuesday afternoon” or a recruiter asks you to tentatively reserve a panel interview slot — you need holds up fast.

One message, one hold.

Need multiple holds for the same thing (because you’re waiting on someone to pick a time)? Stack them:

Put holds on Michael’s calendar for:

• Monday 10am-11am
• Tuesday 2pm-3pm
• Wednesday 11am-12pm Title them all “Client call — hold”

When the time is confirmed, just tell Carly to remove the ones you don’t need:

Delete the Monday and Wednesday holds for the client call

No hunting through the calendar to find and delete each one individually.

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Create Events

You get an email: “Can you set up a 45-minute strategy session with the product team next week?” Instead of navigating to the calendar, clicking the right day, filling in fields — you type one message.

Carly creates the event with the title, duration, video link, and invites. She sends the calendar invitations automatically.

You can include as much or as little detail as you want:

• “Add a lunch block from 12-1pm every day this week”
• “Create an event called ‘Board Meeting’ on March 15, 9am-12pm, at 500 Howard St, San Francisco”
• “Schedule a 30-minute debrief right after Michael’s 3pm meeting tomorrow”

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Paste in Times and Let Carly Cross-Reference

This is where Chat with Cal saves the most time. You get an email from someone in another time zone with a list of times they’re available. Normally, you’d convert each one, then check each converted time against the calendar. That’s 10 minutes of tab-switching and mental math.

With Carly, you just paste the whole thing.

You type:

The client sent these times (they’re in Pacific):

• Monday 10am-11am
• Tuesday 9am-10am
• Tuesday 2pm-3pm
• Wednesday 10am-11am
• Thursday 1pm-2pm

Which of these work on Michael’s calendar?

Carly converts every slot to Eastern, checks each one against Michael’s calendar, and cuts straight to the answer:

Three options work:

• Monday 1pm-2pm ET
• Wednesday 1pm-2pm ET
• Thursday 4pm-5pm ET

Tuesday’s don’t work — he has “Product Sync” at 12:30pm and a conflict at 5pm. Want me to book one of these?

One message, and you have your answer instead of converting five times one by one.

Here’s a more realistic scenario where some times do work:

You type:

London office sent availability for the quarterly review:

• Tuesday 3pm-4pm GMT
• Wednesday 10am-11am GMT
• Wednesday 2pm-3pm GMT
• Thursday 11am-12pm GMT

Which work for Michael?

Converting to Eastern:

• Tuesday 10am-11am ET — Michael has “Product Sync” at 10:30am. Conflict.
• Wednesday 5am-6am ET — outside working hours.
• Wednesday 9am-10am ET — Michael is free. Available.
• Thursday 6am-7am ET — outside working hours.

Wednesday 9am-10am ET (2pm GMT) is the only match. Want me to book it?

You went from a list of four times in someone else’s time zone to a booked meeting in one conversation. No calculator, no toggling views, no “let me get back to you.”

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Find Open Slots Across Time Zones

Sometimes you need to go the other direction — you don’t have proposed times, you need to generate them. And they need to work across offices.

You type:

Find 1-hour slots next week where Michael (ET) and the SF team (PT) are both in business hours

Carly figures out the overlap window, checks Michael’s calendar, and proposes times:

Four slots work:

• Monday 1pm-2pm ET
• Wednesday 1pm-2pm ET
• Wednesday 3pm-4pm ET
• Thursday 2pm-3pm ET

Want me to book one of these?

That’s overlap calculation, time zone conversion, and calendar check — done in seconds instead of 15 minutes of tab-switching.

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Convert Time Zones on the Fly

Even outside of scheduling, you’re constantly converting times. A board member in London mentions “let’s talk at half four.” An investor in Tokyo suggests “Tuesday morning our time.” You need to know what that means for your exec, right now.

You type:

What’s 4:30pm London time in Eastern and Pacific?

Carly responds instantly. But the real power is chaining conversions with calendar context:

• “Michael has a 2pm meeting — what time is that for someone in Dubai?”
• “If I schedule something at 8am Pacific, what time is that for Michael?”
• “Convert Michael’s Thursday schedule to Singapore time so I can send it to the Asia team”

That last one is especially useful — instead of converting each meeting individually, Carly reformats the entire day’s schedule in the requested time zone. Copy, paste into an email, done.

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Chain It All Together

The real power is that you can do all of this in one continuous conversation. You don’t need to navigate between features or open different tools. It’s just a chat.

A typical flow might look like:

1. “What’s on Michael’s calendar Thursday?” — You see the full day.
2. “Move the 11am to 2pm” — Carly confirms it’s clear and moves it.
3. “Now place a hold at 11am called ‘Deep work block’” — Filled the gap.
4. “The London team proposed these times: Tuesday 3pm GMT, Wednesday 10am GMT, Thursday 2pm GMT. Which work for Michael?” — Carly converts, cross-references, and tells you Wednesday 5am ET is too early but Thursday 9am ET is open.
5. “Book the Thursday slot. Title it ‘Quarterly check-in with UK team.’ Add a Zoom link.” — Event created, invites sent.

Five requests, one chat window, maybe two minutes total. That same sequence in a traditional calendar app would’ve been a dozen clicks, at least three different views, and a time zone converter tab.

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Set It Up for Multiple Executives

If you support more than one person, just mention whose calendar you’re working with:

• “What’s David’s schedule on Monday?”
• “Find a time when both David and Michael are free for a 1-hour meeting next week”

Set your default calendar so Carly knows whose calendar you mean by default, and override it anytime by specifying a name.

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Teach Carly How Your Executive Operates

Every exec has quirks. Maybe Michael never takes meetings before 10am. Maybe he prefers Zoom for external calls but Google Meet for internal ones. Maybe Fridays are sacred — no meetings, no exceptions.

You can write all of this into Carly’s preferences doc, and she’ll follow it every time without you having to repeat yourself.

Some things EAs typically add:

• Scheduling rules — “No back-to-back meetings. Always leave 15 minutes between calls.”
• Meeting defaults — “External meetings are 30 minutes with Zoom. Internal syncs are 25 minutes with Google Meet.”
• Priority contacts — “If the CEO or CFO needs time, override other holds.”
• Location preferences — “In-person meetings at the downtown office unless otherwise specified. Include the address: 200 Park Ave, NYC.”
• Travel buffers — “Add 45 minutes before and after any in-person meeting.”
• Time zone context — “Michael is ET but travels to London the first week of every month.”
• Naming conventions — “Use the format: ‘Topic — Michael Chen & [Other Person]’ for all 1:1s.”

The more you add, the less you have to specify in each request. Instead of typing “create a 30-minute Zoom meeting and make sure there’s a 15-minute buffer” every time, you just say “schedule a call with Lisa next week” and Carly already knows the rest.

Think of it as onboarding a new assistant — except you only have to do it once and Carly never forgets.

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Getting Started

Chat with Cal is completely free. Sign in, connect the calendars you manage, and start typing.

There’s no training period, no complex setup, and no credit card. If you can describe what you want in a sentence, Carly can do it. The same way your executives fire off one-line requests to you — that’s how you talk to Carly.

You already know exactly what needs to happen with every calendar request. Now you have a free tool that works at the same speed you think.

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