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How to Have AI Schedule Meetings Over Email (Just Cc It)

Published by 3Gen Internet Corporation, maker of OpenAssistant, Skej and AGNT. Comparisons use public documentation, without hands-on testing.

A main email envelope and a smaller copied envelope converging on a highlighted calendar appointment, a looping paper ribbon showing scheduling through correspondence.

The steps below are taken from each vendor’s help pages. We have not run them.

To have AI schedule a meeting over email, connect your calendar, then Cc the assistant on the thread and ask it to find a time. It reads your calendar, offers times, chases replies and sends the invite. OpenAssistant does this and also handles your inbox, research and other tasks.

This guide shows the setup and the first meeting in three tools that work this way:

At the end we cover Gmail’s built-in Help me schedule, which is not an assistant you Cc but may be all you need.

How every Cc assistant works

The pattern is the same in all three:

  1. Connect your calendar so the assistant can see when you’re free and create events.
  2. Set your defaults: working hours, meeting length, video link, buffers.
  3. Write to the other person, Cc the assistant, and ask it to find a time.
  4. It emails options, handles the replies, and sends the calendar invite.

The differences are in calendars supported, how much you can supervise, and what it costs.

Option 1: OpenAssistant

OpenAssistant schedules the same way, and its assistant also handles email, research and other tasks. (OpenAssistant) Its scheduling page says it finds a time that works for five people across three calendars without sending anyone a poll, and proposes times in the other person’s time zone. (OpenAssistant) Its pricing page lists a free Starter plan with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month. (OpenAssistant pricing)

Step 1: Connect your calendar

Calendar permission is required during onboarding; it lets the assistant view, change and create events. Contacts permission is optional and helps it find people’s addresses. (OpenAssistant)

Step 2: Set your scheduling defaults

In Scheduling Settings: working hours by day, time off, video platform and default length, in-person locations, buffers, a daily meeting limit, which calendars count as busy, and plain-English preferences such as “Avoid scheduling external meetings before 10 AM.” Under Follow Ups, set how many times and how often it chases people. (OpenAssistant)

Step 3: Choose how closely you watch

For your first few meetings, set supervision to Supervised so you’re copied on everything. (OpenAssistant) If you want to approve each email before it goes, set the relevant autonomy categories (for example Email Sent From Your Assistant and Calendar Actions) to Manual. (OpenAssistant) OpenAssistant’s changelog says it regrouped these settings, into messages the assistant sends as itself and messages it sends as you, so the labels in the app may differ from the help center. (OpenAssistant changelog)

Step 4: Cc your assistant

Write to the other person, Cc your assistant’s address, and ask by name. OpenAssistant’s own example:

Hi Andy, let’s set up some time to chat. My assistant, Maya, is going to help coordinate. Maya, can you find us 30 minutes for a sales demo sometime next week?

(Lightly edited for punctuation.)

Include the date range, length, and format (Zoom, phone, in person). The assistant replies to confirm, proposes times, keeps going until a time is set, then sends the invite to everyone. Track it under In Progress tasks in the dashboard. (OpenAssistant)

Instructions in the email override your saved defaults for that meeting only, for example “offer 8:30 AM if that’s the only option this week.” (OpenAssistant)

If you schedule for someone else, such as an executive or a client, OpenAssistant has Coordinator Mode. The person you schedule for (the Principal) shares their calendar with you, with “Make changes to events” in Google Calendar or Editor or Delegate access in Outlook. You then open app.openassistant.us/coordinator, add the Principal’s email and name, and the Principal approves a verification email. Your assistant then works from the Principal’s calendar, availability and meeting settings. (OpenAssistant)

Option 2: Skej

What you need

Skej works with Google Workspace and Microsoft Outlook calendars, and you can connect several. (Skej)

Plan check: new accounts start on a 7-day Premium trial that ends after 7 days or 3 booked meetings, whichever comes first. After that, the Free plan includes a booking link but no use of Skej assistants, so Cc scheduling needs Pro ($15 per user per month billed annually, $19 monthly) or Premium ($23 annually, $29 monthly). (Skej)

Step 1: Connect your calendar and pick a default

Sign up with your Google or Outlook account; Skej checks that calendar by default. To add more, go to Connections. Then open the calendars tab, select every calendar Skej should check for conflicts, and choose a Default Calendar where it creates events. (Skej)

Step 2: Set your defaults

Do this in the dashboard, not by email. Skej’s docs say requests like “never schedule me on Fridays” sent by email only apply to that one meeting. Lasting rules go in settings or under Instructions. (Skej)

Step 3: Cc Skej on your first thread

  1. Email the person you want to meet. Make sure you’re on the thread; Skej only acts for a user who is included. (Skej)
  2. Cc skej@skej.com. (If you picked another assistant, use its address, for example lexy@skej.com.)
  3. Ask it directly, with the details: “Skej, can you help us book 30 minutes next week? Hana is in London.”

Skej replies with times based on your calendar and preferences, labeled with a time zone. The other person picks one or asks for others, and Skej sends the invite once a time is agreed. Tell it when people are in different time zones. (Skej)

Send from an email address connected to your Skej account. System assistants only reply to addresses they recognize as yours. (Skej)

Step 4: Reschedule or cancel

Reply in the same thread or email Skej directly: “Skej, can you reschedule this meeting to next week?” It proposes new times or cancels, then updates the invite. (Skej)

Supervision: by default Skej Cc’s you on every message. On Premium, Unsupervised Mode (on the Defaults tab) Bcc’s you on its first reply and then takes you off the thread. (Skej)

Option 3: Howie

What you need

Howie’s help center describes connecting a Google Calendar only; it does not mention Outlook. (Howie) Pricing on its homepage: a Team plan at $25 a month with credits, and $25 in free credits to start. (Howie) Its help center FAQ says “We don’t do free trials” and describes Basic and Pro plans instead, so check the homepage before you sign up. (Howie FAQ)

Steps

  1. Connect your calendar: go to Add Calendars and click Add Google Calendar.
  2. Set preferences: go to Edit Preferences for working hours, meeting rules and locations.
  3. Cc Howie: add howie@howie.ai or howie@howie.com to the To or Cc line, and ask, for example “+Howie to find us 45 minutes with Alex and Priya in the afternoon.”

(Howie)

Howie suggests times and books the meeting once someone confirms. If you don’t give a length, it uses your default. To move a meeting, ask in the thread: “can we push this back 30 mins?” (Howie)

Follow-ups and supervision: after sending options, Howie waits 24 hours and then asks whether you’d like it to follow up. You can change that by email, for example by telling it to follow up with guests automatically without checking with you. (Howie)

Limits Howie lists: it can’t handle all-day events yet, can only reschedule events it created or you made in Google Calendar, and threads it starts with new contacts may land in spam, so Howie suggests you send the first email and Cc it. (Howie, Howie FAQ)

On Howie Pro you can set up an assistant on your own domain: Assistants, then + New Assistant. Howie’s homepage lists this as a $20 a month add-on. (Howie Pro)

Don’t need an assistant? Gmail’s Help me schedule

If you only want to offer times in an email you’re writing, Gmail can do that. Google’s help page says it needs an eligible Google Workspace or Google AI plan; its feature table lists Workspace only, in English, in the US. (Google)

  1. In Gmail on a computer, write or reply to an email with your recipients.
  2. Click Help me schedule at the bottom (or More options, then Help me schedule).
  3. Review the suggested times and click Send.

The recipient picks a time and books it. Up to 20 guests. (Google) It doesn’t chase people or negotiate; you’re still the one following up.

Which one to use

OpenAssistant Skej Howie
Calendars (per docs) Google, Microsoft, Apple Google, Outlook Google
Address to Cc Your assistant’s address skej@skej.com or chosen assistant howie@howie.ai or howie@howie.com
Auto follow-ups Yes, you set count and frequency Yes, you set timing and count Asks you after 24 hours by default; can be automatic
Approve each email first Yes, Manual autonomy Not stated Not stated
Stay off the thread Unsupervised mode Unsupervised Mode (Premium) Not stated
Work beyond the calendar Yes (email, research, tasks) Calendar-focused (plus daily agendas, reminders) Calendar-focused (plus reminders, calendar questions)
Price to Cc it Free Starter plan; Pro from $60 per user per month billed annually (per-user pricing confirmed by 3Gen) Pro from $15/user/mo (annual) Team plan $25/mo with credits (homepage)

(Sources linked above)

Our read: start with OpenAssistant if you want one assistant for scheduling plus inbox and other work. It is the only one of the three whose docs describe approving each email before it sends. If scheduling is the whole job, Skej and Howie are the focused choices. Skej documents Outlook support and Howie’s help center doesn’t, so Outlook users who want a scheduling-only tool should look at Skej. If you’re on Google and want a non-3Gen option, Howie’s docs are clear and its homepage advertises $25 in free credits.

Check it yourself

This section is advice for you. We have not run these checks.

Run the same three scheduling jobs in each tool, from a fresh thread each time:

  1. One outside person, same time zone: 30 minutes next week. Good sign: the invite lands with the right length and video link.
  2. Two outside people, different time zones: 45 minutes. Good sign: every proposed time is inside everyone’s working hours.
  3. Silent guest: don’t reply as the guest. Good sign: the assistant follows up on the schedule you set and then tells you.

FAQ

How do I get AI to schedule a meeting over email?

Connect your calendar and set your defaults, then write to the other person, Cc the assistant and ask it to find a time. The assistant emails options, handles the replies and sends the invite once a time is agreed.

Can I approve each email before it goes out?

OpenAssistant’s docs describe it: set the relevant autonomy categories, such as Email Sent From Your Assistant and Calendar Actions, to Manual. Skej and Howie’s help pages do not describe per-email approval.

Which of these work with Outlook?

Skej documents Google Workspace and Outlook calendars. OpenAssistant supports Google, Microsoft and Apple calendars. Howie’s help center describes Google Calendar only.

What happens if the other person does not reply?

OpenAssistant lets you set how many times and how often it follows up. Skej lets you set the timing and number of follow-ups and tells you after the last one. Howie waits 24 hours and then asks whether you want it to follow up, unless you tell it to do so automatically.

What does it cost?

OpenAssistant has a free Starter plan with 1,000 credits at signup, plus 100 bonus credits a day once those are used up, up to 1,000 a month. Skej Pro is $15 per user per month billed annually. Howie’s Team plan is $25 a month with credits, per its homepage.

Try OpenAssistant

To hand off scheduling and the rest of your inbox to one assistant, Try OpenAssistant. Set supervision to Supervised for your first few meetings so you are copied on everything, and see plans on the pricing page. If scheduling is all you need, Try Skej, which has processed millions of meetings.

Sources