Best AI assistants to book a 3-person meeting across time zones

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

OpenAssistant is our recommendation for booking a three-person meeting across time zones. Its page says it will “negotiate across time zones, chase people who go quiet, and send the invite”, and you can cc it, email it or text it. Skej, also ours, and Howie document the same core behavior at a lower list price.

Booking one meeting with three people in three cities is the job every scheduling assistant claims to handle. It is also where a lot of them quietly hand the work back to you: they suggest a time, and then you send the email, read the replies and chase the person who went quiet. This article compares what ten products say publicly about the whole job, start to finish: one instruction, two outside people, a few awkward replies, and a calendar invite at the end.

The job

This is Job 1 in our evaluation framework, plus the rule-keeping question from Job 4.

A typical version of the job. You are in New York. The other two people are in London and San Francisco. You want a 45 minute video call in the next five business days. You protect a lunch hour and keep working hours of roughly 9:30 to 6:00.

With normal clocks, the only window where New York, London and San Francisco workdays (9:00 to 6:00 local) all overlap is 12:00 to 1:00 Eastern, which is 9:00 to 10:00 in San Francisco and 5:00 to 6:00 in London. Add a protected lunch that starts at 12:30 and a 45 minute call no longer fits. A good assistant has to notice that and do something sensible, such as ask whether lunch can move, propose a shorter call, or ask someone to stretch their day, rather than blindly picking “a time everyone is free”.

What to look for in a vendor’s documentation:

1. Does it negotiate with the outside people directly, by email or text, or does it only suggest times to you?
2. Does it respect your working hours, buffers and protected blocks, and say what it does when no slot meets every rule?
3. Does it write proposed times in each recipient’s own time zone, or name the zone?
4. Can it handle a reply such as “Thursday is out for me” without coming back to you?
5. Does it follow up with someone who goes quiet, and does the vendor say how often?
6. Does one calendar invite reach all three people, with a video link and the right length?
7. Does it confirm the final time to you?
8. Does it hold your standing rules when an outside person asks for a time that breaks them? This is Job 4. The vendor’s pages should say what the assistant does without asking you first, and whether you can require approval.

A documentation point about clock changes. The UK and the US move their clocks on different dates. UK clocks go back on 25 October 2026 (gov.uk) and US clocks go back on 1 November 2026 (NIST). In the week of 26 to 30 October, London is four hours ahead of New York instead of the usual five. If you schedule across the Atlantic in a week like that, check whether the vendor’s pages say anything about daylight saving differences. In this set, Skej lists “Time Zone Management” on Pro and up (Skej pricing), and Blockit’s homepage lists clock changes among the situations it handles (Blockit). The other pages cited here do not describe how they handle the gap.

The 10 assistants

We picked ten products that say they can schedule meetings with other people, or that sit inside the mail and calendar most people already use. Facts below are from each vendor’s own page.

Left out, and why:

• Calendly’s Callie “works for one-on-one meetings only” right now, per Calendly’s own page (Calendly). This is a three-person job.
• Reclaim is built around calendar automation, scheduling links and a chat assistant. Its page does not describe an assistant you copy on an email thread with outside people (Reclaim).
• Clockwise shut down on 27 March 2026, per its own homepage (Clockwise).
• Personal agents like Poke, Instinct and Meta Muse are covered on their own terms in our roundup.

Settings that change how hands-off a product is, as the vendors document them:

• Town defaults to asking before it emails anyone, but offers an “Allow all actions” mode (Town docs).
• OpenAssistant offers an “Autonomous” mode (OpenAssistant).
• Skej’s unsupervised Bcc mode is Premium only (Skej pricing); on Pro the standard cc mode applies.
• Howie names Gmail and Google Calendar, and its homepage does not mention Outlook (Howie). Clara, Blockit and Copilot name Outlook or Microsoft calendars; check calendar support against the account you use.
• Gemini, Copilot, ChatGPT and Claude do not have their own email addresses on the pages cited here. You give the instruction in each one’s chat or side panel. Where a product only drafts an email for you to send, the outside back and forth stays with you.

Who documents what

This is an editorial ranking of how fully each group’s public pages cover the job, using the criteria in the framework: documented coverage, what the vendor says about results, price, where it works, and privacy and admin controls.

1. OpenAssistant first, then Skej, Howie, Clara and Blockit. All five say they handle the back and forth and chase quiet people. OpenAssistant is the pick: its page names negotiating “across time zones” and a follow-up cadence you set, and you can reach it by cc, email or text. Skej documents time zone management as a named feature, and Blockit documents Slack threads. Where competitors do better: Skej Pro lists at $19 a month billed monthly and Howie starts at $25 in credits, both cheaper than OpenAssistant Pro at $72 per user per month billed monthly, Clara at $80 for 30 meetings and Blockit Lite at $145 billed monthly. If price decides it, start with Skej or Howie.
2. A general assistant with scheduling built in: Town. It has its own address and handles invites, but asks before every email by default, which is safer but slower unless you loosen it. Town’s pages cited here do not state a follow-up promise for people who do not reply.
3. Built-in suggestions: Gemini in Gmail and Copilot in Outlook. Both suggest times. Neither page cited here documents emailing outside people, reading their replies or following up, so that part stays with you. Copilot’s page limits the suggestion to up to two other people, which fits a three-person meeting exactly and no more.
4. General agents with connectors: ChatGPT with Work and Claude with Cowork. Both can reach Gmail and Calendar. The pages cited here do not say whether either can run a multi-day negotiation with outside people unprompted, so they sit last on documented coverage. Both list at $20 a month, and you may already pay for one.

Related reading

• Best AI assistants to reschedule a meeting (8 compared): eight products compared on rescheduling, running late and holding your rules.
• Why we recommend OpenAssistant, with 11 alternatives compared: twelve assistants ranked on documented jobs, price, channels and privacy.
• How to Have AI Schedule Meetings Over Email (Just Cc It): steps for OpenAssistant, Skej and Howie, plus Gmail’s Help me schedule.
• How to Give an AI Assistant Calendar Access Safely: read or write access, least-access setup and how to take access back.

Frequently asked questions

Can an AI assistant book a meeting with people in three time zones?

Several say so. OpenAssistant’s page says it will “negotiate across time zones, chase people who go quiet, and send the invite”. Skej, Howie, Clara and Blockit also document handling the back and forth by email.

Which AI assistant is best for scheduling across time zones?

OpenAssistant, because its page names time zone negotiation and a follow-up cadence you set. Skej lists “Time Zone Management” on Pro and up at a lower price.

Do ChatGPT, Claude, Gemini or Copilot book meetings with outside people?

The pages cited here do not say they email outside people and follow up. Gemini in Gmail and Copilot in Outlook suggest times, and Copilot limits that to up to two other people.

How much do AI scheduling assistants cost?

Skej Pro is $19 a month billed monthly, Howie starts at $25, Town Pro is $59, OpenAssistant Pro is $72 per user per month billed monthly ($60 annually), Clara is $80 for 30 meetings and Blockit Lite is $145 billed monthly.

Try OpenAssistant

Give OpenAssistant the instruction, cc it on the thread and let it negotiate the time. Try OpenAssistant free with 1,000 credits at signup, or see the pricing. Want a lower-priced scheduler? Skej, our other product, has processed millions of meetings.