Best tools for finding a time for 5 or more people
The short answer
For more than four or five people, consider a poll if you want everyone to mark their availability directly. Everyone marks when they’re free, and you pick the winner. Polls work even when you can’t see anyone’s calendar.
AI tools help in two cases:
- Everyone is inside your company and on the same calendar system. Then a tool can read free/busy and book without asking anyone.
- A few external people need chasing. An assistant you cc can follow up with the slow responders while everyone else’s time is held.
Options to consider:
- A group where you’d rather not send a poll: OpenAssistant, an assistant you cc that says it finds a time for five people across three calendars and keeps going until everyone has agreed.
- Mixed internal and external group, any calendar: Doodle, or Calendly meeting polls.
- On Microsoft 365: Outlook Scheduling Poll, which is already included.
- On Google Workspace: Gemini’s “Help me schedule,” for up to 20 guests on eligible plans (US English, web only for now).
- Free and no sign-up: When2meet or Rallly.
Our ranking
Based on published group features and limits, considered qualitatively for this use case. Doodle ranks first as a poll option. OpenAssistant ranks second: it is the one assistant here that says it handles group scheduling without a poll and chases slow responders, and polls beat it only on cost and published limits.
1. Doodle: the group poll, with invites
- How it works. Pick candidate times, share one link, confirm the winner, and Doodle sends calendar invites to respondents (Doodle polls). It converts times to each person’s time zone (Doodle help).
- Free plan. “One Group Poll,” limited to 10 time slots, with ads.
- Price. Team is $16 per seat per month on annual billing (Doodle premium).
- Calendars. Google Calendar, Microsoft Outlook 365 and Apple iCloud, per Doodle’s integrations help (Doodle integrations help).
Falls short on: the free plan allows only one poll.
2. OpenAssistant (our product): an assistant that chases the group
- Claims. It says it “Finds a time that works for five people across three calendars without sending anyone a poll,” and keeps negotiating “until there’s one time everyone has agreed to” (OpenAssistant scheduling, OpenAssistant scheduling FAQ).
- Where it works. Email, text, Slack or in the app (OpenAssistant pricing FAQ).
- Free credits. Starter is free 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).
Where others do better:
- Evidence. The five-person example is the vendor’s own marketing, and it states no maximum group size. A published poll tool shows its limits.
- Cost. Its pricing page says coordinating a meeting across multiple people can use “hundreds” of credits (OpenAssistant pricing). A free poll costs nothing.
Why we recommend trying it: when some of the group are outside your company and slow to answer, a poll link gets ignored, and an assistant follows up for you on a cadence you set. Starter is free to try.
3. Calendly meeting polls and collective events
- Polls. “Every Calendly plan includes access to the scheduling poll feature” (Calendly meeting polls).
- Collective events. These show only times when every host is free. They’re useful for recurring internal panels (Calendly event types). Multi-person event types need a paid plan, from $10 per seat per month on annual billing (Calendly pricing).
Falls short on: Calendly’s AI assistant, Callie, is in beta and handles one-on-one meetings only (Calendly AI assistant).
4. Outlook Scheduling Poll: free if you have Microsoft 365
- How it works. Up to 15 time options. People outside your organization vote through a secure link, and Outlook places temporary holds for each option (Microsoft support).
- Limits. It doesn’t work on personal Outlook.com or Gmail accounts (Microsoft support). It doesn’t work with shared accounts or group calendars, and delegates can’t create polls.
- Copilot isn’t the tool for big groups: chat scheduling handles “up to two other people” (Copilot FAQ).
5. Gemini “Help me schedule”: for Google Workspace
- Groups. It expanded from two people to multiple guests in February and March 2026 (Google Workspace Updates). Up to 20 guests, with 4 proposed slots by default (Gmail help).
- Who gets it. It needs an eligible Workspace or Google AI plan, and Gmail’s feature table lists it as English, US only, on the web (Gmail Gemini features).
Falls short on: it suggests times based on availability Google can see. External guests on other calendar systems may not show up.
6. Rallly: free, open-source polls
- Free plan. Up to 3 open polls, unlimited participants, and inactive polls deleted after 30 days.
- Pro. $6 per seat per month billed yearly ($72 a year per seat) (Rallly pricing).
- Self-hosting. You can self-host it.
7. When2meet: free grid, no accounts
- What it is. “When2meet is a free service,” supported by ads (When2meet). People paint their availability on a grid. Its pages list no calendar integration, so people fill it in by hand.
8. SavvyCal polls
- How it works. Results “rank every time by how many people can make it,” and voters can overlay their Google or Microsoft calendar on the poll (SavvyCal polls). Polls are free; scheduling links need a paid plan from $10 per user per month on annual billing (SavvyCal pricing).
9. Clara: an assistant that chases everyone
- How it works. Clara says it contacts all participants, tracks responses, follows up, and confirms once a time works (Clara).
- Price. $80 a month for 30 meetings (Clara pricing).
10. Skej (our product)
- Internal groups. For teams where everyone uses Skej, Autobook “works with any number of people” and books instantly from everyone’s calendars and preferences. For mixed groups it first finds times that suit the Skej users, then offers them to the others (Skej Autobook help).
- Price. Pro is $15 per user per month on annual billing (Skej pricing).
Where others do better:
- Mostly external groups. A poll is simpler and free.
- No group texts. Skej’s text and WhatsApp channels don’t support group threads or group scheduling (Skej boundaries).
- Every user needs a seat. Autobook’s instant booking only works if everyone on your team is signed up with Skej, and each team member is billed (Skej pricing FAQ).
Also worth knowing
- Reclaim Smart Meetings are “designed for meetings with up to 5 attendees” (Reclaim 2.0 FAQ), so they’re not built for large groups.
- Howie’s undated documentation calls its group scheduling “pretty limited” and says it “will accept the first time that anyone on the thread agrees to” (Howie docs). Its current homepage claims better group handling.
- Sarra caps group size by plan: up to 5 attendees on Gold and 10 on Platinum, per its FAQ (Sarra pricing).
Comparison table
| Tool | Max group stated | Works with external people | Needs others’ calendars | Free option |
|---|---|---|---|---|
| Doodle | No limit listed (10 slots on Free) | Yes | No | 1 poll |
| Calendly polls | No limit listed | Yes | No | Yes |
| Outlook Scheduling Poll | No limit listed (15 options) | Yes, via link | No | With M365 work account |
| Gemini Help me schedule | 20 guests | Yes | Uses what Google can see | With eligible plan |
| Rallly | Unlimited participants | Yes | No | 3 open polls |
| When2meet | No limit listed | Yes | No | Free |
| SavvyCal polls | No limit listed | Yes | Optional overlay | Polls free |
| Clara | No limit listed | Yes | No | Trial: 5 meetings in 14 days |
| OpenAssistant (ours) | No limit listed (marketing example: 5 people) | Yes | When it has access | 1,000 credits at signup, plus 100 bonus a day |
| Skej (ours) | Any number of internal Skej users | Yes, via email | Teammates must use Skej | Link only |
Related reading
- AI tools for scheduling across time zones: Calendly is the best link for detecting a guest’s zone; Vimcal is best if you live in several zones.
- AI scheduling assistants you cc on email: Ranks the assistants you copy on a thread, including Blockit, Howie and Clara.
- Scheduling links vs AI assistants: When a link is better, when an assistant is better and when to use both.
- AI for board meeting prep: A board cycle stage by stage, with what to hand over and the confidentiality rules.
- How EAs use AI to support several executives: A step-by-step playbook for assistants who support more than one executive.
Frequently asked questions
What is the best way to find a time for 5 or more people?
A poll is an option: everyone marks when they’re free and you pick the winner. If you would rather not send a poll, an assistant you cc such as OpenAssistant can email the group and follow up with slow responders.
How many people can Gemini schedule with?
Gemini “Help me schedule” in Gmail supports up to 20 guests and proposes 4 slots by default, on eligible Workspace and Google AI plans. It is English, US only, on the web.
Is there a free tool for group scheduling?
Yes. When2meet is free and needs no sign-up. Rallly’s free plan allows 3 open polls with unlimited participants. Doodle’s free plan allows one group poll. Calendly meeting polls are on every plan.
Can an AI assistant schedule a large group?
OpenAssistant says it handles group meetings across time zones and calendars. Calendly’s Callie is one-on-one only, and Reclaim’s Smart Meetings are designed for up to 5 attendees.
Try OpenAssistant
For a group that won’t answer a poll, try OpenAssistant and let it chase the replies. Starter is free, and plans are on the pricing page.