Interacting with the AI Scheduler

Available on these plans
  • Free
  • Teams
  • Business
  • Enterprise

Note: AI Scheduler is currently in open Beta. AI Scheduler will remain a free feature until Generally Available.

In this article:



Whether you’re looking to reschedule a meeting, find the perfect spot to fit in a Focus Time hold, or spinning up a new Scheduling Link to send out in an email exchange, Clockwise’s AI scheduler can help – and take the time and stress out of setting everything up for you.


What type of tasks can AI Scheduler make easier for me?

  • Basic scheduling: Schedule, reschedule, and cancel one-time or recurring meetings via conversational chat.
  • Bulk scheduling: The ability for a user to take action on multiple meetings at once (includes scheduling, rescheduling, other updates).
  • Fix conflicts: Users can ask AI Scheduler to help them fix their meeting conflicts, and AI Scheduler will highlight the conflicts in the calendar and provide smart rescheduling suggestions
  • Create Scheduling Links: Create Scheduling Links via chat. Streamline the scheduling process by having AI Scheduler generate links on your behalf. Quickly share custom Scheduling Links.

Engage with our AI

Working with AI Scheduler is a lot like working with an assistant – it’s quick, understands conversational language, and can make a lot of connections you’ll no longer need to keep track of yourself. You can find a list of prompts here, but here’s a few to get started:

  • Schedule a 30 min sync on Thursday or Friday with Gary.
  • Set up a recurring 1:1 with Abou every other week on Tuesday.
  • Make me OOO tomorrow afternoon and reschedule my afternoon meetings.
  • Fix my conflicts next week
  • Create a 15 minute link with my and Nikita’’s availability on Tuesday and Thursday

If you’re not sure what AI Scheduler can help you with we’ve made it easy for you to get started. You can directly ask it for help or scheduling advice.

  • Try How should I use you? Or Which meetings should I mark as flexible?

Pair prompts together 

You can push several commands together, as you would when speaking with someone.

For example, you can ask AI to Reschedule my meeting with Jin tomorrow and schedule a meeting with Kacy tomorrow, or Cancel my meetings tomorrow and schedule a 1 hour hold to review the board deck.

Use the calendar view

The AI Scheduler lives side-by-side with an overview of your calendar.

If you prefer to perform changes visually rather than by chat first, you can initiate a rescheduling flow by clicking on any event in the calendar. This will open a menu that allows you to choose to Reschedule with AI.

Make a calendar change

When you want to make a direct calendar change using a prompt, you’ll collaborate with the AI Scheduler. You’ll prompt what you want to happen, AI will respond with a proposal to you detailing what its actions will be if you approve of them, and then you confirm whether you’d like those changes to happen. If you confirm, the changes will happen within the minute, and if you select cancel, no changes will occur around what you prompted.

Note: If you do not own edit permissions for a meeting, Clockwise will inform you that you have a conflict that it is unable to reschedule. You will then be given the option to accept the changes AI Scheduler can perform, or to cancel all changes. If you confirm these changes, AI Scheduler will change what it has permission to change and other conflicts will need to be manually resolved.


Note: Nothing will change on your calendar until you explicitly confirm it within the chat by clicking the options presented to you. A confirmation message will follow your choice.

If you’re unsure what seems the most convenient of the times offered by AI, you can collaborate with folks by sharing the times that would work best for all all Clockwise users – this will share all the times that AI uncovered as workable for the collaborators who have not responded no to the event RSVP. Click Share times to create a comprehensive scheduling proposal that you can then share in a chat message or email.

Create Memories

AI Scheduler can store your scheduling preferences and key facts about your teammates and colleagues. This lets Clockwise know how you like things scheduled to make all scheduling tasks made through the AI interface faster in the future. You can use the @ symbol in chat to specify a person or an event.

  • Create an alias for a group of people
    • My team is Dillon, Krishnan, and Sam
    • The People Team is Chelsea, Flora, and Peter
  • Create meeting templates
    • Whenever I schedule with Vicky, add [insert link] to the description of the meeting

Note: Memories stored by AI Scheduler do not affect anything else in Clockwise, they only affect the suggestions created within AI Scheduler. For example, if you submit I prefer my Focus Time to be scheduled in the afternoon as an AI memory, it will not change your overall Focus Time scheduling preference in Your Ideal Day.