Calendly Assist - Conversational Scheduling (via chat) for one-offs

Calendly Assist functionality is used to create one-off meetings using natural language processing (NLP). One-off meetings offer a quick and flexible way to create a one-time meeting that doesn't match your regular schedule. 

Before you begin:

Calndly Assist functionality is powered by OpenAI and through contract agreement, OpenAI does not train on customer data. The input data submitted through Calendly Assist functionality is used solely to generate a response from the AI model and provide that response back to the user. The input data submitted is not used for model training, and content and usage data will be used according to Calendly's Privacy Policy and Beta Terms of Use.


Calendly Assist functionality is currently in Beta and is continually evolving. As a result, there may be instances where the requested meeting setup may not entirely match the prompts given. In the event that this occurs, we have ensured that manual edits can be made when needed.

How to get started

  1. Select the Schedule with AI Beta flag from your Calendly homepage.
    Schedule with AI Beta Tag.png

  2. Enter details about the type of meeting you're looking to schedule within the conversational scheduling window.
    • AI recommends meeting details available to use or you can add your own.
    • Recommended inputs when adding your own meeting details include:
      • Meeting type (i.e. coffee chat, product demo, review meeting)
      • Meeting date (i.e. this Friday, November 27th, next Thursday)
      • Meeting duration (i.e. 30 minutes, 1 hour, 2 hours)
      • Meeting location (i.e. Zoom, in person, conference room B)

  3. Review the meeting details and availability options generated by the AI bot within the calendar view.
    • Adjust your event name, duration and location under Meeting details.
      Calendly Assist Meeting Detail Changes.gif

    • Edit availability to either remove or add times.
      • Remove times from your one-off availability schedule by selecting x.
      • Add additional time options by selecting other dates and times from the availability view.
        Conversational Scheduling Adjust Available Times.gif
  4. Confirm your meeting details and available times to begin sharing your scheduling link.

Share your new scheduling link

With our Calendly Assist scheduling feature you can share your scheduling link one of two different ways:

Copy & paste link to communication channels
Copy your one-off scheduling link from within your conversational scheduling view or from within your scheduled events tab:

  • Copy link from Calendly Assist Meeting details view
    Copy link for AI scheduling.png

  • Copy link from your Scheduled events tab under Pending
    Copy conversational scheduling link from scheduled events tab.gif

Draft an email invitation
Share your one-off meeting scheduling link by sending an email invitation directly from within Calendly using the Draft invitation button:

  • Add your invitee information then draft an email to be sent from
    Draft email invitation via Calendly Assist.gif

  • Once you have sent your email, choose one of the following options:
    Calendly Assist steps after creation.png
    • I'm done for now
      • Selecting this button will take you back to your Calendly homepage.
    • Schedule another meeting
      • Selecting this button will take you back to the beginning of the conversational scheduling flow to create another meeting.