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Calendar Integration: Booking Appointments Through Your AI Agent

Written by Nikita Podelenko
Updated this week

Calendar Integration: Booking Appointments Through Your AI Agent

Connect your calendar to SkipCalls and your AI agent can check your availability and book appointments during phone calls — no back-and-forth emails needed.

Supported Calendars

  • Google Calendar — Full integration. Your agent can check availability, create events, and send calendar invites to guests.

  • Microsoft Outlook — Full integration. Works with both personal Microsoft accounts and work/school (Microsoft 365) accounts. Your agent can check availability, create events, and send calendar invites.

  • Calendly — Works with your Calendly event types. Requires a paid Calendly account (free accounts are not supported). The agent will ask callers for their email before booking.

  • Square Bookings — Works with Square appointments. After connecting, you pick which location and services to use.

  • Cal.com — Coming soon.

Connecting Your Calendar

  1. Go to Appointment Booking Systems in the dashboard.

  2. Click Connect Calendar and choose your provider.

  3. Sign in with your calendar account and grant access.

  4. Your calendars will appear on the page.

Extra Step for Square

After connecting Square, you'll also need to:

  1. Select your business location.

  2. Choose which services to import (e.g., "Haircut - 30 min").

  3. Click Import.

Note for Outlook

When connecting Outlook, you'll sign in through Microsoft and grant SkipCalls permission to read and write calendar events. This works with both personal Microsoft accounts (Outlook.com, Hotmail, Live) and work/school accounts (Microsoft 365, Office 365). Only calendars you can edit will be imported.

Linking a Calendar to an Agent

Connecting a calendar to your account doesn't automatically enable it for your agents. You need to link it to each agent that should use it:

  1. Find the calendar on the Appointment Booking Systems page.

  2. Click Connect to Agent and pick the agent.

  3. Or go to the agent's settings and open the Calendars tab.

Default availability is set to Monday-Friday, 9 AM - 5 PM, 30-minute appointments with 15-minute gaps between them. You can customize all of this.

Availability Settings

Each agent-calendar link has its own schedule. You can adjust:

  • Work Days — Which days appointments can be booked.

  • Work Hours — Start and end times for each day. You can set different hours for different days.

  • Appointment Length — How long each appointment is (5 to 120 minutes).

  • Gap Between Appointments — Padding between appointments to avoid back-to-back bookings (0 to 60 minutes).

  • Timezone — Your browser's timezone is used by default.

  • Instructions — Private notes for the AI (e.g., "Only book consultations in the morning"). These are never shared with callers.

  • Active / Inactive — Turn booking on or off for this calendar.

What Happens During a Call

When a caller asks to schedule an appointment, here's what your AI agent does:

  1. Checks your calendar — It looks at your real availability, including existing events, work hours, and gaps.

  2. Suggests a time — "I see 3 PM on Tuesday is available. Would that work?"

  3. Collects details — Asks for the caller's name (and email for Calendly).

  4. Books it — Creates the event on your calendar once the caller confirms.

  5. Confirms — Tells the caller the appointment is booked.

If the requested time isn't available, the agent suggests the next open slot — searching up to 14 days ahead.

Without a calendar connected, the agent will simply take a message about the scheduling request and pass it to you.

After a Booking

When an appointment is booked, you'll be notified in several ways:

  • The event appears in your connected calendar (Google, Outlook, Calendly, Square, etc.).

  • If the caller gave their email and you use Google Calendar or Outlook, they'll get a calendar invite.

  • You receive an email with the appointment details.

  • You get a push notification on your phone.

  • The appointment shows up in your SkipCalls dashboard under Upcoming Appointments.

  • You can also see bookings directly on each call's detail page.

Viewing Appointments

The Appointment Booking Systems page shows your upcoming appointments at the top, including the guest's name, date, time, how it was booked (call or SMS), and a link to the original call.

You can also see appointments on the call detail page — any bookings made during a call will appear with the provider, date/time, and guest info.

Reconnecting

If your calendar connection expires, you'll see a yellow alert. Click Reconnect to fix it. SkipCalls also refreshes connections automatically to prevent this.

Removing a Calendar

Click the trash icon on any calendar card to disconnect it. This only removes it from SkipCalls — your actual calendar and events stay untouched.

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