Connecting Calendly
The fastest way to get Riley booking appointments: paste a single link, hit save, done. No API keys, no OAuth dance, no calendar permissions to wrestle with.
When a caller asks to book, Riley says: "I'll text you a link to pick a time that works — what number should I send it to?". Riley confirms the number, sends your Calendly link by SMS, and logs the request on the dashboard. The caller picks their own slot. Two-way calendar reads aren't required.
Use Calendly mode if: you want zero-config booking, you already use Calendly, or you're not ready to give Sidekick calendar access. Use Google Calendar instead if you want Riley to read availability and book directly into your calendar on the call.
Pick the event type you want callers to book
Open calendly.com in another tab and log in. Choose one event type — most service businesses want a single "Service Call" or "Consultation" event with a 30 or 60 minute duration.
- Duration: 60 minutes (covers most service visits)
- Date range: rolling 14 days — not the default 60
- Minimum scheduling notice: 4 hours (avoids same-hour panic bookings)
- Required fields: name, phone, address, brief description
Copy the share link
On the event type page, click Share. Calendly shows three options — you want the first one, Share Link. Copy the URL.
https://calendly.com/yourname/service-call
Paste it into Sidekick
Back in Sidekick, open Settings › Appointment Booking — Calendly. Paste your link into the "Your Calendly booking link" field and click Save Booking Link.
| Field | Your Calendly booking link |
| Format | Must start with https://calendly.com/ |
| Goes live | Within ~30 seconds of save |
| Sent to caller via | SMS from your Sidekick AI number |
Test it from your own phone
Call your business line and say: "I'd like to book an appointment." Riley should confirm a phone number to text, then send your Calendly link within a few seconds. Tap through — make sure the page loads and slots are available.
- Text arrives within 10 seconds of the call ending
- Link opens directly to your event type page
- At least 3 available slots show in the next week
- Booking flow asks for name, phone, and address
Tell Riley how you want bookings handled
Optional but recommended. Open Settings › AI Agent Knowledge and add a line or two to Booking & policy instructions so Riley uses the Calendly link in the right moments.
For routine bookings: text the Calendly link.
For emergencies or "today": never use Calendly — transfer to me.
After hours: say "we'll text you a link to book first thing tomorrow".
Troubleshooting
"Riley didn't send the link"
Check that SMS notifications are enabled on your account — the toll-free SMS sender shares quota with summaries. Also confirm the caller's number wasn't on your block list.
"Caller says the link is broken"
Open it yourself in an incognito window. If it 404s, the event type was deleted or renamed in Calendly. Re-copy the new share link and update Settings.
"No availability for weeks"
Your Calendly date-range setting is too short, or your calendar is genuinely full. In Calendly › Event Type › Availability, extend the rolling window to 14 days.
"I want Sidekick to book the call, not text a link"
That's Google Calendar mode — switch to that instead.