Allowing callers to schedule appointments via conversational AI?

[Swetha29]

Hello!

I am curious to know if any one here has to deal with customers calling in to schedule appointments? Especially if they are reaching out to you for the first time.

How do you feel about an AI virtual assistant having a conversation to find the right time + location and scheduling it directly on the Square Appointments platform?

[Studio86]

I think that would be awesome and to have a way to accepts deposits as well. 

[Emasbeauty]

If you use square and go into the system you can now take 50% upon online bookings and what I do for in person is take a booking fee there and then, and over the phone I send an invoice and once paid I book them in 

[Swetha29]

Do you send them the invoice via email or SMS? Is it a Square link?

[Emasbeauty]

I send via sms mostly and it works well and my clients don’t have an issue and the ones that don’t pay don’t get booked in. 

[Swetha29]

We currently don't accept deposits but we can schedule and manage an appointment with an AI bot. The application also offers other traditional telephony services like call routing, forwarding, voicemail etc. https://squareup.com/us/en/app-marketplace/app/telekit

[Emasbeauty]

I’m currently in the UK and can honestly say never will I use AI to replace speaking to customers. My business is heavily customer based and most do book online. The few that still ring I’m happy to speak with. AI isn’t human and I certainly wouldn’t let it replace me. Having conversations and building trust with potential new clients is important to me and my brand massively 

[Swetha29]

That makes sense. I figured some business owners would prefer to answer the call themselves. 

[sacredheart926]

We use an AI answering system to assist when we’re busy or unable to answer the phone, as well as after hours. It provides me with a transcript of each call so nothing is missed. That being said, I personally return every call, as building and maintaining a strong relationship with our customers is very important to me! 

[alejandro-ref]

Great question — and this is exactly the problem I've been building for.

I'm the founder of FrontdeQ (frontdeq.com), an AI voice receptionist built specifically for Square merchants. It answers the phone, has a natural conversation with the caller, checks real-time availability on Square Appointments, and books directly into your calendar — staff, service, location, all of it.

A few things we've learned so far:

• First-time callers want to finish the booking in one call — voicemail = lost booking.
• Tone matters more than script. Robotic = instant hang-up.
• Deep Square integration is the moat. Generic phone bots create calendar chaos because they don't actually know your availability.

We're in early-access mode right now and I'm giving the first users 3 months free in exchange for honest feedback. If you want to be one of them, let me know — happy to set up a demo call and walk you through a real booking flow.

[Sheli]

AI is here and we will be seeing more and more AI answering services. That makes me NOT want to use it. We use an answer service. I want to maintain human connection as much as possible. 

[TCSlaguna]

We would be open to it. There are times our cashiers miss a phone call because they are ringing up customers. Booking appointments over the phone takes a long time. 

[Swetha29]

@TCSlaguna Thanks for getting back to me. We have that available if you would like to try it out. We are working to reduce the time it takes for the AI assistant to respond (it's a bit slow). I'd be happy to hop on a call and give you a demo as well. https://squareup.com/us/en/app-marketplace/app/telekit