Oh! That’s a super interesting question @Cuizien.

If you’re alright asking questions outside of Calendly (ie, a Google Form, Typeform, etc.) you could use a Workflow to send out a link to the form. There a ton of different options in triggers, timing, etc., so check out more on Workflows here. The other nice part about this is that it gives you way more types of questions, formats, etc. you can ask and utilize.

Hope that helps!