Look into Street Epistemology[1]. Anthony Magnabosco on YouTube[2] is a good start.

Essentially, be interested and pose non-confrontational questions regarding the other person’s belief. Don’t argue for your point, have them explain theirs. If you ever reach a moment where the other person says “good question, I hadn’t thought of that”, stop the conversation. Let them mull it over in their own time, your job is done. You may or may not pick up the conversation another day, and either is OK.

Teach someone else this skill and you’ll have conversations where both parties are striving to understand each other instead of pushing their own agenda.

[1]: https://en.wikipedia.org/wiki/Peter_Boghossian#Street_episte...

[2]: https://www.youtube.com/channel/UCocP40a_UvRkUAPLD5ezLIQ

I would start with Plato. While the works are literary and not verbatim transcriptions of conversations, I think it gives a good view into the process of asking questions to dig into a point, then backtracking.

What you rapidly realize when applying this (as GP alludes to) is that most people simply aren't interested in the protracted examination of an idea. The challenge is to find people who are have interesting thoughts and the patience to work through it in depth.

Psychiatrist's Guide to Conversation: https://www.youtube.com/watch?v=tIATzLf-y04