Great Conversation

“There is nothing that makes me happier than sitting around the dinner table and talking until the candles are burned down.”  ― Madeleine L'Engle, A Circle of Quiet 

I used to say that nothing makes me happier than a good, meaty conversation. 

As the years have gone by, though, I have felt less and less able to pull my own weight in conversation. 

I run out of things to say or ask the other person about. Maybe I'm just not interesting enough? Have I stopped reading, learning, and growing, so I have nothing to bring to the table?

Whatever it is, when I'm on the spot, I often can't think of a way to take the talk from "small talk" to at least "medium talk," if that's a thing.  

Part of the problem may be that the conversations that dash my hopes are often one on one. The ideal number of people for a discussion that is simultaneously relaxed and stimulating, I propose (or at least prefer), is four. In a group of three to five, no one need carry the conversational ball alone, yet there's space for everyone to have their say. My new team at work is a team of four, and that feels just right.

Do you have any strategies for stimulating great conversations? What works for you?