Getting Off Conversational Auto-Pilot

I haven't kept track but I'm guessing conversation has been one of my most popular blog subjects to date. I'm usually social and more extrovert than introvert so I suppose this isn't surprising. 

Many of us think we're good at conversation, just as we think we have a good sense of humor. I'll suspend judgment on both of those common self-assessments, but I have been reflecting lately on the effort I put into recounting anecdotes I think will amuse others. That led me to wonder: How much richer would my conversations be if I put equal effort into recalling information about the people with whom I'm conversing? What if I concentrated as hard on what the other person just said to me as I do when trying to be clever or make a pun? It struck me that I'm often willing to work at being funny, while perhaps taking other important conversational skills for granted. In other words, aside from the funny bit, I'm on auto-pilot a lot.

How about you? How hard do you work at keeping your conversational saw sharp? How much do you let any wish you have to be amusing get in your way?