You know exactly what I mean.  You are at an orientation, a conference, a coffee shop.  You’ve met someone who seems interesting and interested in talking.  What’s one of the first questions?  “What do you do for a living?”  My favorite most smarty pants response I’ve ever received is, “I live full time for a living.”  Cue first HINT that there might be better questions to ask someone you truly want to get to know.

I didn’t like that the first inquiry in “normal” exchanges was essentially, “What do you do to be able to pay your rent?”  Really, when you think about the question that is what you are asking. I will offer some of my favorites…with this caveat.  I often step outside the lines of expectation with a gentle warning.  I say “I know it’s normal to ask what you do for a living, but I’d rather ask you…

“What makes you feel keenly alive?”

“Do you have a pursuit or hobby that really enlivens you?”

“Does what you wanted to be when you were a kid have anything to do with what you do professionally now? (This one comes the closest to finding out what they actually do when they “punch the clock.”)

“How do you enjoy spending your leisure time?”

“If you could spend all your days doing absolutely anything you wanted, with no concern about financial obligations – what would an ordinary day look like?”

These questions yield me greater insight into a new acquaintance.  They also serve as a compatibility litmus.  Any person that finds these questions utterly foreign to their experience – will likely find me utterly foreign.  Questions like this are one of the key explanations why I stopped receiving invitations to casual cocktail parties!  So, be warned. If you are fond of casual meaningless exchanges, do not pull these questions out of your conversational briefcase.

If you were to create a set of alternative questions – what would some of yours be?  And are you willing to give one or two of them a ride in your day and see where they might take you?  Let me know.