The Art of Asking Questions

Not long ago, I organized a small gathering including three people who didn’t know each other.  Keeping the conversation ball in the air was exhausting; the three “strangers” did not engage with each other.  All roughly the same age, they made no effort to get to know each other or inquire about each other’s’ lives. 

Flabby Social Skills

If such a lack of interest had been an isolated observation on my part, I could have chalked it up to a variety of external factors. I do believe, however, the art of conversation, i.e. the art of asking questions, is a talent missing in today’s culture.  Perhaps too much time on social media (It’s-All-About-Me Media) has made our social skills flabby.  Or, perhaps taking an interest in someone’s life is considered old fashioned.

Be Curious

Being a good conversationalist has nothing to do with one’s knowledge, intellect or accomplishments.  Although telling interesting stories or jokes is a hallmark of a good entertainer, these skills are not needed to be skilled in making conversation. Whether you’re an introvert or an extrovert, engaging with others requires little more than curiosity.

Most people respond well to someone taking an interest in them. Here are a few probing questions to ask of strangers you meet at parties and gatherings:

1.     How long have you lived in _____________ ?

2.    How is your work going for you?

3.    What do most like about….?

When I know very little about others, I like to ask how they structure their time (without assuming employment). I find that because of my age, some younger adults don’t bother to inquire about my work, likely assuming I am retired.  Making assumptions about someone’s interests based on age, race, gender or any demographic is short-sighted, at best. 

Bridging the Divide

When you meet folks outside your normal social circle, there is no better way of finding common ground than asking questions. Our current political climate is so polarized that even making small talk with those “across the aisle” can feel strained.  In such cases, one has to be careful not to confuse asking with accusing.

On my less gracious days, I want to ask, “what were you thinking?”, when meeting someone whose political beliefs are to the right of mine.  Politics aside, I had a recent meeting with someone who questioned me in a way that felt like the inquisition.  Her intent was to get to know me, I’m certain, but the tone and the prying nature of the questions felt uncomfortable.

If your questioning comes from a curious and generous place, people you meet will feel honored that you took an interest, and you will be considered a great conversationalist without having said much at all.