What to Say (Conversational Skills, Part 3)

Last week, I covered some of the conversational pitfalls to avoid. But what makes a *good* conversationalist? Being a good conversationalist is about doing most of the conversational work. This does not mean doing most of the talking. In fact, it can mean doing less of the talking than the other person.

One aspect of conversational work involves coming up with questions that make people feel interesting. Yes, I said interesting, not interested. People will love to talk to you if the questions you ask make them feel they are interesting. Such questions help people put forward their best, funniest selves. And people, self-centered bastards that we are, tend to like people because of how we feel about ourselves when we are around them. If I like who I am when I’m with you, I’m going to want to spend more time with you.

We’ve already established what these questions are not. They are not vague questions like “What have you been up to lately?” It takes no thought, no real interest in the other person to ask “What’s new?” You could ask that generalized question of anyone. And it makes your conversational partner do the work of coming up with a topic of conversation. An interesting question has more specificity. This may mean knowing and remembering things about people in order to ask questions tailored to them. It may mean thinking of a topic you’re interested in and asking the other person their opinion (rather than spouting your own viewpoint right off). An interesting question elicits conversational meat. You’ve got yourself some conversational meat when you are able to elicit someone’s opinion or strong feelings of excitement or passion. (Eliciting strong feelings of annoyance, anger or fear should be avoided.)

If you don’t know the person at all your first question may have to be a boring one, like “Where did you grow up?” The key is the follow-up question. Instead of saying “I hear it’s hot there” or “I’ve never been there,” ask:

“How is the culture different here than where you’re from?” Or if the person is from the place you currently are, ask “How is it different today than when you were little?” These questions will get you into the realm of opinion and people’s likes and dislikes. People love sharing their opinions about the crappy drivers in the city they’re living in now.

Another question that will lead you into the realm of opinion is “Did you hear about (a political issue, movie news, video on YouTube, etc.)? What did you think of it?”

Another potentially dull initial question you may find yourself asking someone you don’t know is the typical “What do you do?” On the one hand, this question shows your interest in the person, her background and an activity to which she devotes a large portion of her time. On the other hand, understand that most people’s jobs, let’s face it, are boring--either to the person who has to do it for a living or to you or to both of you. Even if the job seems interesting, really, the day to day of it is boring--even being a film actor is mostly boring. But your follow-up question does not have to be. You do not need to ask for details about what she does--unless you really care (or she seems really excited about her job). Instead ask “Is that what you went to school for?” Most people chose their college major because they were fascinated by the topic, so regardless of whether it matches their current job or not, you now know a topic that they’re passionate about. If you are interested in the day to day of what she does, it’s best to ask her a technical question that she can give advice on. Most people don’t want to list what they do all day or explain exactly what their job is--it feels too much like having to justify getting a paycheck. If you ask her advice, it makes the other person feel important and lets her display her knowledge and therefore feel good about herself.

Up on Friday: more on the art of conversation.