Five Questions to Turn Chit Chat Into Friendship, Growth and Fun

If you’re like me, you meet a lot of people at professional events and in social settings. And you find yourself making small talk—asking (and being asked)—the same four or five questions: What do you do for a living, where are you from, where do you live, and tell me about your family or your education. If your conversation partner is particularly thoughtful, he might ask you about your personal interests or how you got started in your line of work.

It’s easy to see why many people dread this small talk—it’s often an inauthentic way people simply fill the time until the program begins, the event ends, or someone more interesting comes along.

I, on the other hand, have come to gladly anticipate this kind of chit chat. Instead of seeing it as an unpleasant and unavoidable part of professional or social events, for me, it’s a chance to begin to identify people who share common interests and perspectives and who might become lifelong friends. It’s also an opportunity to learn more about human nature and life in general.

A lot of that has to do with the questions I like to ask people I meet for the first time. What follows are five of my favorite questions. See if any of these are useful at your next social event.

  1. What’s your favorite thing about the work you do?

This question is such a natural transition from (or substitute for) “What do you do for a living?” If you’re going to learn about what a person does for work, you might as well learn about what he likes best about it. And this question can help you to quickly get a sense of how enthusiastic or optimistic a person is by how easily he calls to mind the things he likes about the work he does.

  1. What’s your least favorite part of the work you do?

I like this question more for what it reveals about a person’s outlook than for the specific answers it yields. Is this person a complainer? Does he despise his terrible boss, horrible coworkers or clueless clients? You can learn a lot about a person’s disposition and character by the way he answers this question.

And, as a bonus, I guarantee that if you ask enough people this question, you will discover that things you do are the greatest source of irritation for them in their line of work.

  1. What are you currently reading?

I love this question because it can help to quickly discover a person’s interests, and for the obvious reason that it’s a way to find great books to read. A revealing follow-up question is, “Why did you choose to read that book?” And if you want to know what’s helped shape someone into the person they are today, try asking, “What books have had the greatest impact on your life?”

These questions confirm for me that few things have the power to impact the quality of your life like the people you surround yourself with and the books you read.

  1. What are you excited about right now?

This question can seem a bit strange, which is why I usually don’t open with it. Sometimes I think adults think they aren’t allowed to get excited about things. However, when you do get someone talking about things she’s excited about—an upcoming trip, a recent purchase, a promotion or graduation, or a hobby, collection or side project she’s passionate about—it’s such a great way to get to know her.

  1. What are your biggest challenges?

I like this question because it can reveal ways you can be of service to someone. Perhaps you have a skill or ability that could help someone solve a problem she’s facing, or maybe you know someone who does. And sometimes this question can help you to learn from other people’s experiences and avoid pitfalls that might otherwise trip you up.

Remember, successful people ask better questions. That’s as true in social settings and everyday interactions as it is in our major life decisions. If you haven’t already, think beforehand about the questions you ask people when you meet them. Then, view what you previously saw as meaningless chit chat as an opportunity to make new friends, learn something useful, and enjoy yourself. And help others to do the same.