5 Questions the Most Interesting People Ask to Spark Great Conversations

Whether you’re an introvert, extrovert, or ambivert, it doesn’t really matter. To truly captivate people in a conversation requires the right approach to keep them engaged.

Most of us don’t have a good internal barometer for knowing when we bore others, since we think we’re so fascinating. Truth is, curiosity is the secret weapon for having great conversations and increasing your influence

Several studies agree that curious people connect better, cope better with rejection, and enjoy socializing more. In fact, other people are more easily attracted to and feel socially closer to individuals that display curiosity.

Curiosity drives interest on both sides of the conversational table. But you hold the key to initiating it by being genuinely interested in what the other person thinks, what makes him or her ‘tick,’ and how he or she views the world.  People with curiosity (and humility) understand that they don’t have all the answers and that each person they meet, and each experience, has something to teach them.

5 questions to ask

That brings us to the questions that set the foundation for great conversations. A typical scenario looks like this: You meet someone for the first time and strike up a conversation. The next thing out of your mouth may be:

• How are you?
• What do you do?
• Where are you from?

Instead of asking the casual, basic stuff we’re all tired of answering, you want to hit ’em up with great conversational questions, beginning with my No.1 most favorite question:

1. What’s your story?

I start every podcast episode by asking my guests this very question. It’s disarming, open-ended, and usually triggers an intriguing story about the other person’s journey — the pursuit of a compelling purpose, a defining moment in someone’s life, or a special talent.

Granted, this and the other questions listed below may require you first to begin the interaction with more mundane questions to build rapport and put the other person at ease. So, use your best judgment. If you already know the person is open to discourse and willing to jump right in, go for it. And it goes without saying: Return serve by answering these same questions yourself.

2. What would you say has been a defining moment in your life?

This is another great question that invites the other person to share on a deeper level, which builds momentum and rapport quicker. As stated previously, you may need a few casual questions before this one to help set the mood for hearing about a profound moment or transition in that person’s life.

3. What (or who) did you dream about being when you were growing up?

Asking this is a great way to introspectively draw out a unique story from someone. We all dreamed about being something growing up–a doctor, a police officer, an astronaut, a superhero, and so on. Connect the dots to the present by asking if the other person still has those same aspirations as an adult (including being a superhero!).

4. If you could know the absolute truth about something (an event, a person, etc.), what would it be?

Ever wonder who really killed JFK? Is the moon landing a hoax? Is there a God? Whatever the answer–serious, cerebral, funny, or ridiculous–it’s interesting enough to clue you in to the other person’s interests, values, beliefs, or sense of humor.

5. Why did you choose your line of work?

This is one of those questions I call “peeling the conversational onion.” Learning about how people landed in their given profession has layers. It’ll tell you what defines them, what motivates them, what they’re passionate about, and whether their work is their calling or purpose. It may also trigger a different, more thought-provoking response: Some people aren’t happy in their jobs. By asking, you may be in the position to assist or mentor a person through a career or job transition (or hire someone on the spot for your own company).

Did you notice a refreshing pattern in these questions? It’s you who takes the initiative and makes the conversation about the other person. People love to talk about themselves–if they have something worth talking about that adds value to the conversation. Once they know you’re safe, by asking first, they’ll appreciate your showing interest. This selfless act of putting the spotlight on someone else makes you the more interesting person in the room.