20 Questions Only Interesting People Ask During Conversations


5 min read
Interesting Conversations

See if you recognize this scenario: You walk into a networking event or social function and the first extroverted person drops the suspect questions we’ve all heard ad nauseam: What do you do? Where are you from?

Predictable and exhausting. As you run through the scripted answer in your head, you wonder, “Is this is someone I really want to talk to?”

The problem is most of us are guilty of asking those dreaded, superficial questions that lead nowhere beyond the small talk.

The key to creating meaningful interactions? Take your eyes off of yourself and place it on the other person. By giving them the attention first, you’ll have a clear edge: People are naturally wired and looking for connection and positive affirmation – to be seen and heard. And it all starts with asking the right questions. So kill the small talk and ban questions like “What do you do?” and “Where are you from?” in favor of these great conversational starters.

What’s your story?

Your Story

This open-ended question is bound to trigger something interesting after the other person gets over the initial shock that you asked it. By opening up a conversation in this manner, you’ve given them access to speak from their hearts and share their life’s journeys, dreams, and goals.

What makes you smile when you get up in the morning?

A great question that gets the interaction hopping on a positive note from the get-go. Watch the other person’s wheels turn as she reflects on something for which she’s excited or deeply grateful.

What is that one book that has influenced you the most?

The brilliance behind this question is not the question itself, but the invitation for follow-up questions because of the book’s impact on that person’s life, marriage, career, or business. Asking it deepens the conversation (and the connection) as you learn more about how the topic has positively altered that person’s life in some way. If they’re not avid readers, ask about movies or famous people.

What absolutely excites you right now?

Exciting Conversation

This question triggers passion. Who doesn’t like to speak from their most passionate space? It may end up being their thriving career, a new job, or an exciting new phase of their business. It could be personal: the arrival of a new baby, having beaten cancer or finding true love. Whatever it is, think of all the places the conversation will lead, and the possibilities of connecting the dots with the other person when it’s your turn to shine.

What’s the most important thing I should know about you?

In line with all the others, this question will elicit emotions to deepen the conversation and find connecting points. That’s what you’re after – creating space to discover what makes the other person tick, unique, or maybe frustrated so you can offer encouragement or make a difference in his or her life.

What movie or book character do you most identify with?

This is a question where people can explain their inner workings and have fun with it at the same time, especially if the character is someone from a slapstick comedy movie.

When are you happiest?

Happiest Conversations

The beauty of questions like this is that they skip all the surface stuff and go right to the heart. It gives the person the opportunity to be personal and meaningful.

What more are you wanting from your career right now?

People at networking events are predisposed to be thinking about career questions, and this is much more meaningful than “where do you work” or “what do you do.”

If you were to start a company from scratch, what would be its core values?

If the person you are speaking with is an entrepreneur, the answer will be what was the mindset when the business was started. It gives both of you a chance to connect on shared values.

What stresses you out the most at work?

No matter how much you love what you do, there are things that stress you out during the workday. Being able to talk about them is quite therapeutic.

If you were to go to jail, what would it be for?

This one is a little edgy, but the answers could be enlightening and fun. You could hear something like, “Embezzlement – I’d relieve Warren Buffet of a couple billion dollars so I could rebuild that distressed neighborhood across town.”

If you could learn the date and time of your death, would you?

Date Time

This is one of those great philosophical questions that is a yes-or-no question but could have an infinite number of reasons behind it.

What’s the most embarrassing thing you’ve ever done?

This will definitely lower any defense walls, especially after both people have given an answer.

Have you ever shoplifted? If yes, what did you take?

Most people who say yes will likely include “when I was a kid…” Or so we hope.

What are the three things you would bring with you to a deserted island?

Desserted Island

This is a fun question that will identify what is most important to a person.

Who was your most influential schoolteacher and why?

The answer gives insight into how a person’s values were formed.

What would be the title of your autobiography?

The answer to this question should certainly bring some fun answers.

Do you have a favorite season?

Favorite Season

It’s a little on the “small-talk” side of things, but should bring a variety of answers. You can find out what makes someone tick with questions like this.

What’s the fanciest event you’ve ever been to?

If you are asking this question at a particularly fancy event, you might get “this one” as an answer. If you’re at a more casual event, there might be a greater variety of answers.

If you could go back to one historical event to witness it, what would it be and why?

You should also get a wide variety of answers with this question.

Finally, did you notice a pattern?

It should be obvious. Here’s a hint: You take the initiative and make the conversation about the other person. People love to talk about themselves. This selfless act of putting the spotlight on someone else makes you the most interesting person in the room.

Now you are equipped to handle that next gathering with new people that will make it a very enjoyable experience.