Want to be the most captivating person in the room (virtual or actual)? It doesn’t matter if you’re an outgoing butterfly or introverted wallflower. You have the smarts and charm to be interesting in conversations. Memorable and stimulating dialogue can lead to fruitful connections down the road. Awkward small talk, on the other hand, makes you cringe and seek out the quickest escape.

What makes for interesting conversation? It all starts with a question. The next time you initiate an exchange, stay away from ho-hummers like, “What do you do for a living?” or “How about that weather, huh?” Set a more memorable tone with one of the questions below. Of course, some of these inquiries require a less personal, more general introduction, but don’t linger on the usual, boring topics.

One more thing: Don’t ask a question you’re not able or willing to answer yourself!

What’s your story?

If I’ve already built enough rapport with someone, I sometimes ask an alternative version: “So, what’s your deal?” Asking someone to share their story with you is not only flattering to them, but it also can lead to an anecdote that might stick with you for years.

Maybe your interlocutor flew one-way to Tokyo after graduating college 25 years ago because she wanted to learn Japanese. Perhaps you’re talking to someone who’s just three states shy of bicycling across each state in the continental U.S. Such stories stay with you for a long time.

How do you know (host of party/mixer/event)?

Asking this question is one of the easiest ways to find common ground with the other person, especially if you haven’t talked before. People who discover a mutual interest tend to build more rapport with each other. If nothing else, the question might result in a riveting tale.

What book are you reading right now?

Assuming you’re talking to someone who reads the occasional book, this question can reveal quite a bit about the other person’s personality. For example, there’s a correlation between loving classic literature and having a good deal of empathy. The book they discuss might also tell you about what impacts them, and it can spawn intriguing follow-up questions.

A caveat: Far too many people say they don’t read or have the time. Read the room. If you’re at a casual party with a bunch of people you don’t know, you might steer clear of this question. If you’re at a professional networking mixer, then it’s totally appropriate. By the way, when I’m interviewing or a job, I always have the title of a book to discuss in case I get this question.

What’s been the best part of your day (week)?

I can’t think of a better way to start a conversation on a positive note. Give your interlocutor a chance to brag a bit. If they happened to earn a promotion or get an article published that day, they might be itching to tell someone. Hearing about their own accomplishments might uncover a commonality between you two.

Tell me about a defining moment in your life.

This is another great question for building quick rapport and inviting deeper sharing. Their answer will probably reveal something significant about their personality or worldview. If nothing else, it could start a reciprocal exchange of captivating stories. You probably need to open with one or two casual questions before diving into this one, especially if you’re chatting with a perfect stranger.

What’s the best compliment you’ve ever received?

You never know when a single compliment can have an incredible impact on a person’s life. A compliment that someone clings to can reveal how they see themselves. It’s also refreshing to hear how the person appreciates the impact someone else had on them. If you expect to interact with this person again, it’s nice to know what boosts their mood.

If you could have picked your own name, what would it be?

I’m not sure asking someone what they’d rename themselves is that deep or thought-provoking. But it can make for a lively conversation. To be smooth, start with something like, “Hey, I always like asking people this . . .” For the record, I love my name, Juliann (pronounced “Julie-Ann”). However, gun to my head, if I had to pick a new first name, it would be Julia.

Why did you choose your profession?

This is a much better alternative to the snoozer, “What do you do?” If this question is your icebreaker, make sure you follow up and ask them to talk more about their choice. A career path might reveal a person’s motivations, what they’re enthusiastic about, or how they define themselves.

It’s possible that your conversational partner isn’t happy in their work. They might open up about what they’d rather be doing and why. What if you had a tiny part in getting someone to think about and act on a much-needed career change? Cool, huh? There are a couple of people I can credit for mine.

What’s the best restaurant you’ve been to?

A variation might be, “Is there a good restaurant you’d recommend around here?” Whether you’re a local or out-of-towner, this question could guide you to a great new hangout. Of course, a favorite restaurant also hints at a person’s likes, tastes, or lifestyle. Keep exploring this topic and you both might discover more common interests.

Final Thoughts

Sure, being a great conversationalist starts with a question, but it’s much more than that. It all boils down to showing genuine interest in another person. Whether or not you initiate the conversation, keep a few of these questions in your arsenal. Asking a question that puts the spotlight on someone else is not just a nice thing to do; it’ll make you a more interesting person.

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