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August 20, 2020

Eight Questions That Go Deeper Than Small Talk

“Small talk” refers to polite and surface-level conversation that often occurs at the beginning of an interaction with someone, especially with someone you’ve just met. Although it can feel artificial or forced, I believe it’s a necessary starting point for creating connection and rapport.

But, how do you get beyond small talk and move more quickly into deeper discussion? One way is to utilize powerful questions that encourage an engaged and authentic exchange.

Before offering some of my favorite powerful questions, here are a few caveats: First, know that asking these questions will take a bit of courage and confidence. Due to their atypical nature, they may surprise people at first. Secondly, keep in mind that you can’t force someone to engage in deeper conversation if they’re not open to it. Finally, be prepared to answer these same questions yourself. Good conversation is reciprocal!


Here are eight questions that go deeper than small talk:

What do you enjoy most about your work? or What’s most challenging about your work? These two questions are a good follow-up to the typical introductory question of “So what do you do for a living?” They elicit deeper responses since people usually have a lot to say about what either excites or frustrates them.

What are you passionate about? This is a pretty broad question, but that’s a good thing. It leaves people open to talk about a wide variety of topics, such as personal hobbies, family members, work, or a cause they care about.

What was your biggest childhood dream? This question can encourage a little storytelling, and likely some humor. It can also help someone reconnect with interests or passions they’ve abandoned in light of the more “practical” considerations of life.

What do you hope to be doing in a few years? This question prompts discussion of the future. Through the resulting conversation, you may be able to help someone create new clarity or renewed motivation around their goals or vision.

What’s a favorite memory you have of the last year? This question involves reflecting on the past.  Based on the answer, you can learn a lot about what someone values in life, whether that’s relationships, professional successes, volunteer work, personal interests, or travel.

What’s something you’ve read or listened to lately that inspired you? This is an easy question to ask and answer since so many of us consume content all the time, either from books, blogs, or podcasts (like the Skybound Leadership Podcast :).

If you could have any super power, what would it be and why? This question is fun, playful, and good for breaking the ice. It also feels particularly resonant these days considering the multitude of superhero movies and products currently dominating pop culture.

What’s a movie you can watch over and over and not get tired of? I find that most people have a few of these type movies, and are usually excited to talk about them. These are the films that have struck a particularly resonant chord in some way, either because of their nostalgia, compelling storytelling, comedic factor, or inspirational characters. Because movies tend to inspire and stir-up emotions, they’re things people can talk about pretty easily. This subject can also tell you something about a person’s values, interests, and personality.

Happy conversating!

For more tips, see my 11 Steps to More Powerful Networking, 12 Networking No No’s, and 8 Keys to Mastering the Personal Pitch.

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