12 questions to turn small talk into real talk 

So much of getting to know someone is about asking the right questions (and really listening to the answer). If you’re feeling stumped on how to get beyond weather, kids, and menu options, use these prompts to guide you towards stuff that really matters. I’ve separated them into three categories to help you identify which questions to ask depending on situation and individual:hello

  • Passion – For individuals you admire and want to model your own life after; figure out what gets someone going, what moves them, brightens their day, fuels their dreams, inspires their work.
  • Personal – For individuals you’d like to get to know better; these questions can be effective ice breakers to better understand motivations of an acquaintance.
  • Bridge – For individuals you’d like to collaborate and partner with; these questions allow you to assess areas of overlap and uncover how you can thoughtfully connect and add value.


Uncover the sources from which individuals draw inspiration to learn more about their interests and gain added reserves of creativity, insight, and spark for yourself. See how they view the world (and think about ways you might help).

1. What inspires you?

2. What one problem do you presently wish you could solve?

3. If you were given 1 million dollars, what would you do with it?

4. What’s your favorite aspect of your work?


Not everyone finds it easy to talk about their hobbies, dislikes, and passions. Concrete questions can facilitate discussion and provide insight into someone’s dreams and goals. Ensure conversation feels less like an interview and more like an exchange by offering complementary ideas when appropriate.

5. What does your perfect day look like?

6. What would “your book” be about?

7. What do you wish you would have learned in school (but didn’t)?

8. What are you afraid of?


Identifying pain points and similar areas of interest can assist your effectiveness as a connector and impresario. Turn an introductory conversation into something worthwhile by leaving something valuable behind — a new idea, a business contact, an unavoidable question.

9. What’s the most difficult part of your work?

10. What has been the most valuable introduction you’ve received?

11. Where are you stuck?

12. How can I help?