The world can be scary. Strangers can be unpredictable. And some people still believe there's a clear line between personal and professional. So it's pretty understandable if somebody you know keeps a wall up between themselves and you. The best collaboration and innovation, however, comes when team members see each other for who they really are.

If you really want to break through someone's shell in a kind way, hit them with questions that encourage authenticity like those below.

  1. What's your opinion on...?
  2. What's on your mind today?
  3. Where/How did you learn that?
  4. What would you do next?
  5. Can you explain your rationale?
  6. What does that mean for you?
  7. Which people do you admire or look up to?
  8. What's the best way for me to help you?
  9. Are you comfortable/feeling OK?
  10. Is X working/enjoyable for you?
  11. What's your main goal?
  12. What makes you laugh?
  13. What do you like to wear most or feel most comfortable in?
  14. What do you like to do on your free time?
  15. What is your favorite part about...?
  16. What would you change?
  17. What motivates you?
  18. Have you ever...?
  19. What has your experience been with...?
  20. What do you know about...?
  21. What's the biggest value to you?
  22. Would you mind sharing...?
  23. Is there anything else you think is important?
  24. What else should I know?
  25. What would you do if...
  26. What do you think is the best way to...?
  27. What is most convenient for you?
  28. What are your expectations?
  29. What's your preference?

As you quickly review this list, you'll notice that all the questions are all open-ended. They dive into a person's history, likes and dislikes, personality and values, and they all give the impression that their individuality is of interest and consequence. They're also questions that allow you to continue the conversation with personal information of your own. That kind of sharing can help the other person relax and serves as a demonstration that openness is perfectly OK.

Lastly, remember that having the right question is only the start. How you ask it is just as important. Avoid a frantic pace or tone, and mirror the other person's body language. It can be helpful to ask these questions one-on-one rather than in front of a group, as well. A little at a time, you'll ask your way to impenetrable trust.