What did you learn from your biggest regret?

A good question can lead to a lot of learning. Here's one for you:

What did you learn from your biggest regret?

Don't be surprised if you get some strange responses to this one. Ask well!

What risk are you happy that you took?

People, even shy people, love to talk about themselves. Here's a question that may help you open someone up:

What risk are you happy that you took?

Be sure and use active listening techniques as people answer. You'll learn much more that way!

What is one of the kindest things someone has ever done for you?

People, even shy people, love to talk about themselves. Here's a question that may help you open someone up:

What is one of the kindest things someone has ever done for you?

Don't be surprised if you get some strange responses to this one. Ask well!

What can you do that you could not do a year ago?

Asking questions shows that you're interested in others. Here's one you might find useful:

What can you do that you could not do a year ago?

Hopefully this will spur some good conversations for you. Good luck!