If money was no issues how would you spend your time?

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

If money was no issues how would you spend your time?

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

What was your childhood dream?

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

What was your childhood dream?

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

What is something new you tried recently and loved?

There are lots of things that you don't know about people. Here's a question that may help you learn more about someone:
What is something new you tried recently and loved?

Make notes about how people react to the question as well as what their answer is. Good luck!

Who are your heroes?

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

Who are your heroes?

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