How would you describe the next 5 years of your life in a sentence?

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

How would you describe the next 5 years of your life in a sentence?

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

What do you want most out of life?

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 do you want most out of life?

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

When was the last time you tried something new?What makes you want to do better?

Look for your opportunities to ask this question:

When was the last time you tried something new?What makes you want to do better?

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

What are you most proud of?

Look for your opportunities to ask this question:

What are you most proud of?

Remember, the point is to learn more about the person and gain new insights as well as experience. Enjoy!