When bringing up money, there is a way to be inquisitive, yet not too overt.
"Frame questions as 'What if … '" Allison Kade, a millennial money expert with Fabric, told Business Insider. "This way, you can start understanding their underlying psychology by asking broader questions."
Some of her favorite examples include "If you won the lotto, what would you do with the money?" and "If you had to choose between working 90-hour weeks for the rest of your career but making a ton of money and working 20-hour weeks but scrimping, which would you choose, and why?"