How to know someone quickly? Ask for his choices.
In a macro level, you couldn't see the real differences (in a short time).
Ordinary people share common values in healthy, honesty, discipline, ...
So don't ask for his goals, they mean nothing.
Losers have golas, winners have systems.
You have to judge him by his systems, his patterns of how to make choices.
Only then, how he works for these choices matters.
They should be HARD rather than just REALISTIC.
For examples, the famous 36 questions
to fall in love with anyone in 45 minutes, most of them are IMAGINARY choices:
- Given the choice of anyone in the world, who would you want as a dinner guest?
- If you could wake up tomorrow having gained one quality or ability, what would it be?
- What, if anything, is too serious to be joked about?
Also, Tim's “rapid-fire questions” in 2 to 5 minutes:
- What is the book (or books) you’ve given most as a gift?
- What topic would you speak about if you were asked to give a TED talk on something outside of your main area of expertise?
- Do you have a quote you live your life by or think of often?
Ask questions about his choices, and observe his systems.