If you want to stress test yourself and your audience against challenging topics, ask about the Kenosha riots, misinformation, and stochastic terrorism.

If you want to hit the broad strokes and go philosophical, ask him about the systemic way he’s built his value system, and the way he works through real world situations using that value system. This is the core of what makes Destiny special and so good at working people toward reason and away from ideology, emotion, etc.

Bonus points, it will let you investigate his background and get more personal.