Questions for Strangers

Meeting a stranger is a once-in-a-lifetime moment. So, we must give it its due. Serendipity may have brought us a friend, a customer, a partner, a mentor, or something we cannot comprehend yet. Time will do the rest, but if you find yourself in this fortunate situation, here are a few questions to consider asking.

1. What's the most interesting thing about your life so far?

This establishes you as someone who cares.

2. What do you want to learn next?

What we choose or care to learn about tells a lot about what matters to us.

3. If you could be anywhere right now, where would you be?

Home isn't always where the heart is. Sometimes you leave it behind on your travels.

4. In a room full of people you love, who would you hug first?

A choice, even one made in abundance, always becomes a test.

5. If you could meet anyone you wanted to whom would you choose? What would you ask them?

Will they stay in this period or inhabit the future or past? Our choices make us.

6. If you could teach me one thing, what would it be?

This shows you are here to listen and hopefully learn from them.

7. What's your superpower?

We're all superheroes but do they know what's their gift yet?

8. What do you think people love and hate about you?

Perception vs. Self-Realization. Subjectivity vs. Objectivity.

9. What's been your biggest failure till now?

Failures are the corpses of our dreams. And if or when we learn lessons from them, we build monuments.

10. What has someone said to you that will stick with you forever?

What we choose to keep is what matters to us.

11. Hard: Are you happy?

If they answer it in a binary, then dig deeper. Happiness never comes in a single shade.

12. Hard: How do or will you measure your life?

OKRs and KPIs exist for everything. But this is when it really matters.

13. Hard: What's something that others value that you don't?

This will tell if they have the courage to be disliked for being different. What we disregard speaks volumes about what we hold dear.

This thought was inspired by Ankit Kumar.  Thanks to Varun Shetty and Rasha Kutty for reviewing drafts of this.