1, #81 - Questions to skip small talk

Estimated Read Time: 38 seconds.

Photo by Gil Ribeiro

I recently found out that two of my favorite modern storytellers use the same question(s) to draw out an interesting story, even from strangers.

Brandon Stanton (creator of Humans of New York) likes to ask:

“How has your life turned out differently than you expected it to?”

And public radio legend Ira Glass does almost the exact same thing:

“How did you think the situation was going to work out before it happened? And then how did it really work out?”

These questions are a natural setup for a story because they define a clear beginning and a clear end, and invite the other person to reflect on what happened in between. What better way to get to know someone than exploring the tension between their expectations and their reality?

Certainly better than asking “Where do you work,” or talking about the weather.

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Insight inspired by

Polina Pompliano

, who made this point and shared both quotes in this delightful article: 10 Interview Techniques From the World’s Best Interviewers.