Ask Better Questions

How to make mundane experiences memorable?

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The most interesting people I know share a knack for making mundane experiences memorable. This seems inconsequential, until you realize that this skill is why they’re interesting, not the other way around.

Growing up, I assumed that people became interesting by doing great big interesting things. There was probably some separate reality these people lived, unburdened by the daily tasks that prevented me from having the same experiences. One day I would become an interesting person, free to focus on important things, and delegating the rest.

Anyone can be interesting in an exotic situation. Can you be interesting in line at the grocery store? How about commuting to work?

I’ve learned that interesting people tend to make even boring situations interesting. Especially boring situations. They do this by asking better questions.

Better questions encourage answers that are not predictable. Asking better questions allows people to surprise you. If there was an alternative to small talk, this would be it.

Our brains are constantly making predictions about what’s going to happen next. This is why optical illusions work: they take advantage of a mismatch between what we expect to see and what we are seeing. When we hear or see something that doesn't match our predicted outcome, we take notice. The right kind of question will catch your attention in the same way that an optical illusion does.

3 of Our Favorite Optical Illusions and How They Trick Your Eyes ...

Asking better questions is rewarding. You likely already know the answer to “how’s it going”, so why bother asking in the first place? Why not ask something you genuinely want to know? And if you can’t think of anything that you’d like to know, at least give the other person a chance to surprise you.

Good questions are unusual, specific, and make the listener give you their full attention. If you need examples, I’ve gathered a few from one of my favorite writers, David Sedaris. The following examples are real questions that he has asked:

  • Do you like milkshakes? 

  • If you have extra stuffing at Thanksgiving, do you feed it to a dog? 

  • Are you afraid of large animals like horses and cows? 

  • Do you like shells and sand? 

  • Do you have any friends named Daniel? 

  • Do you know much about the moon? 

  • Have you ever eaten pizza with corn on it? 

  • Do you chew your food carefully? 

  • Do you ever eat with chopsticks? 

  • Have you ever counted your teeth? 

  • Do you wear jeans? 

Asking these questions will signal that you’re genuinely interested in the other person, rather than just exchanging pleasantries.

Next time you’re doing something mundane, try one of the questions above or come up with your own. If you land on something good, I want to hear it. Send me an email with the results, and I’ll share the best ones. The only rule: you should be surprised by what you learn.


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