Skip the small talk (part one)

I’ve been running an experiment where I ask people at least one of the following questions to understand their thinking and personality better. I feel like a lot of time is wasted on small talk and discussing work, so I encourage you to skip all of that and see what interesting conversations come out of these questions!

  • If you were going to be frozen tomorrow for a one-way 1000-year interstellar voyage, what would you most want to communicate (and to whom) before you leave?
  • What do you think you’re most likely to regret on your deathbed?
  • What do you miss most about your past that could be recreated today?
  • What’s the most important thing to remember daily that you haven’t been able to?
  • What help could you most use that you haven’t asked for?
  • What is your one piece of advice to everyone here?
  • What was the last thing you fell in love with?
  • When was the last time you felt unbounded optimism?
  • Who was the last person you felt inspired by?
  • What simple thing still blows your mind?
  • What sparked your curiosity in whatever you’re most curious about now?
  • What’s the most useful concept you have that doesn’t have a name?
  • What’s something you believe but can’t defend?
  • What taste do you have that most people don’t have, where does it come from, and how has it helped you?
  • What is your most radical belief?
  • Do you think it’s more important to follow the “written” rules or the “unwritten” rules? What is one unwritten rule that you’ve learned?
  • What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?
  • Which fictional character would be the most boring to meet in real life?
  • What’s the closest thing to real magic?
  • If you could know the absolute and total truth to one question, what question would you ask?
  • Which question can you ask to find out the most about a person?
  • What do you want your epitaph to be?
  • There are two types of people in this world. What are the two types?
  • What is something you are certain you’ll never experience?
  • Who is/was your most interesting friend?
  • What small gesture from a stranger made a big impact on you?
  • If you had a clock that would countdown to any one event of your choosing, what event would you want it to count down?
  • What are three of the most significant numbers in your life?
  • Which of your personality traits has been the most useful?
  • Imagine you have a closet full of robots at the ready. Which of your various obligations would you assign to a robot? Which tasks and activities would you keep to yourself, because you enjoy them too much to delegate them to even a robot who is better than you?
  • What is the best measurement of how an idea is absorbed into culture?
  • Do you think you’re undervalued as a person? If so, why?
  • Why are some people so addictive?
  • What color best describes your personality?

Part two will be up when I come up with new questions!


21 thoughts on “Skip the small talk (part one)

  1. Hi Lama, a great article indeed.

    I got a question for you: How do you overcome one of the main reasons small talk is used – namely that asking random people or strangers intimate questions right away is in many contexts considered rude?

    Some of these questions I would need many iterations of small talk before asking them. But I like them all and even more I like the general concept: Make more use of the time you got with people. Given they’re not offended, you both will get much more out of the conversation.

    My favorite: “What is the most significant thing you’ve changed your mind on in the last year? Why did you change your mind about it?”

    Such a question can be a primer for people to open up about beliefs or opinions that are highly contested (e.g. immigration, climate-change… bike-lanes) as the asked person knows she can’t be put into the bad- nor the good-person box, because she’s been both. It’s a conversational safe-space.


    1. Hi Alex!

      I don’t do this list with everyone that I meet, and the ones with whom I do use this list of questions, I can gauge pretty well which ones I should ask them. I’m really upfront with them about this list, and give them a judgement call on how intimate they want the question to be. More than anything, they’re meant to be interesting conversation starters. I’m really awkward at the whole small talk thing and can’t really discuss what I’m working on at the moment, so I’ve found this to be a great alternative.

      Hope this helps 🙂

      Liked by 1 person

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  3. Lama,

    Great list. Seeing your name, perhaps you also speak languages other than English. Have you done this with other languages? Or in English with people in other countries? What’s been the experience?


    1. Glad you liked it, Dave! I have not tried it in other languages, though someday I might in either Arabic or French 🙂

      I’ve tried it with a few multilingual friends/non-American friends, and their answers have been great!


  4. Lama,

    Thanks for the questions, they’re terrific! I’ve taken them as an exercise in self-knowledge and answering them myself has been fun and challenging.

    Please go for part two!


  5. 1) tell my parents that they’re the best parents ever
    2) i’ll probably regret not telling my parents the above statement frequently enough
    3) i miss the intimacy of living with friends and the time i had that i likely took for granted. I’m trying to correct for this by making significant efforts like flying to see people.

    I’m wondering about your opinion on the following:

    These are fantastic questions and I hope you don’t mind if I use them for basically the same purposes!! As much as I am more extroverted than introverted, I also find a hard time with small talk because I tend to get into deep subjects too fast for many folks. I usually can get people to open up but, at the same time, don’t think that they should be doing so, so I end up feeling kinda bad/like I wasted their time/anonymity of their personal lives/one of the total “amount” of times that they’ll ever share personal details.

    Does that last piece make sense to you?


    1. Feel free to use any of them! That’s why I shared them 🙂

      Not everyone is interested is answering questions about themselves, and that’s fine. I don’t really think you have to worry about wasting their time. If they don’t want to share something with you, it’ll be clear and you should back off. Reading people is a skill improved with time and effort.


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