Questions on questions

Questions to grow, connect, catalyze, and get out of the box.

Asking good questions is the key to this small thing… relationships with another beings. Pretty much, there’s “people just telling you stuff” and then there’s you asking questions. That’s how we connect to, relate to, and exchange things with others.

So, in the dry land of questions discourse, I created this resource for myself to always have a meaningful question at hand for meetings, parties, and one-on-ones. They’re sorted by frequency—so at the top, you’ll find the ones I find most useful or universally applicable. I often forget a text within a week of writing it—so you’ll probably forget this one within an hour of reading it. But you can save this easy URL pawel.world/q now to never have a conversation depleted of fun or meaning again.

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Relationship with X

• What’s your relationship with X?

There is a colossal difference between the answers to “How is your fitness?” and “What is your relationship with fitness?”. Try it and then ask about almost anything “What is your relationship with food? With the internet? What is the history of your relationship with music? With travel? With leadership? With taking responsibility? Strength? Vulnerability? Fashion? Self-expression? Optimism? Being a public figure? Privacy? Intimacy? via Visa in Friendly Ambitious Nerd

Surprise about X

• What most surprised you in X?

Maybe my favorite question ever—and I use it to ask about anything. But then people are often like: “Nothing!”. But wait… there’s always some delta between your expectations and reality, yo. And then people start sharing the most interesting takes on their trip, book, or someone they met. And learning to notice surprise is such a great muscle to train—a real world-opener, world-discerner.)

If you die

• If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why? #19 from The 36 Questions to connect

• If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet? #33 from The 36 Questions to connect

Rose

I use this framing very often when catching up with friends. Something about the rose makes it memorable. Why rose? Petal = best part, thorn = worst part, bud = growth. via Nasimeh friend.

• What was a moment of joy?

• What broke your heart?

• How did you grow?

Questions for self inquiry

Use these questions to journal about your life, or to guide conversations or deepen your understanding of others. Below is a set from Speaking for the dead, a book sparked by the need to be in truth when talking about our lives. The author wrote it because he grew dissatisfied with how funerals distort the lives of the dead—telling stories so far from who they really were, effectively making them even more dead. So he invented the Speaker for the dead: someone who would investigate the life of a dead person and give a speech “with full candor, hiding no faults and pretending no virtues.” This, in turn, had an untangling effect—not just for the memory of the person, but for the entire communities.

• Who the person really was?

• What their life really meant?

• What they wanted to do — what they actually did?

• What they regretted — what they rejoiced in?

Askhole

Askhole is an amazing question card game co-created by Aella. Here are my fav ones.

• Have you been loved enough?

• Have you ever had (what you consider to be) a spiritual experience? If so, what was it like and what effects did it have on you?

• What unusual trait do you find most attractive in a romantic partner?

• In what ways do you tend to fail at communication?

• Of all the beliefs you hold, which is most likely to be considered barbaric in 150 years?

• If you could have one but not the other, would you rather love someone or be loved by someone?

• If you could press a button that would instantly erase every single false belief you have, would you do it?

The 36 Questions to connect

If I could, I’d rename *The 36 Questions That Lead to Love to* 36 Questions to Connect—to drop the one-directional agenda. A few of the questions aren’t great, but as a set, it works—and there are definitely some great ones in there. It’s a solid framework for getting to know someone, not just in romantic settings. This set helped popularize question sets and holds a solid spot in the history of questions discourse. A few questions I like:

• If you could change anything about the way you were raised, what would it be?

• Take four minutes and tell your partner your life story in as much detail as possible.

• How close and warm is your family? Do you feel your childhood was happier than most other people’s?

Questions to destroy a relationship

How direct do you want to be when asking questions? How far do you want to tread? My low-confidence, low-committal guess is: as far as the question renders judgment. Duncan Sabien created the following set that makes you ponder this. In his own words “in the spirit of the classic 36 Questions to Fall In Love “here are some high variance, negative expectation value questions to answer with your loved one.” Here are a few questions that may, with the right attitude, help grow within a relationship.

• #11 Imagine your partner could change to be much more like the kind of person they wanted to be. Are there ways in which you think they would become worse from doing this?

• #12 To what extent does your partner's success make your relationship better or worse?

• #6 If your partner was dating someone else and that person broke up with them, what would you guess was the reason why?

• #14 What true statement has the maximum probability of causing you to break up right now?

To unlock agency

Questions to unlock agency can work surprisingly well…

• if i had 10x the agency i have what would i do?

Nick Cammarata: “i hate how well asking myself `if i had 10x the agency i have what would i do` works. just an immediate list of solutions to like half the problems in my life appearing out of the ether. if i had more agency i'd ask myself about 100x but i'm too scared to see what it produces”.

Tyler Alterman also has a group of agency unlocking questions. Fav ones:

• What would you work on if you had no fear?

• Describe your ideal day. what you do, what your environment looks like, who are you interacting with. anything you imagine. it doesn’t have to be grounded in any of your present circumstances

Top-idea in your mind

“What is the top-idea in your mind?” is a great question from Paul Graham's essay. But I think people often feel put on the spot when asked what’s your “top” anything. Here are some fun reframes that get at a similar idea:

• What is under-valued or under-discussed?

• What does your mind naturally gravitate toward exploring?

• What should I start thinking more about or doing more of?

Other brainy questions:

• What did you recently change your mind on?

• What should be thought at schools that currently isn’t?

There are a few people who maintain great content–question pages—here are some: Patrick Collison, Alexey Guzey, Gwern

Question on questions

And finally, a meta-question:

• What are your favorite questions?

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And pointing this back at you—what are your favorite questions (or sets of questions)? Which of the above feel most useful or alive to you? What did I miss? How do you like to ask—in ways that actually build connection, help you understand better, or get you out of the box?