Recently, I’ve realized I’m not as good at asking questions as I’d like to be. By that, I mean asking questions to better understand something, think critically, extend a conversation, spark creativity, deepen relationships, etc.<p>I feel like I've lost that child-like curiosity that drives kids to ask questions incessantly. I don't want to emulate the "Why?" rabbit-hole that kids do, but I do want to rediscover how to ask more thoughtful and meaningful questions. I don't feel like I have the "question-vocabulary" to come up with them.<p>Any advice or resources (books/podcasts) would be helpful.
If you’re into it I suggest you try some pen and paper role playing. I’ve done various forms of communication courses on bachelor level as part of transitioning into management. Part of this is role playing and so on. I’ve done various HR workshops and I’ve read books on the subject and so on.<p>Nothing I’ve done has come close to improving my ability to ask questions compared to playing adnd 2e (because I’m old). Dungeon master is obviously where it’s best, but you’ll pick up a lot of tricks from experienced GMs even if you’re a noob player. It’ll also be one of the few places you’ll learn to communicate with a variety of people you typically won’t meet.
Well the damn irony of it; that's the best question I've seen on Ask
HN this year!<p>A few thoughts;<p>Courage. Most people hate questions and they recoil, punishing whoever
dare ask. Keep up your confidence in asking the things you know people
don't want to think about - while not being a provocative dick for the
sake of it.<p>Scepticism is a skill, if simply the skill of not falling down the
hole of cynicism. Study Socrates, Erasmus, Sextus. Cicero, Hume, etc,
but also moderns like James Randi, the fictional detective Columbo
(Peter Falk), and great interviewers like Wallace, Frost, Walden, and
even Louis Theroux Sacha Baron Cohen. The hardest questions are asked
softly.<p>Study "epistemology" and scientific method, so you know what "truth"
looks like if you occasionally encounter it. Most of everything is
bullshit and is constructed of parochialisms, psychological biases,
hidden alliances or simply people's jobs depending on them thinking
and saying certain things. Be comfortable with ambiguity and not
getting satisfactory answers.<p>If you are asking questions constructively with a goal or problem in
mind there's a great book by Polya called "How to solve it" that
demonstrates the methods of constructive enquiry - understand the
problem, make a plan, decide what counts as evidence, ask the
questions, review your experiments, improve your method...<p>Be fallible. Don't get overly attached to ideas, knowledge or
positions. And have fun... being curious and sceptical makes for a
lifetime of motivation and seeing the world afresh.