Ask HN: How do I get better at questioning?

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.

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!

A few thoughts;

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.

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.

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.

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...

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.