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⁉️ Asking Better Questions

Let's start this week with a short list:

  1. The most simple, seemingly silly questions are almost always the most profound.
  2. Good questions must come from a sincere desire to learn, rather than as a veiled means of stating your own opinion.
  3. Experts rarely ask good questions. Be a beginner, always.
  4. Questions are an opportunity to be humbled. Asking good questions is indistinguishable from practicing humility.
  5. Own up to what you don't know. It will set others free and you may end up coming closer to the shared truths which are a hallmark of honest conversation between peers.
  6. Close listening and clear attention are preconditions for good questions.
  7. A real master is the pupil in the eye of the world. Don't be afraid of letting others teach you; it does not degrade you, it uplifts you. The ego doesn't always acknowledge this simple truth.

Asking better questions is about process and practice. It's something you need to work on consciously. It is a skill, not an innate personality trait and it can be developed in much the same way that you can become better at coding, or cooking, or gardening.

This goes to the heart of the thinking methodology we're advocating here. If you're able to identify patterns of meaning by considering the complementary opposites implied by any idea you are presented with, you will naturally ask better, simpler, and more direct questions.

The starting point is to ask yourself, "What does this really mean?" It's not about "How can I use this?" or "Why is everyone else excited?" It's about whether you can understand the basic principles. If you can't, it's either because it's not a well-formed idea (in which case, move on!) or because you need to learn a new skill in order to understand its implications. Which implies, again, that you need to be willing to learn if you are to practice the art of asking better questions.

How do you develop a willingness to learn? It begins with clarity and honesty about what you don't know. As soon as you stop hiding behind all the ego's pretenses and claims to knowledge, you will realise how little each of us actually knows. Such honesty automatically makes you more incentivized to improve yourself, because no-one likes feeling inept (even though we all are).

In so doing, you can begin to experience the benefits of beginner's mind yourself, not conceptually, but in the actual course of your life. Beginner's mind is about starting now, trying for yourself, being frustrated by your lack of expertise, and letting your heart show your mind how to celebrate this fecund state of not-knowing - for therein lies both truth and liberation.

68 Life Lessons

Questioning "Better" Questions

Corey Petty and Justin B question the claim made in point 3 above. The debate boils down to whether asking good questions in general is an ability best developed through disciplined exercise of rational skill, or the cultivation of "beginner's mind". In particular, techniques like the Socratic Method develop rational inquiry in order to fuel deeper, more intuitive understanding of a given topic. Corey writes:

Experience and reflection, learning from our mistakes, and developing understanding all provide nuance. A mechanic doesn't develop his ability to diagnose a problem solely from introspection. It is through the combination of knowledge and understanding that intuition arises. I've spent most of my life honing skills that give me broad and deep understanding for the specific purpose of being able to ask good questions in any context.

Or Justin B:

I feel that knowledge of the specific, e.g. computer science, translates directly into intuition around the general.

The mechanic or scientist's skill does grow more nuanced through acquisition of knowledge and skill by the exercise of discipline, and this does lead to more specific questions about utility. In this way, honing a skill makes you good at asking questions about that particular discipline, which is a good thing. So, let us add an 8th point:

  • Asking good questions requires a deep appreciation of context.

However, "beginner's mind" is not opposed to rational inquiry and the honing of skill: it is, in fact, the pinnacle of such discipline. Consider the Socratic method more closely:

Socratic Circles are based upon the interaction of peers. The focus is to explore multiple perspectives on a given issue or topic. The pedagogy of Socratic questions is open-ended, focusing on broad, general ideas rather than specific, factual information. The technique emphasizes a level of questioning and thinking where there is no single right answer.

Rational inquiry demands a diagnosis; a solution; and end to a process which had its beginning in the mind. What can such a mind do in the face of "no single right answer"? It can develop negative capability, but even this is insufficient, because we're not after skillful intellectual understanding: we seek harmonious and clear ways of living. To achieve this, rational inquiry must not be denied, but taken to its own end in order to see, not that it does not currently know, but that it cannot know in principle. Honest acceptance of the limitation of mind is the most effective method for cultivating the humble emptiness necessary for genuine curiosity and an interest which asks from the heart, and so goes to the heart of the subject being questioned. It is, as Paul Myburgh says, perceptual rather than conceptual: simple knowledge of things-as-they-are, not our own complex understanding.