Skip to content

⁉️ 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.

Further References