Notes on Questioning

Unformatted checklist of meta-questions

Owing to a curious mix of mostly my own reluctance to question and the archaic educational system (with the former being predominant), I felt lost in asking questions and navigating unknown things. Ultimately circumstances force me to answer blatantly avoided questions, and my mental state in such scenarios is far from poised and peaceful. Somewhere along the line this has shifted, and now “asking questions” is one of the top skills I want to excel in.
Books are a prominent way for me gather information around a topic (in this case, questions). These are just my notes from “A More Beautiful Question” by Warren Berger. I use this as a checklist of questions/tips to go through from time to time, to sharpen the proverbial axe, and as raw material for self-reflection.

Selling point

  • power of inquiry - Van Philips and his newly designed prosthetic limb
  • Questions are engines of intellect - converts curiosity to controlled enquiry
  • asking questions is what separates us from primates
  • We live in a world of questions we create.
  • With the increasing amount of information around us, it’s as if we are going back to our childhood days, having to ask why at each turn.
  • Because of tech and knowledge availability, if you like questioning, it’s a great time to be alive.
  • More questions => more raw material to work with.

Oppositions to questions:

  • questioning often has a reverse relationship to expertise
  • Diffusion of responsibility - “Someone else will solve it”
  • Education system hasn’t evolved, still relying on having the right answers, rather than the right questions. Society has become entrepreneurial, educational system has remained industrial.
  • when you have asked a good question, it feels like it’s your job to get the answers.
  • Questions are often seen as something that holds us back.
  • If you ask a question (say when challenging some status quo), it doesn’t mean you need to have an alternative ready.
  • Prototyping is not an easy strategy given the way we’ve been schooled - wherein a project had to perfect and ready before being presented - you always had to show the final thing.


  • Questioning well and effectively, as opposed to just be willing to question - open questions (what? how? why?) are often better than yes-or-no type closed questions.
  • Questioning as a way to zero down on the most important items.
  • Problem finding: Searching for a problem
  • The 3 stages: Why/What if/How
  • Often the worse thing you can do with a difficult question is to answer it quickly.
  • “How” involved prototyping.
    Fail forward!
    How stage is where the actions take off.
  • Not enough to question endlessly – Zero-in on what you’ll like to work on.
  • Did you ask a good question today?
  • Sequential inquiry process can be triggered by a catalytic question - Why can’t we have the photos sooner? - Polaroid
  • Having a healthy enough ego to be the lone questioner in the room.
  • To ask “why” we often need to stop doing, stop knowing.
  • Being comfortable with not knowing - What do I do not know?
  • One can train oneself to have a child-like inquiry ability.
  • Broadening or narrowing the question:
    Why is this person difficult to get along with? => Is this person difficult to get along with?
    Questions can carry assumptions. It’s necessary to challenge them too - Meta-questioning.
  • Contextual inquiry: Getting closer to a problem to ask a better question.
  • The difference between asking a question or pursuing it is the difference between flirting with an idea or living with it.
  • You often need to “live“ with the question, rather than just ask it.
  • When working on a difficult problem, put aside some time to review all the challenges and questions. Then “sleep on it“
  • Creativity stretching exercise: Mix two different ideas to produce outrageous ideas - Stirs the mind.
    Vampire Hunter - Abraham Lincoln + Vampire hunting.
  • prototyping (or hacking) is an embodied question, a manifested initial version of an idea. Once it’s there, it becomes harder to ignore it.
  • Beware of being stuck in “What if” for too long. There’s no substitute for quick prototyping and learning from mistakes.
  • It’s a dynamic environment, we need to be good questioners, and good experimenters.
  • Experimenting is an approach that is laced with failures. Programming often constitutes hypothesis and test style of work. The key is not to get discouraged. To move from one failure to the next - What went wrong here? What went right here? Am I failing differently each time?
  • Dissonance (“that would never work”) is the most underrated and misunderstood kind of feedback. It means we’re entering uncharted territory. It’s more valuable that resonance.
  • Drawing insights and experiences of other people - Different people tend to get stuck at different places. Diversity fuels creativity.
  • Sharing a question is akin to challenging someone - many curious minded people will find it hard to ignore it.

Personal questions:

  • Figuring out what you want is a continual search. Questions are a means to the search.
  • What makes you tick?
  • Why am I climbing this mountain in the first place?
  • Are you evading inquiry? Why?
  • Is there some aspect of your life which you feel is determined, fixed?
  • Sooner or later, you’ll face the challenging questions - so why not get into the habit of asking them sooner?
  • People who are good at questioning are uncomfortable with uncertainty.
  • “Butterflies in the stomach” might be uncomfortable when asking tough questions.
    But soon it should become a welcome sign that you’ve charted into an interesting uncharted territory.
  • Questioning should be done as a matter of habit and process - otherwise, it’s not likely to find a place in busy schedules.
  • Step back, before you lean in - Take some time to gather clarity before jumping in on an endeavour - It might need to step away from the noise to a “tortoise enclosure“
  • Appreciative inquiry - What am i grateful for? The tendency is to look for things to improve. Can we take out some deliberate time and think of things going well in our lives.
  • What is important to you?
  • What did I love doing as a child? Will it still work for me?
  • What would an optimistic, confident person do?
  • What is one small thing which can have a great impact?
  • What is the one thing which you would like to stop doing?
  • What would you attempt if you knew you would not fail?
  • Categorise failure better - avoid failure fetish.
    How do I distinguish between an acceptable failure and unacceptable one?
    How do I see failure - end state or temporary stage in the process?
  • When embarking on a new endeavour - What if I fail — How will I recover?
    If the project involves risk, envision what would happen if you failed? What would be needed to pick up the pieces?
  • What’s truly worth doing, whether you fail or succeed?
  • Picking a project/endeavour is similar to climbing a mountain — You start of by picking the mountain and make sure you actually want to do it, not just one you would like to be on top of — because most likely you’ll be stuck on it for years.
  • How do I stay inspired?
  • What if we learned to cultivate and navigate ignorance, rather than fearing it?