Tag Archive | Questioning

The Art of Asking Questions 4

Fragments from imaginary dialogues

“How do you deliberately practice questioning?”

“I have a system for it. I’ve even created my own terminology.

The system has several components:

  • QuestionCollecting (QCollecting)
  • QuestionGeneration (QGeneration)
  • QuestionEvaluation (QEvaluation)
  • QuestionOptimization [<link; very short read] (QOptimization)
  • QuestionTemplating [<link; medium read] (QTemplating)

QCollecting is exactly what it sounds like. I collect questions to use as tools and to learn from them. Key to this process is collecting not only good questions but also bad ones – they help you identify error patterns.

QGeneration and QEvaluation are complementary practices.

QGeneration is the practice of generating multiple alternative questions. One component of it is a practice I call QStorming [<link; short read], which is essentially BrainStorming with questions. You start with a central point of focus (QFocus), which can be a theme or a problem you’re trying to solve, and you generate questions based on that focus.

QEvaluation is the practice of narrowing down the generated questions to discover the best ones. Another aspect of it is a practice I call QAnalysis: deconstructing questions with the purpose of learning from them.

QOptimization is the practice of optimizing questions. Taking a bad question and turning it into a good question. Taking a good question and turning it into an optimal question – or set of questions.

QTemplating is the practice of turning repeated question patterns (QPatterns) into question templates (QTemplates). This means, whenever you notice multiple questions with the same structure, keeping the fixed part of the questions and replacing the changing part with variables:

How can you optimize Learning?
How can you optimize Writing?
How can you optimize x? (QTemplate)

What ties everything together is a practice I call Meta-Questioning: the process of asking questions about asking questions – I call this type of questions Meta-Questions [<link; short read] (MQ).

Can you ask a better question? (MQ)
Can you ask a bigger question? (MQ)
Can you ask a x question? (MQTemplate)
Can you ask this question better? (MQ)


On remembering what’s essential

Fragments from imaginary dialogues

“There are moments when I can’t remember what’s essential.”

“Temporary forgetting is inevitable. You can hold nothing in mind indefinitely. So be prepared for it.

Have a ritual for reminding yourself of what’s essential.

“What do you have in mind?”

“I’m thinking journaling/questioning

Take a piece of paper and ask yourself questions:

What’s essential?

What’s important?
What’s important now?
What’s the most important thing?

What’s the priority?

I’m also thinking reading

Read from a selection [<link] of the most powerful ideas you know that remind you of what’s essential. As you know, reading a couple of them one after another has an emotional flooding [<link; short read] effect.”

The Art of Perception 12

Any particular way of looking at things is only one among many other possible ways. (Edward de Bono)

Fragments from imaginary dialogues

“We have the tendency to stick with the first interpretation that comes to mind. We often forget – some can’t even envision – that things can be interpreted in multiple ways.

The interpretation triggers emotion, which leads to further interpretation, which maintains and often amplifies the emotion.

Interpretation => Emotion => Interpretation => Emotion

The initial interpretation acts as an anchor on which we base all subsequent interpretations.”

“What is the initial interpretation based upon?”

“Past experiences, sometimes from the very distant past.

Your past subtly influences your future. Unless you break out of such patterns, your past is your future.”

“What’s the practice?”

Remember always that objective reality is neutral. We project our subjective reality on it through our interpretations. 

Always question your first interpretation. 

Generate multiple alternative interpretations, and select the most beautiful one.

Pattern-Breaking Questions

Fragments from imaginary dialogues

I lost balance.

“How is this beautiful?

I call this type of question, pattern-breaking questions.

Expressed as a template:

How is this x?

How is this fun?
How is this funny?
How is this a gift?


Fragments from imaginary dialogues

“What are meta-questions?”

“Meta-questions are questions about questioning (the art of asking questions), used to become a better questioner.”

“Can you give some examples?”

“Here’s a few:

How can you deliberately practice questioning?

Is this question useful?

What is the essence of this question?

Can you ask a more beautiful question?
Can you ask a better question?
Can you ask a bigger question? (Big Thinking)
Can you ask a clearer question? (Clarity)
Can you ask a more specific question? (Specificity)

How can you optimize this question? (Question Optimization)

What is the optimal sequence for asking these questions? (Sequencing)

What is the Most Important Question? (Josh Waitzkin)

What is the biggest question you can ask? (Big Thinking)
What is the most energizing question you can ask?
What is the most powerful question you can ask?

Is this question open or closed?
How can you turn it into an open question?

“How do you come up with them?”

“I have a document titled meta-questions. Whenever I think of one, I add it to the document.”

Question of the Day

Fragments from imaginary dialogues

“Being part of a Facebook group called Daily Questions (That Will Make You 1% Smarter) inspired me to create a similar system for myself. I call it QD – Question of the Day.”

“What does it look like?”

“As you know, I collect questions [<link; short read]. To be more specific, I collect beautiful questions, by which I mean the 20% most powerful/interesting questions I find.

The essence of the system is creating a selection of beautiful questions, and extracting one at random every day.

I use my phone for that. It looks like this:

Question of the Day

“Still using your random-quotes system [<link; medium read]?” 

“It’s imperfect, but I haven’t been able to find anything better.

I dream of replacing it with the CommonBook [<link; long read] someday.”


Fragments from imaginary dialogues

“Which career path should I take?”

“Start with BrainStorming (BStorming).

What are your perceived options?

You can do it with mind-mapping. Write ‘Career’ in the middle of the page, and branch out in all directions.

Continue with QuestionStorming [link; medium length] (QStorming).

You can do it using two pages – one for mind-mapping, and one for questions.”

“Why not just one for questions?”

“The essence of any question can be captured in a few words – it’s essentially a model. You can reverse-engineer the process by starting with the models, and using it to generate questions.

Something like this:

As you come up with a relevant model, add it to the mind-map.

Using the map, start generating questions.

It might look something like this:

Which option is the most meaningful?
Which is the most aligned with your purpose?
Which is the most aligned with your highest aspirations?

Which does your gut guide you toward?
Which makes you feel most expansive?

Which is the most exciting?

Which offers the most growth potential?

Which can you learn most from?
Which has the highest learning-density potential?

Which allows you to develop future-proof skills?
Which allows you to develop transferable skills?

Which would you most like to do if you weren’t afraid?
Which is the least comfortable?
Which is farthest outside your comfort zone?

Which is the most painful in the short-term?
Which is the most painful in the long-term?
Which is the most pleasurable in the short-term?
Which is the most pleasurable in the long-term?

Which offers the highest potential ROI (Return On Investment)?
Which has the highest life-stacking potential?

Which would Future-You be most grateful for?

You get the point.

And you can invert all of them – to practice Inversion [link; medium].”

Project Question-Templates

Fragments from imaginary dialogues

“I LOVE questions.

I want to master Questioning (The Art of Asking Questions).”

“What’s your approach?”

“I practice it constantly. I have a special notebook only for questions. 

Another thing I like to do is deconstruct questions. One outcome of this is the creation of question-templates [<link; medium length], which are a practical tool for generating questions. 

One of my latest projects is gathering all the question-templates in one place.”

“How do you organize them?”

“I have a document for each of the question-kernels:


Their structure looks like this (x, y, z are variables):

What x ?

What x now?
What [do you want to focus on] now?

What x next?
What [do you want to focus on] next?

What x y ?
What [beautiful opportunities] [are there around you]?
What [problem] [are you trying to solve]?
What [book] [do you want to implement next]?

What are x ?

What are [the answers]?

What are the fundamentals of x ?
What are the fundamentals of [Learning]?

What are the [superlative] x ?
What are the [most powerful] [resources you have]?

What can x ?

What can you x ?
What can you [add]?
What can you [subtract]?
What can you [play with]?

What can you x y ?
What can you [play with] [in this context]?
What can you [practice] [now]?

What do x ?

What do you want to x ?
What do you want to [feel]?

What do you want to x y ?
What do you want to [master] [in the next ten years]?
What do you want to [master] [in this lifetime]?

What does x ?

What does x y ?
What does [a quality rep] [look like]?
What does [a quality rep] [feel like]?

What if x ?

What if you eliminated x from y?
What if you eliminated [activity z] from [your life]?

What is x ?

What is [the answer]? (One Thing)

What is [essential]?
What is [exciting]?
What is [the next step]?

What is your x ?
What is your [compass]?

What is [superlative] x ?
What is the [most powerful] [resource you have]?

What makes x ?

What makes [you come alive]?

What makes x y?
What makes x [fun]?
What makes x [funny]?

What might x ?

What might [this look like from their perspective]?

This is but a very small glimpse of it.

As a mind-map it looks like this:


Fragment from imaginary dialogues

“What is the best answer?”

What is the best question?

“How can I discover the best question?”

“I use a technique which I call QuestionStorming, or QStorming for short.

It’s like BrainStorming, but with questions instead of ideas.”

“What’s the process?”

“You start by writing down the problem you’re trying to solve. This will be your focus point throughout the process.

The process is simple: 
– Generate as many questions as possible.
– When you reach a previously established threshold (eg you fill up a page, or a certain amount of time has passed), start organizing, evaluating, optimizing, and engaging with the questions.”

“Can you give an example?”

“Yesterday the day went beautifully at the beginning, but then it started going downhill. At the end, I did a QStorming session.

It looked like this:

How do you feel?
How do you want to feel?
What’s positive about this?

What’s the best response?
How would the Sage respond?

How can you use this to get stronger?
How can you use this to evolve?

How can you turn this obstacle upside down? (Inversion)
How can you transcend this obstacle?

How can you make this effortless?

What can you learn from this? 
What’s the
gem? (Principles)
How could you have done it differently?
What were the failure-points?
What were the decision-points?

What (skills/values) can you practice?

Seeing the problem as a system, what are its elements?

What variables are the most relevant?
What contextual-variables are the most relevant?

“Which yielded the best practical insight?”

“It was a synthesis of more than one question.

I drew a (vertical) timeline with all the failure points and the decision points, and listed all relevant contextual variables, to get a big-picture view.

Then I started analyzing the timeline, paying attention to patterns, making notes of what I could have done better at every step.

I finalized the process by listing the principles.

I ended up calling this process retrospective analysis.”


Fragments from imaginary dialogues

What is templating?

Templating is the practical use of templates. You’re familiar with the template in computer-use.

You mean the preset formats for documents and such?

Yes. That’s but one application of it.

In essence, the template as a model is a structure with two components: one fixed and one variable.

Can you give some examples?


You can use templating to create an optimal structure for the day (day template). The fixed part of the template is the part of the day you have most control over: the beginning and end of the day. Someone called them the AM and PM Bookends. And you can go granular. You can have templates for the bookends themselves (AM/PM templates) and for your working hours as well (deep-work template).

You can use templating with movement (movement templates). You can have a fixed part of a few selected movements, and play with building on and around them.

To optimize any activity, you can turn it into a template.

You can also use templating with language (linguistic templates).

My favorite linguistic template has to do with questions (question templates).

For instance let’s take the question,

How can you optimize Optimization ?

We can transform it into a template by identifying the variable part:

How can you optimize z ? (Template)

z‘ here is a variable. You could replace it with… well, anything.

How can you optimize Learning ?
How can you optimize Conversation ?
How can you optimize Questioning ?

And we can further deconstruct the question:

How can you y ? (Template)

‘y’ here is another variable.

How can you beautify z ? (Template)
How can you play with z ? (Template)
How can you turn z into creative inspiration ? (Template)

The furthest deconstruction level is:

How x ? (Fundamental Template)

This is the most basic question template. I call it a question kernel.

I presume the other question kernels are:

Why x ?
What x
Where x ?
When x ?”

Indeed. These are the fundamental seeds from which the Art of Asking Questions (Questioning) grows.