Tag Archive | Questioning


Fragment from imaginary dialogues

“What’s the best answer?”

What’s 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) time-line 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 time-line, 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.

On Implementation 2

The question you should be asking isn’t, “What do I want?” or “What are my goals?” but “What would excite me?” (Tim Ferriss, The 4-Hour Workweek)

Fragments from imaginary dialogues

“How can I implement this wisdom?”

“Here’s a few ideas.

Use the question as a filter.

Whenever you look at a set of options, ask yourself:

What would excite me?

Order the options based on how exciting they are; eliminate the unexciting ones.

Expand the question.

For instance, you can use it in the context of Self-Awareness.

Ask yourself about the activity you’re engaged in,

How exciting is this?

You always have two choices:
change the activity to a more exciting one (selective)
make the activity (more) exciting (creative)

As concerns the latter, ask yourself:

How can I make this exciting?

How can I beautify this?

How can I play with this?
How can I make it fun?

You can also use it in the context of habit creation.

Remember James Clear’s four rules.”

“Make it obvious. (Cue)
Make it attractive. (Craving)
Make it easy. (Response)
Make it satisfying. (Reward)”

“You can upgrade the third one to,

Make it exciting.

Which brings us back to,

How can I make this exciting?”

Two Games

When force of circumstance upsets your equanimity, lose no time in recovering your self-control, and do not remain out of tune longer than you can help. Habitual recurrence to the harmony will increase your mastery of it. (Marcus Aurelius)

Fragments from imaginary dialogues

“Even if I no longer play it, Magic the Gathering remains one of my all-time favorite games.”

“What do you like about it?”

“The art of it, the creativity, the design, the structure, the modularity, the variety, the flavor, many things.

Magic is really not one game but a series of different games connected by a shared rule set and game pieces. (Mark Rosewater, head designer for Magic)

For me, Magic is a beautiful resource, a rich metaphoric system, a source of design inspiration, and in many ways, a model for The Beautiful Game [<link; medium length].

Magic the Puzzling

The picture you see is a Magic the Gathering puzzle, a game situation specifically created by someone to solve.

However, I like to see any game situation in Magic as a puzzle.

You have a set of game resources (life total, cards* in your deck, cards in hand, cards on the table), and a unique game state, and you have a limited time to make the best possible decision given these circumstances.

I realize, for me, part of the joy of playing Magic was solving such puzzles, and adapting to any game situation.

In the same way, any life situation can be seen as a beautiful puzzle to solve.

You have set of life resources (energy level, learned mental tools, mental tools available, prior set-up/build-up), and a unique life state, and you have a limited time to make the best possible decision given these circumstances.

We could call this The Decision-making Game. Its essence can be captured with a question:

What’s the best decision?

However, unlike Magic, the Decision-making Life-Game has an additional layer: accessing your resources, which is dependent on your mental state.

In an unresourceful state you only see problems not solutions. (Tim Ferris)

Being able to play the Decision-making game requires that you put yourself in a resourceful state. Or, to use Tony Robbins’ (and my preferred) terminology, a beautiful state [<link; medium].

We can think of being in an unresourceful state as being out of balance.”

“Makes me think of what Brian Johnson called ‘The Equanimity Game‘ seeing how fast you can recover balance once lost.”

“I love Brian’s idea of The Equanimity Game. This is just my take on it.

Whenever you’re out of balance, the micro-quest (and absolute priority) becomes to recover it and to return to the beautiful state.

“What if you made the beautiful state your baseline, your center?”

“That’s one of the life-puzzles I’m working on right now.

The Equanimity Game and the Decision-making Game are twin games. The Equanimity Game is an enabler, it sets the stage and opens the door for the Decision-making Game.”

* The cards in Magic the Gathering represent spells, and mana-generating lands that allow you to cast the spells.

Beautiful Tools: The Oracle

The purpose of querying an oracle is not so much to foretell the future as to enable the questioner to delve more deeply into his own intuition when dealing with a problem.

Most oracles contain a series of messages from which the questioner randomly selects.

The oracle is intentionally ambiguous in order to force you to go beyond the first right answer.

Random insights can force you to look at your problems in a way you would not have otherwise.

(Roger von Oech, Expect the Unexpected (or You Won’t Find It))

Fragments from imaginary dialogues

“How can I get better at asking questions?”

Consult an oracle.

“Are you being an oracle right now?”

“Yes, and no.

Yes because my answer can indeed serve as an oracle if left ambiguous.
No because I’m going to disambiguate it.

The oracle is a beautiful creativity tool I know from Roger von Oech’s wonderful book Expect the Unexpected (or You Won’t Find It). The book, which is about using Heraclitus’s epigrams as an oracle, opened my mind to the beauty and usefulness of ambiguity.

I am a Models Thinker [<link; medium read], so I turned the Oracle into a mental model.

As you know, I love randomness [<link; read] as a design tool, and I implemented my own random quotes system [<link; read] on my phone.

Quite recently, an idea struck me:

What if I implemented an oracle in my random quotes system?

Which I did.

Using the paired-quotes system, I set the one on top to a selection of beautiful questions related to some practical puzzles I’m working on solving, and the one at the bottom – the oracle – to my entire quotes collection.

The question changes every four hours.
The oracle every 5 minutes.

The result is beautiful. Every time I check my phone, I get a little dose of creative joy, in the sphere of the practical, like this one:

The Oracle

On reading and change

Learning is behavior change. Eben Pagan

Fragments from imaginary dialogues

“The books you read change you.”

“Do they?”

“Well, can change you.”

“Big difference.

Whenever you make a statement, make it a habit to turn it into a question as well.

Do the books you read change you?”

“I guess it depends on the books.”

What you read is indeed important. It’s important to be selective about books. 
How you read is equally important.

The ‘quality over quantity’ principle applies to both the what and the how.

It does depend on the books; but mostly depends on you.”

“But there are books that can change you regardless of the how.”

“Some books can change you on a representational level, by reshaping your mental model/map of reality.

Some books can change you on a pragmatic level, if you apply what you learn.”

The Art of Asking Questions 2

Fragments from imaginary dialogues

“Why do you think he did it?”

“I think it’s because x.”

“Are you certain of it?”

“Not really. Maybe it’s be because y, or z.
Why do you think he did it?”

“I don’t know.

I think an important aspect of Questioning (The Art of Asking Questions) is knowing what questions to ask, and when, and what questions are worth answering.

In this case, the energy expended on generating answers was wasted. We simply don’t have enough information.”

“What would have been some better questions to ask?”

“Without insight into the context of someone’s life, the probability of error is very high, almost a guarantee.

Sometimes it’s not a matter of what question to ask, but whom to ask. Sometimes no one can know better than the person in question. And sometimes not even they know.

The idea is to approach it from a position of humility: I don’t know.

One possible question to ask is:

Is generating possible answers in this case likely to get me closer to the truth?

Sometimes it does, sometimes it doesn’t.

Another useful approach is generating answers through the filter of Empathy, Compassion, and our common humanity.

There’s a quote I love:

Be kind. Everyone you meet is fighting a hard battle.

Everybody hurts, everybody struggles. Even if you’re not likely to get closer to the truth of the matter, you get to practice Empathy and Compassion.”

Childish questions

Fragments from imaginary dialogues

“You ask such childish questions.”

And what do adultish questions look like?