Question Optimization

Fragments from imaginary dialogues

“Can you express this with fewer words?”

“Always ask yourself two meta-questions:

Can you ask a better question?
Can you ask this question better?

I call this process, question optimization.

Let’s optimize your initial question.

Can you express this with fewer words?
Can you express this with fewest words?
How can you express this with fewest words?
How to express this with fewest words?

How to express this briefest? (Brevity principle)

I call this a short-form question. Everything but what’s essential was stripped away.”

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The most important meta-question

Fragments from imaginary dialogues

“What is the most important meta-question [<link; short read]?”

“What is the most important question you can ask in any moment?”

“What is the Macro / Biggest Picture / highest-order level?“

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.”