Prompt by tinacyr, image by Midjourney.

How to ask good questions?

The biggest misunderstanding when it comes to asking good questions? We think we need to *start* with them. That’s rarely the case. Good questions are discovered, unearthed through observation. We have to work for them / root them out.

Most of us are not looking for good questions, we are looking for good answers .. this is a roadblock.

Because when we are looking for answers we make judgements, jump to conclusions, interpret what we are learning through what we already know (biasing what we are learning).

In his book ‘Look’ Christian Madsbjerg talks about the act of observation. And how hard it is to hold off on judgement, assumptions and predictions until you have taken the time to properly observe. Madsbjerg points out how we are magnetic to making immediate judgements hampering our capacity for discovering something new.

It’s a study of experiences. It’s not what people think; it’s how. It’s an observation, not an opinion. — Christian Madsbjerg, Look

People who are good at asking questions aren’t looking for answers, they are looking for insights, understanding, empathy (empathy as in seeing the world through the eyes of the subject you are trying to understand).

If you want answers, go ask your LLM, if you want to get better at asking questions get to work.

In the words of Dave Snowden when someone was complaining that LLM’s couldn’t do mind maps yet: the entire point of the mind map is the thinking that goes into it.

Questions are hard work. They demand extra effort to be discovered and they will challenge you once you get them. Make sure you are ready for it!

These are four of my own tips from years of discovering questions / looking for the music in the noise / finding unknown unknows and being surprised:

1. Train yourself to avoid jumping to conclusions. Observe, observe, observe.
2. Be curious, let yourself be captivated by the subject. Let them / it lead you down their path, not your own.
3. Be brave and ask even the dumbest questions. We build our understanding in layers, if you are making assumptions about the bottom (dumbest) layer you might get every other layer (most likely there is always something more to learn about the bottom / dumbest layer).
4. Don’t lead with ‘why?’. This question demands no effort and will too easily only lead to the answers you want.

Further reading:

(1). Christian Madsbjerg, Look, https://www.penguinrandomhouse.com/books/712956/look-by-christian-madsbjerg/