I came across a great book called The Socratic Method by Ward Farnsworth, which was recommended by Rich Hickey in his talk Design in Practice.

It’s an amazing book, easily the best one I’ve read this year. The ideas in the book have helped me to connect many thoughts I had before on “questions”.

The Socratic method is a style of thought and a method of inquiry that involves asking questions to stimulate critical thinking and to uncover underlying assumptions. It’s not about definitively answering hard questions, but rather about asking and pursuing them in order to arrive at wisdom.

One change I made every morning this year is to change TODO items to questions. Instead of writing “Fix the issue of slow builds”, I write “Why the our build takes ages to finish?”

On the surface, it might look very subtle or maybe even jokingly funny (obviously we can’t change every TODO into questions as well like booking a dental appointment for my kids). But I found myself way more engaged to solve the problem than merely following the directions.

More importantly, it has me naturally asking more and more questions. So you could easily see the trajectory of the problem solving process. By the end of the day, you just somehow feel you’ve learned more than merely solving that one problem. Those questions linger in your mind way longer than the TODO list.

One known common technique we use in postmortems is Five Whys. Sometimes it feels intense (interrogative), but most of the time, everyone ended up with a more clear picture of the overall situation and concrete ways to prevent it in the future.

At the same time, asking questions couldn’t be more relevant in the age of LLMs/ChatGPT. I once shared with my colleagues that I think the era of “fearing to ask stupid questions is gone”. Thanks to ChatGPT, anyone can ask any questions anytime without worrying the embarrassment.

I certainly found myself asking many more questions this year thanks to ChatGPT. Partly because lots of questions I have are so customized or context specific which was very hard to search or even find the right audience to ask. So I just gave up asking it all together. But now I can just briefly layout the situation and the challenge, let the LLM handle the rest of clarification or refinement of the questions.

Yes we might ask many bad questions, but aren’t they better than no questions?

Every time you ask and answer good questions, your understanding gets a bit deeper. You better understand the other side and the weaknesses on your side. You see more complexity.

A question puts pressure on whoever receives it. If you ask questions of yourself, you are the recipient of the pressure. That’s good. Stating an opinion is roughly the opposite. It releases pressure. Pressure is uncomfortable, so most people think and talk in opinions.

• The Socratic Method

One quote I really like is “Fall in love with problem, not the solution.” (Oh, there’s even a book now)

So let’s “Fall in love with the questions, not the answers.”