How to ask better questions

This is a followup to my "Master Your Questioning Skills" post. There I gave some suggestions about how to ask better questions, but didn't engage with the topic directly.
Coming up with the questions is not difficult, once you get out of your default mode and give yourself the license to indulge in the questioning frame of mind. 
By calling these questions MAD questions, I gave myself the license/protection to go wild, uninhibited by traditional assumptions/constraints. This gave rise to reducing the bar, and approaching the topic with a beginner mind, as an outsider. This made it easier to ask more original questions. By detaching and discarding the baggage of tradition, you can start working from the first principles. 
To get to the good questions, get over with the bad questions. Bad questions lead to good questions. So roll with them and exhaust them to get to the good questions. 
A good question gives you a perspective change that is productive. It opens a new area to explore. It creates new relations/connections.

Then I asked: "Is it possible to teach how to ask great questions?"
Answers are teachable, so we teach answers. But we don't teach how to question. In kindergarten and primary school, the kids are already pretty good at questioning, but come middle school most kids stop asking questions. I don't know... Maybe students that ask questions come across hard to manage and contrarian, and get discouraged by teachers and adults. We (academicians) try to teach questioning during PhD by way of example via apprenticeships. I am not aware of any organized/formal way that asking better questions is being taught. There is no course or good book on it, as far as I can see.

Here I try again to provide one more method/approach that can enable asking better questions.

Of course, the best I can offer on this is my subjective experience. The premise here is that "I ask good questions". I think I do. And others also tell this about me. There is a chance I have an inflated view about my ability to ask questions, but I think I am above the average. (Dunning Kruger effect, I know.)

Anyways, here is my working theory about how I got better at asking questions. This is because... I always have working theories about everything. Sometimes these are analogies about "how this one thing looks somewhat like this other thing". Often these are just educated guesses based on the models of world I have in mind.

I have working theories about everything because I constantly try to make sense of things in advance, with the limited information available to me. Some of these working theories are contradictory with each other, yet I am OK with keeping them clustered together in my mind, and living with them for a long time. I came to be OK with carrying conflicting and incomplete theories about everything. I never fully believe any of my theories. Sometimes I find myself defending both sides of a debate to the surprise of my students. One of my PhD students once told me: "But you once said this about this topic", and I told him, "I say a lot of things, don't take me too seriously." I think the cardinal sin is being too certain about anything.

As I cultivate these theories, I tend to keep refining them and cut out the incorrect models. I naturally want to test which ones are closer to the truth. So I come up with questions to test them. These questions turn out to be deeper questions that cut to the heart of the matter.

These theories help immensely because, as the book "Range" explains:
Struggling to generate an answer on your own, even a wrong one, enhances subsequent learning. Socrates was apparently on to something when he forced pupils to generate answers rather than bestowing them. It requires the learner to intentionally sacrifice current performance for future benefit.

Metcalfe and colleagues have repeatedly demonstrated a “hypercorrection effect.” The more confident a learner is of their wrong answer, the better the information sticks when they subsequently learn the right answer. Tolerating big mistakes can create the best learning opportunities.

I think my mom was influential for me to cultivate this working theory state of mind. I wrote about this earlier. I think most children keep working models about things they don't understand. Probably this is why small children keep asking many questions. And parents laugh hard when the children's models of things are far removed from reality. But this is no laughing material. We should be encouraging them to have more working models about everything, and keep testing and refining them.

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