my favourite questions to ask:

Is there an educational project you would recommend to develop a good intuition about X?

expediting learning by doing

If you could summarise all there is to learn about X, what comes to mind?

one way to distill expert knowledge in the context of humans

What was surprisingly difficult about doing/learning X?

helpful for normalising beginner struggles and making difficult problems less intimidating

What were the mistakes you did not expect to make in the first few iterations of X?

getting over beginner mistakes asap and gaining momentum to the difficult parts

I’m confused as to why X? Knowing Y, I would expect Z to be something and not X - What am I missing here?

expressing my train of thought this way helps the explainer realise the flaws in my understanding better and help me understand faster

What is your thinking behind X?

digging deeper into where someone's idea, decision or action came from provides useful context in understanding thought processes that result in outcomes/behaviour

Why is X important?

unravels the rationale for underlying core concepts that are usually not immediately obvious

What is the point of doing X?

the nuance with this question from the previous is in its utility. This question usually reveals relationships between concepts and ideas. Often this helps connect the dots

Is the difference between A and B significant? why?

sometimes the differences do not matter as much as we think; other times, the nuances revealed in juxtaposition are non trivial