You’ve hit on some of the keys: a deep respect for the person you are questioning and an invitation to reflect (a la the blank face).

A few other aspects of good questioning that I strive for: a posture of genuine curiosity, questions without a “correct” answer, and similarly, questions that could be answered in many ways.

A good question should walk the line between ordinary and bizarre. A good question should be unusual.

I was listening to the abridged CD version of Daniel Goleman’s
Primal Leadership
in the car today. He said that for an executives to learn something really new, they need learning experiences that are both relevant and framebreaking. To be relevant, the experiences must be sufficiently familiar. To be framebreaking, they must be sufficiently unfamiliar. Goleman cites a colleague who says that to provide learning experiences, you have to constantly manage your PWI — your “Perceived Weirdness Index”.

If I combine your thoughts and Goleman’s, I find another quality of good questions: A good question provides a learning experience.

By the way, thank you again for recommending the book
Narrative Therapy. It’s a great source of ideas about asking good questions. I’ll review it here one of these days.

That said, doesn’t the question of whether your question was good or not (if you see what I mean) depend on your goal? As a coach, your goal is to help others learn and grow, hence good questions are those that help others learn and grow. A cross-examiner might define a good question as one that the witness wasn’t prepared for, or one where the answer reveals more than their opponents wanted. A researcher might define a good question as one that opens up new avenues of research and suggests new possibilities (reveals new problems).

This still doesn’t answer the question of how to ask good questions …