I know in school they tell you that there is no such thing as a bad question. In part, that's true because its always better to ask questions than to not ask questions. Asking questions is a very important tool for continuing to learn, to understand others, to improve and sharpen your game.
However, there is such a thing as asking the wrong question. And unfortunately, asking the wrong question will lead to the wrong answer. Let's say I am experiencing a great deal of job dissatisfaction. It'd be tempting to ask myself, "Should I quit or should I stay with this job?" When, really, the better question might be, what specifically is not working for me about this job and what can I do about that? When all of the possible solutions have been explored and implemented and there is still job dissatisfaction, then it might be time to ask whether its time to quit. But jumping to that conclusion without first doing the work of exploring the right questions perhaps could lead in the wrong direction.
I know for myself that at times I have needed help from others to even know what the right questions to ask really are. I think identifying the best questions to ask in any given situation, happens best in community. One of the downfalls of our individualistic society is that we tend to go it alone when making decisions, or we invite people in to help us discern but the questions that are posed by us in the first place aren't even the right questions because we developed the set of questions on our own. We say, "Help me know whether I should (fill in the blank) or if I should (fill in the blank)" when there may be a different set of questions that would be more helpful. Backing up a step, and saying, "Together, let's figure out what are the questions that need to be asked in this situation" is more likely to lead towards a path with more optimal, growth producing outcomes.