The charming lady asking me this has been fortunate in her experiencing!
I have noticed there are two motivations for asking a teacher questions.
The first is an honest and open attempt to understand a concept, and is characterized by open questions, of the “Would this mean…..?” type, amongst others.
The second is an attempt to demonstrate the shortcomings in the teacher’s material, and to have the teacher substitute some of the “questioner’s” own superior material in it’s place. “Surely you don’t mean that ….?” might be one way this can appear.
Mostly questioners fall into one or other of these groups. However some flop about a bit. The teacher and aware onlookers can amuse themselves by watching closely for the transition point, at which time it is pointless to go further if the questioner is moving from type one to type two. On those rare occasions the movement is from type two to type one, then it would signify a real opportunity for the questioner to expand their knowledge and understanding, and the atmosphere immediately changes.
Either way, of course, the teacher will come to a greater understanding of the needs and capabilities of the questioner, and will act to bring the student to a greater awareness of their true nature by whatever means possible.
So, it’s good to question, but that doesn’t mean that the benefit will be in the answer (if given).