We learn in Avos that “the bashful one does not learn”. One of the character traits of the wise is that regarding a matter which he has not heard, he says “I have not heard”. He also asks to the point. One needs sense to be a questioner for as the Zohar says, they would punish in the Yeshiva shel Maalah one who would embarrass his teachers by his questions. Likewise, the Gemara discusses one student, who would question his teacher all through the year but during the discourse at the time of the pilgrimage he would not ask because his teacher was preoccupied and may not have been able to answer him appropriately and he would therefore be embarrassed in public.
If this is so, one needs proportion, not to ask a wise man in public and specifically not to question a guest who has come to town unless it is clear and well known that he is a great man and able to answer any matter.
Any person who has a Rav, or if a sage comes to his place, should neither weary nor tire from asking him all his questions and difficulties. He should do nothing big or small without asking a wise man and without the advice of a wise man, in order that he should be wise in all he undertakes, in which case he will be successful in all his ways and become wise himself.