Rav Chaim Voloshner (Ruach Chaim 1:4): … It is prohibited for a student to accept the words of his teacher if he has questions about them. Furthermore sometimes the truth is with the student and not the teacher.” Avos (1:4) says, One should sit in the dust at the feet of one’s teachers and drink with unquenchable thirst what they say. “The word for sitting - avek - can also mean struggle or warfare. That is because this is an obligatory struggle. The holy rabbis who have composed the books we study have in fact given us permission to struggle and to fight over their words and to answer the difficulties they raise. Therefore, we have the right to question what they say and not to blindly accept their words - but one must love the truth…. Since ascertaining the truth is the prime concern - we must be very careful not to be conceited and egotistical in the discussions and to imagine that we are as great as the teacher or author with whom we are disagreeing. We should be aware in our hearts that we might simply be misunderstanding their words. Therefore we must always be very humble. We must have the attitude, ‘I am not worthy to argue but this is Torah and I must know the correct answer’. Furthermore, the Mishna states that the struggle is conditional on being ‘in the dust at their feet’ which means we must be humble and submissive and figuratively sit on the ground before them in these discussions.
Seridei Aish (1:113): I frequently comment on the apparent contradiction found in Avos (6:5) concerning those factors involved in acquiring Torah i.e. analysis of the students and faith in our Sages. Furthermore, what does faith in our Sages have to do with acquiring Torah? However, the explanation is that if one doesn’t believe in the truth of the words of the sages then one readily dismisses them for the slightest reason. With an attitude of condescension, one proclaims that they didn’t know what they were talking about. Consequently, one makes no effort to investigate and try to validate what they said. However, in the end we find that in fact we are the ones who have erred. … Therefore it is characteristic of the truly wise to presume that the sages have not erred, G d forbid! In fact we, with our limited perspective and limited understanding, have erred. On the other hand to blindly believe and not struggle to comprehend with our intellect the apparent difficulties, saying simply that they knew and we need merely to mindlessly rely on them, that is also not correct. We need to wrestle mightily with the apparent contradictions and doubts as if they are people like us. With this approach, we will come to a much profounder and sharper comprehension. Thus, we see that both factors - emunas chachomim (faith in our sages) and pilpul (intellectual evaluation) - work together to the purpose of the acquisition of Torah.
Maharal (Introduction to Be’er HaGolah): The precondition for achieving perfection, through knowledge and comprehension of reality, is accurate self evaluation. However self knowledge is not easily achieved and in fact it is rare to find someone who has an objective understanding of whom he is. Paradoxically this should be the easiest thing to know - he needs to simply open his eyes. He is not far away and is not in Heaven - in fact, there is nothing closer! However, the majority of people perceive themselves inaccurately. In particular, they mistakenly think that they are the equal of the early sages and say, “I also have a brain and that the early days were not better than now.” They insist the intellect of man is identical in all ages. True sages, however, know their own value. They do not distort justice concerning their money and surely concerning themselves. An example of this accurate self-evaluation is found in Eiruvin (53a): “The hearts of the early generations were as open as the 20 amos wide door of the Ulam of the Temple, while that of recent generations is like that of the 10 amos wide door of the Heichal of the Temple while our heart is like that of the eye of a needle….” We see that they are not embarrassed to admit their inferiority relative to earlier generations and describe how they differ….
