Moses retells the story of the appointment of the judges that took place 40 years earlier. It is puzzling that Moses told the judges that any question which is too difficult for them to answer shall be brought to him. This seems like a lack of humility, asserting his superiority in claiming that he could resolve any problem that perplexed lesser judges. Wasn’t Moses described as the most humble of all men?
Rabbi Hanina famously said, “I have learned much from my teachers, more from my colleagues, and most of all from my students”. As the student raises questions to which the teacher must find answers, the subject at hand becomes much clearer to the teacher, and he achieves a depth of understanding unattainable on his own.
When the great sage Rabbi Yohanan’s disciple, Rabbi Shimon, died, whenever other students would find authoritative sources that supported Rabbi Yohanan’s teachings, the rabbi would weep bitterly saying “Rabbi Shimon constantly challenged everything I said and so I would have to rethink and explain my position until it became crystal clear to me. I do not need anyone to support my statements. I need someone to challenge them!”
Moses, too, wanted to be questioned and challenged so that he would be compelled to analyze each law, and thereby achieve a maximum understanding of it.
The attitude of a student must always be to seek greater understanding by questioning his teachers, and the teachers attitude should be to welcome challenges, in this way both the student and the teacher are stimulated to achieve greater understanding.