Berachos 28a - Tefillas Arvis R'shus Oy Chovah - Part IV

Gemara: [During a conversation between Rabban Gamliel and Rabbi Yehoshua, Rabbi Yehoshua said,] "Woe to the generation that you lead! Because you don't know the pain of Torah scholars, where their livelihood comes from and where their food comes from."
It seems to me that there is an enormous lesson in this statement. A leader leads not only because of his capabilities. A leader must know the troubles and problems of those he leads. He must empathize with them. From the context of Rabban Gamliel's original statement to Rabbi Yehoshua, "From the walls in your house [which are black from soot] it is obvious that you are a blacksmith," (to which Rabbi Yehoshua answered this statement about leaders), we see that Rabban Gamliel should have known by himself that Rabbi Yehoshua was a blacksmith. We see that a function of leadership is concerning yourself with the welfare of those who are following you.
Someone once said, "It's lonely at the top of the ladder." A true leader is always in touch with the bottom of the ladder, too.