When Moshe is told that he will soon pass away, his first request is to selflessly solicit G-d to appoint someone to take over as leader of the people (27:16). Moshe asks for someone who will “lead the Jewish people out and bring them in so that G-d’s congregation should not be like sheep without their shepherd” (27:17). Rav Yaakov Meir Schechter asks why Moshe phrased it as if the sheep possess “their” shepherd. Wouldn’t it be more appropriate to say “like sheep without a shepherd”?
Rav Schechter explains that Moshe requested a leader that was part of the people, who would feel their pain and understand their struggles. Moshe knew that people need a leader that will not only lead them but also be able to relate to them and advocate on their behalf.
Moshe demonstrates two critical components of effective leadership: 1) Thinking selflessly about others as he advocates for his successor even though he will not benefit from this new leader, and 2) intimately and personally appreciating the plight and struggles of the people he leads and represents.