God commands Moshe to ascend a mountain to view the Land which he will not enter. Moshe asks that God appoint a leader to continue after Moshe’s death so that Bnei Yisrael will not be like sheep without a shepherd. Why does this need to come from Moshe’s initiative? How could it be that Bnei Yisrael would be without a leader? We examine various commentator’s perspectives on this episode. Is this a way of continuing Moshe’s relevance? Or is this a painful reminder that Moshe will not be entering the Land? Moshe’s response exemplifies his positive vision of the future. We examine the strange wording of Moshe’s request and God’s response. Linguistic ties to the episode of Korah provide us with a reminder of the type of leadership Bnei Yisrael will need -one of checks and balances-, and the challenge of transferring leadership from Moshe.