At the end of his life, Moses makes two requests of God concerning leadership in the Land of Israel: one, in this week’s parsha, that he be allowed “to cross over and see the Good Land beyond the Jordan River,” where he presumably can continue to lead [Deuteronomy 3:23-25]. God’s response: “You must command Joshua, strengthen him and give him resolve, for he shall cross before this nation and shall bring them to inherit the Land” [Deut. 3:28].
The second request came in Pinchas, “Let (God) appoint a leader over the witness assembly” [Numbers 27:15-16], a request coming after the Torah informs us that the daughters of Tzelafhad can inherit their father’s share [Num. 27:11].
Listen to the words of the Midrash: “What caused Moses to request his replacement, after [the story of] the daughters? Since these daughters inherited their father, Moses declared, ‘This is the right moment for me to claim my need. After all, if these women can inherit [their father] my sons should certainly inherit my glory.’ The Holy One, blessed be He, said to him: ‘… Your sons sat idly by themselves and were not occupied in the study of Torah. Joshua, on the other hand, served you well and extended to you much honor. He would arrive at your courthouse early in the morning and leave late at night. … Appoint Joshua the son of Nun as your successor, to fulfill the verse, ‘the guardian of the fig tree shall eat of its fruit’” [Proverbs 27:18].
Both requests by Moses are denied. That his children be his successors is denied because his sons are found wanting. Perhaps Moses understands that he himself bears some guilt for the flaws in his children. After all, he is so consumed with his relationship with the Divine that he doesn’t seem to have the time or the patience for family.
Moses apparently is more comfortable requesting that he be allowed to enter the Promised Land. Does he not deserve to reach his life’s goal, enter the Land of Israel, and begin this new era of Jewish history with himself as leader? And yet, that request, too, is denied: “And the Lord was angry at me because of you, and He did not accept my plea … saying that I may not speak of this anymore” [Deut. 3:26].
Perhaps both rejections emanate from the same source, and Moses is really blaming himself. Remember that when God had originally asked Moses to assume the leadership of the Israelites, Moses demurred, claiming to be kevad peh, “heavy of speech” [Ex. 4:10]. And then the Bible testifies that “the [Israelites] did not listen to Moses [about leaving Egypt] because of impatience and difficult work” [Ex. 6:9]. Most commentators explain that the Hebrews had no energy to resist their slavery; the hard work of servitude sapped their inner strength and prevented them from even dreaming about freedom. But Ralbag [1288-1344] explains this to mean that it was because of Moses’ impatience with his people [the Hebrews], because of his difficult work in making himself intellectually and spiritually close to the Divine.
Moses was into the “heavy talk” of communicating with God and receiving the Divine words. He did not have the interest or patience to get into the small talk, the necessary public relations of establishing personal ties and convincing one Hebrew after another that it was worthwhile to rebel against Egypt and conquer the Land of Israel. He was a God-person, not a people-person, or even a family-person. He’s not blaming them; he is ultimately blaming himself. He spent his time communicating with God, receiving God’s words for the generations; as a result, Moses sacrificed his ability to move his own generation to accept God’s command to enter the Promised Land.
A leader must share the destiny of his people. If they could not enter the Land, even if it was because of their own backsliding, he may not enter the Land, because he did not succeed in inspiring them.
The very source of Moses’ greatness — his lofty spirit and closeness to God — was what prevented him from getting down to the level of his congregation and family to lift them up. Moses succeeded like no one else, before or after him, in communicating God’s word for all future generations; but he did not do as well with his own generation. Hence his words are honest and very much to the point: “The Lord was angry at me because of you” — because I did not have sufficient time to deal with you on a personal level, to nurture and empower you until you were ready to accept God’s teachings and conquer the Promised Land.
Perhaps Moses’ requests were denied in order to teach us that no mortal, not even Moses, leaves this world without desires unfulfilled. And perhaps he was refused merely to teach us that no matter how worthy our prayer, sometimes God answers “No,” and we must accept a negative answer.
Faith, first and foremost, implies our faithfulness to God, even though at the end of the day He may refuse our request.
As taken from, https://jewishweek.timesofisrael.com/when-gods-answer-is-no/