Faith in Heaven, Doubt on Earth

The Midrash imagines a dialogue between Moshe and God that goes as follows:

"דָּבָר אַחֵר, הֵן קָרְבוּ יָמֶיךָ, לָמָּה נִגְזַר עָלָיו מִיתָה בָּזֶה הַלָּשׁוֹן הֵן, רַבָּנָן אָמְרֵי לְמָה הַדָּבָר דּוֹמֶה, לְאֶחָד שֶׁכִּבֵּד אֶת הַמֶּלֶךְ וְהֵבִיא לוֹ דּוֹרוֹן, חֶרֶב חַדָּה. אָמַר הַמֶּלֶךְ הַתִּיזוּ אֶת רֹאשׁוֹ בָּהּ. אָמַר לוֹ אוֹתוֹ הָאִישׁ, אֲדוֹנִי הַמֶּלֶךְ בַּמֶּה שֶׁכִּבַּדְתִּיךָ בָּהּ אַתְּ מַתִּיז אֶת רֹאשִׁי. כָּךְ אָמַר משֶׁה, רִבּוֹנוֹ שֶׁל עוֹלָם בְּהֵן קִלַסְתִּיךָ, שֶׁכֵּן כְּתִיב (דברים י, יד): הֵן לַה' אֱלֹהֶיךָ הַשָּׁמַיִם וּשְׁמֵי הַשָּׁמָיִם וגו', וּבְהֵן אַתָּה גּוֹזֵר עָלַי מִיתָה. אָמַר לוֹ הַקָּדוֹשׁ בָּרוּךְ הוּא שָׁכֵן רָע רוֹאֶה אֶת הַנִּכְנָסוֹת וְאֵינוֹ רוֹאֶה אֶת הַיּוֹצְאוֹת, אָמַר לוֹ אִי אַתָּה זָכוּר בְּשָׁעָה שֶׁשְּׁלַחְתִּיךָ לִגְאֹל אוֹתָן מִמִּצְרַיִם וְאָמַרְתָּ לִי (שמות ד, א): הֵן לֹא יַאֲמִינוּ לִי, הֱוֵי הֵן קָרְבוּ יָמֶיךָ. 

Another matter, “behold [hen], your days are approaching” – why was death decreed upon him with this expression, hen? The Rabbis say: To what is the matter comparable? It is to one who honored the king and brought him a gift, a sharp sword. The king said: ‘Behead him with it.’ That person said to him: ‘My lord the king, with what I honored you, you are beheading me?’ So, Moses said: ‘Master of the universe, I lauded you with hen, as so it is written: “Behold [hen], to the Lord your God are the heavens, and the heavens of heavens…” (Deuteronomy 10:14), and with hen you are decreeing death upon me?’ The Holy One blessed be He said to him: ‘A bad neighbor sees the incomes but does not see the expenditures.’ He said to him: ‘Do you not remember when I sent you to redeem them from Egypt, and you said to me: “But, behold [hen], they will not believe me”?’ (Exodus 4:1). That is, “behold [hen], your days are approaching.”"

Simply understood the Midrash is playing on the word הן with Moshe arguing that he ought not be consigned to death with הן (which connotes finality — see Tosefes Bracha to that pasuk) and not allowed into the land after he employed הן to extol HaShem's greatness with HaShem responding that he's only looking at half the story as he has also used that word to disparage Israel. 

However, I believe the Midrash is pointing to a deeper message:

Throughout Moshe's storied career he repeatedly doubts the people's faith in God and himself as His messenger and their ability to fully discard paganism. 

See, e.g.:

• Shemos 4:1 "But they will not believe me or listen to my voice."

• Ibid 17:1-4 "What shall I do with this people? They are almost ready to stone me."

• Bamidbar 11 "Did I conceive all this people? Have I brought them forth, that You should say to me, carry them... I am not able to bear all this people alone."

• Devarim 31:27 "For I know your rebellion and your stiff neck. Behold, while I am still alive with you today, you have been rebellious against the LORD; how much more so after my death!"

• Ibid Ibid:29 "For I know that after my death you will surely act corruptly and turn aside from the way which I have commanded you, and evil will befall you in the latter days, because you will do evil in the sight of the LORD, provoking Him through the work of your hands."

Even after the catastrophic episodes of the golden calf and the spies, when Moshe indeed effectively pleas for clemency, he doesn't invoke the people's overall goodness, but rather how it would look for God and זכות אבות, respectively.

Moshe doesn't seem to have ever believed in the people. 

People need to be led by someone that not only believes in the cause but also in the people's ability to embrace it. 

Moshe complains to God about how it can be that He isn't allowing him to bring the people into the promised land — the fulfillment of his mission — given all he's done to promote awareness of and bring honor to HaShem's name, with HaShem responding that the merit of the claim notwithstanding, lack of belief in the people is an insurmountable disqualifier to leadership.

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