Moses knew that feeling all too well. As he approached the end of his time, he had one burning question for God: "Who will lead Your people after I'm gone?"

This question forms the heart of a fascinating passage in Shir HaShirim Rabbah, a Midrashic commentary on the Song of Songs. Rabbi Berekhya interprets the verse "May the Lord, God of the spirits of all flesh, appoint [a man over the congregation]" (Numbers 27:16) as Moses's plea. He wasn't just asking for a successor; he was asking God to reveal the kind of shepherds He would place over His children.

Moses essentially says, "Master of the Universe, since You're ousting me, tell me who these new shepherds will be!" The text then cleverly links this to the verse in Song of Songs (1:7): "Tell me, he whom my soul loves, where do you herd, where do you rest your flock at noon? Why [shalama] should I be as one bound [keoteya]?"

What does this seemingly romantic verse have to do with leadership? Well, the Midrash unpacks it beautifully. Moses is worried about the future. He asks, "Where do you herd during the monarchy? Where do you rest your flock at noon, when Israel is subjugated to foreign kingdoms?" In other words, how will you care for them in times of both prosperity and hardship?

Rabbi Azarya offers a powerful interpretation of the wordplay: Shalama, that I will not [shelo] become as nothing [lema] in the eyes of Your companions regarding their flocks. He fears a chillul Hashem, a desecration of God's name. It would be a terrible thing, he argues, if God's children were suffering while the nations around them were thriving. It brings to mind the age-old question: if God is just, why does evil exist and why do the righteous suffer?

Rabbi Yudan bar Simon adds another layer, suggesting that the nations might accuse God of injustice. They might say, "God knew He would slaughter them in the wilderness, and so He did!" This refers back to the episode with the spies (Numbers 14), where Moses had to implore God not to destroy Israel, lest the nations think He was simply unable to conquer Canaan.

The Rabbis offer a further concern: that the Israelites, seeing their own suffering, might deviate [yatu] from following God and instead cleave to the ways of the nations, just as the verse says, "Can the seat of wickedness be Your companion?" (Psalms 94:20). The fear is that hardship could lead to spiritual abandonment.

God's response to Moses is both comforting and challenging. He says, "Moses, you ask Me where I herd and rest My flock? By your life, if you do not know, ultimately, you will know!" This is linked to the next verse in Song of Songs (1:8): "If you do not know, fairest among women..."

The Midrash interprets "fairest among women" as "fairest among prophets," the most outstanding of them all. Rabbi Yosei bar Yirmeya then offers a striking comparison: Why are prophets likened to women? Because, just as a woman isn't shy about demanding her household needs from her husband, the prophets aren't shy about demanding the needs of Israel from their Father in Heaven.

So, what does this all mean for us? It's a reminder that leadership, whether divine or human, requires deep empathy and a commitment to justice. It's about ensuring that those under our care are nurtured, protected, and guided, especially in times of adversity. And like Moses, we should never be afraid to ask the tough questions, even of the Divine. Sometimes, the most profound answers come from daring to voice our deepest concerns.