The verse seems a little awkward . Why not simply say that proper leadership is required so that the people will not be like shepherdless sheep כצאן בלי רועה? Why the extra words?
The literal meaning of the posuk is "they not be like sheep that there is no shepherd to them.”
Reb Zalman Sorotzkin explains that Moshe had no doubt that a leader would emerge. While there is never a shortage of potential leaders, most candidates will cater more to themselves than to the needs of the people. The people might have a shepherd but not one that will be to them for them; instead, he might be one with his own interests in mind. Moshe's request was that they get a leader who will be only concerned with them.
As Rav Yaakov Yuzef explained, there are two kinds of shepherd: one that does it just to make a living & one that does it because he cares about the well-being of the sheep. The latter will make sure that whatever he does is for the benefit of the sheep & not what's better for his bottom line. This is the kind of leader we need!
Reb Shalom Schwadron tells us a story about one of our leaders that personifies this trait. There was a Talmudic student who got very sick. As time went by, the doctors gave up hope & each passing day his condition worsened. The student went to his Rebbi, the Chafetz Chaim, to ask for a Bracha that he should recover. The Chafetz Chaim answered him that he will give him a way out of this sickness on condition that he never tell anyone what it was. The student readily agreed.
The Chafetz Chaim told him to go to an unknown scholar who lived in a tiny town far away and tell him your situation. He will give you a Bracha & with Hashem's help you will be healed. The young man immediately went to that town to search out that talmid chacham. He found him & explained to him what was happening, got his bracha & went back to Radin, to yeshiva. Within a few short weeks, he was completely healed & continued his studies in the Yeshiva.
Eventually, he married, moved away, raised a family & never told anyone what happened to him. Some twenty years later, his sister in law became sick with the same sickness he had all those years ago but he didn't say a word. His wife, though, remembered that he had been sick & asked him how he got better. However, he refused to answer. His wife kept pressuring him to reveal the secret that she felt might save her sister yet he still didn't answer. The wife & sister didn't stop pressuring him thinking that this secret would save her life until he finally couldn't take it anymore.
He thought to himself that after all these years, he had already fulfilled his promise to the Chafetz Chaim & he told them what happened. His wife & sister were then filled with hope that this would be their salvation. A short time later he began feeling ill & became very afraid. He traveled to the Chafetz Chaim who was by then very old & weak. As the man told him his story, the Chafetz Chaim listened silently. Finally, he broke the silence & said in a broken voice, "I wish I could help you again but what can I do? When you had the sickness the first time, I fasted for forty days so that you would get better. Now, I'm too old & weak to do it again.
This is a leader! Not only did the Chafetz Chaim fast for forty days for one student but he orchestrated the whole thing to look like it was because of someone else's blessing. He didn’t even take credit for helping him. That is what should be the leaders of the Jewish people. May we all merit to be under the guidance & influence of such leaders!
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