"And you shall select from among the entire people, men of wealth who are G-d fearing, men of truth who despise monetary gain" [Yisro 18:21]
Why, asked the Kotzker Rebbe, did Moshe Rabbeinu appoint ''leaders of thousands, leaders of hundreds, leaders of fifty and leaders of tens''? Was he not afraid that perhaps such an appointment might offend some of them if they would be appointed to a post of lesser status than that of their fellows?
However, answered the Kotzker, remember that the Torah describes these individuals as being ''men of truth''. A man of truth knows that honor is a lie and an illusion. Therefore none of these individuals felt offended by seeing someone else receive a higher position than they.
Source: Rabbi Yisrael Bronstein
And - besides that, those that are leaders of the smaller groups would actually be able to make more of an impact and help those that he is assigned over. In effect, doing more good! This is a greater good and a "true honor" than just having a passing influence over a greater number of people.
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