What is the most important characteristic necessary for a leader?
Yehoshua, the most dedicated and trusted student of Moses, was chosen to replace Moses not because of his intellectual prowess, study habits or meticulous following of his teacher, but surprisingly, our sages say it was because he had the ability to interact according to the character of every individual.
A leader who is too removed and out of touch with the people cannot function as a leader. If his spiritual perfection denies him the ability to interact and empathize with the average person, he is suitable to lead angels, but not humans, whose needs require the empathy of the leader.
Rabbenu Chaim Halberstam (1793-1876) was acclaimed by the leading rabbis of his generation as one of the foremost Talmudists, Judges, and Kabbalistic authorities of his time. He received queries from Rabbis and communities from all over the world. He was also known for his limitless charity. One time, his student complained that he saw an elderly woman to whom the rabbi had given charity, spend the money on purchasing duck, which was very expensive and a delicacy, and definitely not an essential of life.
“I am so pleased that you informed me of this,” he told his student. “Now I know that I must give her enough money to buy duck, since this is one of her needs.”
What is true of the relationship of the leader to the community is also valid, on a lesser scale, in the relationship of one person to another to utilize our natural innate empathy to understand and empathize with others.