Discovering an Overlooked Quality of Successful Leadership

Baltimore, MD - Apr. 29, 2026 - Leadership touches everyone. Even if we don’t hold a formal position, opportunities to lead arise in everyday roles—for example, every teacher and parent is a leader. Leadership may be assigned in specific scenarios—school, yeshiva, shul, or the workplace. Much has been said and written about what makes a good leader. Here, I want to share one invaluable insight about leadership that, in my experience, is not well understood: A successful leader conveys a message that people can receive.

I recently read biographies about two tremendous talmidei chachamim. Each one was a leader. One succeeded, while the other failed. Both men were great in their own right and much above our level. It is not our place to judge or critique them. But it is our responsibility to remember their stories and derive lessons from them.

Rav Yaakov Yosef was born in Lithuania in 1840 and eventually became the magid meisharim (preacher) in Vilna. He was a product of the Volozhin yeshiva and a world-class talmid chacham. He was also a disciple of Rav Yisrael Salanter and a noted mussar personality. Due to his impeccable credentials, Rav Yosef was eventually offered the prestigious position of Chief Rabbi of New York City. He was brought in from Vilna to create a central rabbinic authority in America to raise the standards of kashrus and Jewish education in New York specifically and the United States in general. When Rav Yosef arrived on the shores of America in 1888, he was greeted with tremendous excitement and honor. When he gave his first public address, throngs of Jews flocked to hear his words, and the police were needed to maintain order. The state of kashrus at the time was appalling, and Rav Yosef removed many shochtim from their positions and replaced them with properly trained G-d fearing shochtim. He also put many important kashrus policies into place.

Yet opposition against Rav Yosef began to rise. Many individuals were angry that they had lost their jobs because of him. Matters went from bad to worse when he added a nominal 3-cent fee to kosher meat to cover the cost of plumbas (irremovable seals). He was falsely accused of charging extra to fill his own pockets. Pamphlets circulated that publicly shamed the chief rabbi. Eventually, Rabbi Yosef’s salary was discontinued. The opposition against Rav Yosef turned into derision of him and his battle for kashrus. This eventually caused Rav Yosef to suffer a stroke in 1897 and led to his untimely death in 1902 at the age of 62. It was only at his funeral and its aftermath that the masses felt remorse for how they had disgraced and pained this great tzaddik, and different groups fought for the honor to bury him in their respective cemeteries and to eulogize him properly. The details of this tragic story are discussed in The Rav Hakolel and His Generation (Landau, 2011).

Of particular interest is that throughout all of the fierce battles against Rav Yosef, he never responded in kind. As a student of mussar of the highest order, he remained level-headed and respectful while not compromising on his principles. Part of the great tragedy of this saga is that neither the scholarship, piety, nor humility of Rav Yosef allowed him to succeed in his mission. This exemplary tzaddik and talmid chacham left this world disgraced and humiliated by his own people. The story of Rav Yakov Yosef is not discussed often, as it is one of the great humiliations and failures of American Jewry in its early years. Yet it is true and part of our heritage, whether we choose to remember it or not.

Soon afterward, I read A Blaze in the Darkening Gloom: The Life of Rav Meir Shapiro (Boimel et al., 1994). Rav Shapiro was born in 1887 and lived most of his life in Poland. He was a prodigy known for his brilliance, wit, and oratory. As a child, he witnessed the derision of yeshiva bachurim and the dreadful conditions in which they lived, causing some of his colleagues to leave the fold of Orthodoxy. After witnessing this firsthand, Rav Shapiro made it his life goal to build yeshivos and elevate the esteem of Bnei Torah.

Rav Shapiro held many positions during his lifetime. What is most remarkable to me is how, in every rabbinical position and every campaign, he won the hearts of the masses. A remarkable illustration of this is when he accepted the position as rabbi of Sanok, a city known for great dissension among the various factions, to the extent that no rabbi wanted to take the position. After Rav Shapiro’s first public speech, he had won their respect. His first goal in every city was to raise the standard of kashrus, mikvaos, and eiruvin. When he put in a new policy for the butcher shop in Sanok, he tactfully stood his ground against opposition on the first day and was not subsequently challenged. The story of his life is success after success, and he transformed communities until he eventually fulfilled his dream of establishing Yeshivas Chachmei Lublin, a yeshiva for the most brilliant students in Poland, with a state-of-the-art dormitory, kitchen, dining room, library, and even a model of the Beis Hamikdash for students to observe to assist their studies.

It is not our place to compare and contrast these two Torah giants. Yet, an undeniable observation about Rav Meir Shapiro is that he had tremendous charisma and his words were well received. He always seemed to know what to say and how to say it. Not only that, but he knew how to adjust his style to fit the person with whom he was dealing. One of the struggles in Rav Shapiro’s life was his attempt to maintain the financial support for the massive expenses of Chachmei Lublin. He was forced to travel around Europe fundraising, and he eventually needed to fundraise in America. At first, he was not successful in America. However, once he discovered the American mentality about advertising, he changed his approach and brought in a tremendous amount of money from the trip.

Rav Meir Shapiro knew the secret of speaking the language of the people. He knew what inspired them, what made them laugh, and what spoke to their hearts. He won everyone’s respect and admiration, and transformed his enemies into his supporters. He knew which battles to fight and which to ignore.

If we analyze the complaints that led to the opposition to Rav Yosef, we see how the masses didn’t understand his motives and lost respect for him. Rav Yosef had accumulated a great amount of debt in Europe due to the large sums of tzedakah that he distributed. Before he came to America, he stipulated that the community of New York would pay off his debts; otherwise, his creditors would not let him leave Vilna. The community also offered him a luxurious apartment and a substantial salary, as befitting the chief rabbi of New York City. This led to the false perception that Rav Yosef was driven by money. When he fell out of favor with many butchers whom he removed from their positions, and then added a nominal fee for kosher supervision (something unheard of in those days), there was fertile ground for unscrupulous individuals to claim that he was imposing on them in order to increase his personal bank account.

There were other factors that worked against Rav Yosef as well, including the fact that many wanted a different rabbi to become the chief rabbi and that he didn’t speak English. What emerges is that he literally and figuratively didn’t speak the language of the people. Through no fault of his own, he was brought in to raise a level of kashrus for a people who weren’t ready for his standards and who didn’t perceive the altruism of his actions.

The Satmar Rav commented that we see with our 20/20 hindsight that effort should have first been put into the chinuch of the next generation. If a new generation had been instilled with the value of halachah and respect for rabbonim, they would have been receptive to the implementation of changes in the kashrus industry.

From this we clearly see that successful leadership depends on the perception of the followers. If they respect their leader and are inspired by his message, they will be receptive to his interventions. But if the leader’s words do not resonate with his followers; if his actions are perceived as being driven by personal motives; if he is seen as out of touch or unrefined; then he will not succeed. It doesn’t matter if his words are true, his motives pure, his insight precise, and his conduct impeccable – for if the people are blind to that, they will not respect, accept, or follow him.

To whatever degree each and any of us are leaders, we must internalize this principle. The greatest of people can know that they are right and proceed to start a campaign or wage a war. We must remember that the right motives and the most sterling middos alone are not the key to success. We must ask ourselves what our followers are able to receive, how they will perceive us, and what speaks to them. As the Torah cautions (Bamidbar 32:22), “You shall be clean in the eyes of Hashem and the Jewish people.” It does not suffice for Hashem to know that our actions and intentions are pure; it is our responsibility to ensure that people recognize this as well. And as the Chasam Sofer writes (Teshuvos 6:59), it is more difficult to fulfill the latter obligation than the former.