Photo Credit: Jewish Press

People make mistakes. Leaders are people. Therefore, leaders make mistakes. What’s fundamentally different about leaders is that their mistakes are likely to impact many other people in significant ways. In addition, leaders often take way too long to recognize and admit they are wrong. This reluctance amplifies their errors and increases their hurtful consequences.

Today many organizational board members understand the importance of preventing mistakes from the outset and, when they do occur, the need to identify and correct them as soon as possible. This is true regardless of whether the errors are strategic or tactical in nature. For example, a company that launches a new product and experiences poor market response must acknowledge the problem in a timely manner and identify the level or nature of the error. (Was the problem with the product per se or perhaps with its marketing and distribution?)


To prevent major errors and problems, organizations, ranging from the military to Fortune 500 companies, have begun to call in “Red Teams” to identify potential problems and weaknesses ahead of time. One of the major methods “Red Teams” employ is to propose alternative analyses as a major issue can be a decision maker’s own cognitive biases. “The objective of alternative analysis is to hedge against these natural human and organizational constraints by using liberating structures or structured analytic techniques, or by employing a wholly different team not already immersed in an issue to challenge assumptions or present alternative hypotheses and outcomes” (RED TEAM: How To Succeed By Thinking Like The Enemy by Micah Zenko, 2015, p.xxiii).

Zenko explains that for red teaming to be effective certain basic guidelines need to be followed. The first and most important is that the boss must buy in. “First, bosses must recognize that there is a vulnerability within their organization that red teaming can help uncover and address…. Indeed, in many instances, a readily apparent failure or disaster must have already occurred – resulting in meaningful human, financial, or reputational costs – before a boss will willingly listen to appeals for red teaming” (p.3).

We see clearly that a leader’s openness to the possibility that he might make mistakes and his readiness to acknowledge these mistakes is paramount to an organization’s survival and its ability to thrive. Unfortunately, history is replete with examples of leaders who did the opposite. This week’s parsha, however, showcases a leader who understood this and taught it to the world.

After the brothers sold Yosef into slavery the Torah records the episode of Yehuda and Tamar. When Tamar, who was found guilty of immoral behavior by Yehuda’s court, is about to be executed, she sends Yehuda’s staff and signet to him, claiming that the owner of these items is the responsible party. Yehuda, in an act of moral courage, readily admits his sin and saves Tamar from death. With the words “tzadkah mimeni,” Yehuda determined the course of Jewish history. Chazal praise both Yehuda and Tamar for their actions: Yehuda for accepting responsibility and saving Tamar, even though he could easily have denied any wrongdoing and been believed, and Tamar because she refused to accuse Yehuda explicitly. If Yehuda refused to admit his error she had decided to suffer the consequences rather than embarrass him.

Many commentators explain that Yehuda’s admission of error refers to his decision to execute Tamar and his subsequent acceptance of personal responsibility, thus saving her from death. However, the Rashbam and Seforno explain that Yehuda’s declaration refers to the initial incident when he refused to let Tamar marry his third son. According to this explanation, Yehuda was acknowledging his original mistake.

This approach adds another dimension to Yehuda’s greatness. After all, we would expect nothing less of Yehuda than to save an innocent person, even at his own expense. But Yehuda’s true leadership was demonstrated when he was able to look back to the original incident and identify his mistakes. Such strength of character is regrettably all too rare. Yehuda taught future generations the importance of leaders painstakingly searching for their mistakes, identifying them quickly, and rectifying them immediately.


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Rabbi Dr. David Hertzberg is the principal of the Yeshivah of Flatbush Middle Division. He is also an adjunct assistant professor of History at Touro College. Comments can be emailed to him at