Asher is translated as “when,” alluding to the fact that it happens that even the high and mighty leader sins. Chazal further translate it as being connected to ashrei, fortunate. This motivates Chazal to assert that a generation whose leader seeks atonement for his unintentional sins is fortunate, because this means that he will surely repent his intentional sins. Chazal underscore the good fortune of a nation whose leader concedes and seeks atonement for his fallibility. On the one hand, this is an enviable character trait – one to which more leaders should ascribe – but, at the end of the day, it challenges our intuition. Does anyone really want a leader who errs – even if he confesses his errors? Is leadership, in fact, strengthened by admitting fallibility? Bringing this idea closer to home from a practical perspective, we should ask ourselves if a child or student feels secure with the knowledge that the one who is in charge of guiding him concedes a mistake? Does this awareness inspire confidence? Humility is not only great, it is critical, but does one seek a leader who fails – regardless of his humility in sharing his indiscretion with us?
Obviously, Chazal are not lauding failure on the part of leadership; rather, they are emphasizing the critical importance of the truth. A nation needs clarity – students and children do not thrive on ambiguity. Be it in the world of chinuch, parenting or national leadership, perfection may be at a premium. Imperfection can be tolerated, however, even accepted, as long as authenticity is present. A parent, teacher, or leader who shies away from admitting error teaches a flawed lesson. He intimates that authority must be protected at all costs – even at the expense of honesty. Such a message inspires fear and even cynicism. It will never inspire respect. Thus, when an educator, parent or leader sincerely acknowledges an error on his part, he is buttressing his ability to teach, guide and lead.
Humility is not a sign of weakness. On the contrary, Moshe Rabbeinu was the paragon of humility – yet, he acted decisively as a leader. When people see their leader choosing emes, truth, over self-preservation, they respect him for what he is – not what he is not. When a child hears the words, “I was wrong,” from a parent, a transformation occurs. The child learns that saying the truth, acting with honesty, is not threatening. Correction is not humiliation. We all make mistakes. The greatest mistake is the cover-up. A leader should strive for – but not be rooted in – the illusion of perfection; rather, he should focus on honesty, integrity and yiraas Shomayim. The Torah/Chazal alludes to such a leader with the word ashrei, fortunate is the generation whose leader concedes his fallibility.
