A recent 60 Minutes segment focused on the Giving Pledge, the commitment made by some of the world's richest individuals to dedicate the majority of their wealth to philanthropy. In an extensive discussion that touched on issues ranging from strategic initiatives to measuring philanthropic impact, Charlie Rose asked whether this select group of billionaires ever discussed failure in the context of their charitable work. Warren Buffett seemed surprised by the question. With the avuncular candor his fans have come to appreciate, the Berkshire Hathaway chair gently chided his interviewer, "If you bat a thousand you're playing in the little leagues."
To state the obvious, effective leadership comes with the expectation of success. The leaders we admire most are those who accomplish their goals and who complete their missions. And yet one of the great ironies of leadership is that a willingness to experiment, to journey far beyond our comfort zones, and even to risk failure, are hallmarks of bold leadership. Buffett, of course, is completely right. If we play it safe all the time, remaining deeply ensconced in the 'known,' we can certainly appear to increase our success rates. But as every successful leader knows, there is no comfort in the growth zone, and certainly no growth in the comfort zone.
There are, of course, perfectly understandable reasons why many, particularly among those who lead charitable organizations, are excessively prudent when it comes to risk taking and bold decision-making. Leading institutions in today's philanthropic environment often forces us to live in fear of alienating our funders. Wary that we will say or do the wrong thing, we opt for an abundance of caution. We prefer safe to courageous. We worship at the altar of consensus precisely because we are risk-averse. We cannot take the chance of trying and failing when donors want the assurance that their investments are guaranteed. Failure in this context is simply not an option. And so, to echo Buffett, we play in the little leagues.
But playing in the little leagues is for kids. In the history of the Jewish people nothing great ever happened without a willingness to step out on a limb, to take a chance and risk failure. 'Safe' for Abraham would have meant continuing in the pagan tradition of his father's household. For the daughters of Zelophehad, not rocking the boat would have allowed prevailing practice to militate against their right of inheritance. For the prophets of Israel, consensus meant capitulating to the polytheistic practices of their day. And for the rabbinic sages, the path of least resistance was to surrender in the face of the Temple's destruction. Playing in the "majors" involves risk, disruptive leadership, and more than a few mistakes. This was as true for the Maccabees as it is for today's Women of the Wall.
The midrash (Numbers Rabbah) relates a well known story that when the Jewish people left Egypt they found themselves at the shores of the Red Sea paralyzed by argument as to which tribe would have the honor of crossing into the sea first. With the Egyptians in hot pursuit, only one man, Nahshon ben Aminadav, took it upon himself to risk both the wrath of his coreligionists and death by drowning (the ultimate failure). Undaunted, Nahshon waded into the waters all the way up to his neck. Then, and only then, according to the rabbinic sages, the waters of the sea split open allowing the Israelites to cross over and escape to safety.
The example of Nahshon makes it abundantly clear that bold decision-making - the kind of decision-making that has transformative powers - is incongruous with reticence and a fear of failure. If playing in the little leagues is good enough, then, perhaps, there is no need to worry about failing. But if the big leagues are the goal then taking risks and making mistakes come with the territory.
The Torah underscores the fact that notwithstanding the desire, even the expectation, of success, all leaders fail on occasion. Indeed, missions are often not accomplished. Consider Moses, the quintessential Jewish leader, who, despite myriad accomplishments, did not fulfill his life's dream of leading the people into the Land of Israel. Who among us, however, would write off his exemplary career or dismiss his transformative leadership on that basis? The willingness to risk failure is a necessary precondition for great leadership.