Leadership is the art of motivating people to do what they would not otherwise be inclined to do. Axiomatically, Jewish leadership is almost an oxymoron. We are a stiff-necked people for good and for bad. Jews are not prone to bending their will and as a result, many a Jewish leader has had more than their fair share of heartache.
In the three parshiot dealing with Yosef, we have a most striking contrast between effective and ineffective leadership. Yehudah's natural leadership abilities are dramatically magnified by his brother Reuven's seeming ineptitude. Reuven's awkward attempts to provide leadership meet with limited success. Yehudah, however, is able to bend the will of his brothers, his father and even the viceroy of Egypt.
Great insight can be gained by comparing the way Reuven and Yehudah try to convince their father to allow them to return to Egypt with Binyamin. Yakov's indifference to Reuven's plea is easily understood, given the assurances Reuven gives his father. If Reuven's plan fails and Binyamin is lost, Yakov is given the right to inflict poetic justice (midah k'neged midah) on Reuven by killing his sons. It is hard to imagine why Reuven would believe that Yakov would be motivated by the thought of killing his own grandchildren. In contrast, Yehudah provides convincing arguments, personal responsiblity and appeal to the unity of the group he is trying to lead. Compared to Reuven, who speaks of my children vs. your children, Yehudah speaks about the survival of all three generations together. Knowing that Yakov cares greatly for his children and grandchildren, Yehudah points out that if permission is not granted to go to Egypt, the entire nation will die. Not only does Yehudah stress his personal responsibility to his father, he later lives up to it when Binyamin is arrested: Yehudah's immediate response is to offer himself up as a captive in place of the brother he has sworn to protect.
More than anything else, however, Yehudah is a master of timing. Reuven's idea of timing is to address a situation as soon as it arises. Yehudah knows that one must be patient, that silence is better than speaking to men unwilling to listen and consider alternatives. As soon as the brothers return from Egypt without Shimon, Reuven tries to convince Yakov to take the necessary risks and send them back with Binyamin. Yakov was certainly still in shock at the loss of Shimon, and certainly in no mood to be convinced into taking more risks. Yehudah, however, bides his time and waits for the famine to get more pressing - he knows to wait for his father to calm down and realize the questionablity of his own obstinacy. Later, in the midst of a discussion between Yakov and his sons that seems to be going nowhere, Yehudah senses his cue. The very futility of that discussion gives proof to Yehudah's assertion that the status quo is untenable. Yehudah knew that the most convincing proofs would not have worked until that point in time when Yakov was ready to listen.
Timing was also what allowed Yehudah to save Yosef from the pit in the first place. Whereas Reuven strikes an uneasy compromise with his brothers, Yehudah is able to get his brothers' full endorsement. Rashi marks the difference between the brothers' responses to Reuven and Yehudah, by noting that the brothers' "shmeeya" of Yehudah denotes acceptance, something absent from their earlier acquiescence to Reuven. As in the previous example, Yehudah is only able to convince his brothers once they calmed down and their guilt feelings started to seep in. The brothers had to be ready to listen.
While Ehud Barak's initial moves seemed impressive(see ideas 12), he is now showing that he lacks Yehudah's most powerful leadership tool - timing. Indeed, Barak mounted arguments that, like Yehudah, spoke of national unity and personal commitment. He distinguished himself from Rabin by showing sincere appreciation for the settlers. He avoided Rabin's unfortunate decision to villify his opponents on the right and instead sought to explain why his policies were for the benefit of all Israelis. So far, so good.
In August, Barak could have convinced a majority of Israelis to make great sarifices for the sake of peace. I believe that the further concessions now being discussed would have been doable (and even productive) several months ago. That was then. Yehudah would have realized that by now, the window of oppourtunity (or insanity for those of you on the right) has been shut. Barak himself articulated the gut reaction of most Israelis when under attack - no negotiations and no new concessions. Right or wrong (and I think it's right), we are not in a mood to be generous to people who resort to violence when they cannot get what they want. Our emotions are still frayed by the random killing and maiming of Jews endorsed by Palestinians across political lines. Right or wrong, we are not ready to listen. Like Yehudah would have, Barak should have realized that silence is better than trying to convince people at a time when they cannot listen. The timing has been lost and what is left is to wait for better opportunities in the future.
Perhaps Yehudah had the luxury of not having election deadlines, but ultimately it makes no difference. A true leader will always be able to save the day when the timing is right. When the timing is not right, a skilled leader bides his time. Otherwise he ends up becoming like Reuven: at best gaining resentful compromises and at worst becoming totally irrelevant.