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Was Moses’ Failure Generational?

Recently I read The Biblical Story of Moses: Lessons in Leadership for Business by Paul J. Herskovitz and Esther E. Klein.  The authors posed an interesting idea:

“Moses’ failure of leadership is the result of his failure to take into account the differences between the two generations.”

They suggested that Moses did not enter the Promised Land because he did not know how to adapt to leading a new generation.

To prove their point, the authors quoted Nathaniel Helfgot with the following:

“Moses, by hitting (the rock) rather than speaking (to the rock), responds to this current crisis in precisely the same fashion as he had responded to the problems of the generation that had left Egypt thirty-eight years before. It was not the sin and its severity that caused Moses to lose the privilege of leadership. Moses’ “desert response” to this second water-crisis revealed that he was not a leader who could address the concerns and crises of a new generation, one which would enter the Land of Israel. It was clear that he was still tied to methods and perspectives of leadership which, though proper for the needs and concerns of the generation that left Egypt, were ineffective and inappropriate in the new situation.”

We need to work hard to understand the issues we are facing AND the people involved in those issues.

I wonder, which issues are we currently mishandling because we are more focused on the issue than the people involved in the issue?