What about being a shepherd implies contempt for people?  Did Jesus have contempt for his flock?  Do pastors show utter contempt for their congregation when they use the exact same metaphor?

No way that humility is the most important quality in a leader.  Was Patton humble?  MacArthur?  Chruchill?  Who was teaching these leadership development courses? 

Also, I'm surprised to hear a conservative would say that this is "a nation founded on the principle that everyone is an equal"-- the true principle, of course, is that all people are created equal and are afforded equal opportunity under the law.  As conservatives love to point out, there is no principle of equal outcomes.  You'd be pointing this out, I'm sure, if the context were different.