Jesus was brutal on leaders while being compassionate with the crowds. He saw leaders as blind leaders of the blind; so, He saw them all as blind but blamed the leaders for the blindness, not the crowds. He invested revelation in a rather small group of leaders with a strategy to alter the situation by changing the leadership.
Jesus is the Good Shepherd. His discussion of sheep is really more about leadership than about the crowds. He discusses the quality of leadership that represent good shepherding. He has compassion on the crowds, seeing them as “sheep with out shepherds.”
Yet, He intentions are not that people should remain sheep. Certainly there are people in the kingdom who are sheep and will remain sheepish. There are people who should be treated as sheep. However, Jesus never presents the kingdom in terms that leave us thinking that this is the only picture of kingdom we should have. The metaphor isn’t pervasive.
Jesus certainly intended His apostles to have some shepherding skills and function as shepherds. Some of them, at least. He tells Simon to “feed His lambs” and “feed His sheep.” Simon Peter is an apostle with shepherd functions. Barnabas is an Evangel with shepherd functions.
But the expansion of the kingdom comes when more and more leaders are prepared and positioned to produce, when the crowds of sheep are cared for but leaders are identified, trained, prepared, and positioned. The kingdom has leadership assignment and leaders are the mark of its maturity.