In the gospels, Jesus spends a lot of time with the Pharisees. The Pharisees are the religious denomination within Judaism that spends the most amount of time, energy, and effort seeking to understand and apply the law. For the most part, despite how the Pharisees are presented in the gospels, their intent was good. They recognized the law as given by God for their own good and that the highest goal of one's life was to conform to the law. In doing so, one would conform to God's vision for them and their people.
But sadly, as good intentions sometimes go, their desire to see others conform to the law led them to methods of control where they would exhibit a lack of compassion for others. This is why Jesus was often in conflict with the Pharisees. He preached and focused on God's grace and went to those most in need of God's grace. These were the very people the Pharisees likely would have ignored in favor of "fine-tuning" those who were already "close" to the ideal.
The Pharisees, then, as well as the chief priests, the scribes, and the elders--those whose responsibility was teaching and leading the people to knowledge of God--failed as shepherds. The main reason for their failure, at least according to how Jesus presents it in Luke, is due to their failure to work with those most needing their help. Instead, they often served themselves by keeping to their groups where they could tightly control behavior (Luke 14:12-14).
Therefore, in a context of discipleship (Luke 14:25-34), where Jesus spells out the criteria of discipleship--carrying a cross, counting the cost, and preserving faith through action--he teaches three parables that describe what true shepherding is (Luke 15).
The three parables in Luke 15 are against the Pharisees. The problem is highlighted at the beginning of the chapter when, in response to those who were gathering to hear Jesus teach (tax collectors and sinners), the Pharisees grumbled that Jesus "welcomes sinners and eats with them" (15:2). The problem, as they perceived it, was that Jesus associated with the wrong people. So Jesus tries to correct their view--and teach them that they need to shepherd those who most need shepherding--by telling three parables that revolve around the idea that it is a bigger deal in heaven when one sinner repents than when ninety-nine self-righteous people sit around and compare notes (15:7, 10, 32).
The first parable teaches that good shepherds take risks to shepherd those most in need. The shepherd who lost one sheep left the other ninety-nine by themselves and went off in search of the one. He took a financial risk in doing so, but the one was precious enough for him to do so. Here, the Pharisees are indicted--they would leave the one who wandered away for the sake of "protecting" the ninety-nine left behind. After all, they can't be responsible for every person who won't accept their teaching.
This attitude has been a long-standing problem in the Judeo-Christian heritage. Because we tend to be more comfortable around people who are most like us, we can unintentionally neglect others who need help. In worse cases, we look down on people who are not like us, those who need real, spiritual help. We blame them for their condition instead of looking to serve them.
For example, suppose a church member struggles with some aspect of the church, or some person within the church, and decides to quit the church. Many people, tragically, would write that person off, perhaps even criticizing them. A good shepherd will risk all to go visit that person, serve them, and try to bring them back even though he may be criticized himself for reaching out to someone who is looked down upon.
In the second parable, Jesus teaches that good shepherds care enough about people to spend energy focusing on just one person. His parable is about a woman who has ten silver coins but loses one. Rather than viewing herself as still being ahead with nine, she lights a lamp, sweeps the house, and searches carefully until she finds it--then throws a party over finding one coin! Again, the Pharisees are indicted--they would rather focus on the nine remaining and the let the one go.
But good shepherds go after one missing person. They know what they have in the first place so they know when one goes missing. And they do not write off the one that goes missing; they spend their time, energy, and effort to find that lost one.
In the third parable, Jesus teaches that good shepherds care more for the needs of those who need help than the selfish whims of those seeking to be served. The parable of the "lost son" (or the "older brother" or the "loving father") is perhaps the hardest-hitting parable of the three. This parable indicts the Pharisees in a way the other two didn't. In this parable, a son who once was a "good son" leaves home and squanders his inheritance, only to return home empty-handed. The older brother must have been pleased to see his brother slinking back onto the family estate. But his joy turned to anger when he saw his father run out to greet the lost son! Later, his father rebukes him for not celebrating the return of his brother, who had wandered off.
Good shepherds are not concerned with the selfish whims of people who are in the game for themselves. Sometimes, churches can become made up of selfish members who organize the church around their needs and desires. When someone creates a program to reach out to a different (i.e., "wrong") people-group, especially if that means changes for them, these people become angry and complain. The Pharisees did not like how Jesus associated with the "wrong" type of people when he should have been supporting them.
These three ideas about shepherding coalesce around one main point: good shepherds are relationally focused on the spiritual growth of others. This plays out in two different ways in Luke 15. First, Jesus teaches that it is always proper and appropriate to shepherd those most in need of shepherding. For him, that was the "tax collectors and sinners," those members of the community that most needed to hear the message of the kingdom of God. At other times, it was sick and lame people who needed attention from Jesus, more "undesirables" that were overlooked by society. In our situation, it might be poor people that we reach out to, without judging them for "not being wise with their money." It could prisoners that are reached out to, without regard for what they did in the past.
Second, Jesus teaches that it is always wrong and inappropriate to ignore and write off people who don't act the way we think they should. This was his message to the Pharisees, seen most clearly in his comments about the "older brother." Let's be clear--we do not shepherd anyone if we have no contact with them, if we leave them to fend for themselves and continue to wander away. Instead, we need to overcome our differences, our own sense of the rules and what's right, and perhaps even our own prejudices, and reach out to those in need. This is what good shepherding is.
Again, we can look around us and see this type of shepherding in action. It may not be prominent, but it's there. As you look for spiritual leaders, look for those who meet these criteria for shepherding. You'll know a good shepherd when you see one.