One of the hardest and most delicate tasks in the pastoral ministry is what I call the "pastoral dance." It's the subtle balance you have to achieve between being encouraging and affirming on the one hand, and trying to be strict in the values you hold up on the other. It's easy to retreat into one of the simple extremes, to be the legalist on the one hand or the "whateverist" on the other, but to maintain a balance between the two is terribly hard. Here's two illustrations, one from my own life and another from someone else's (thank God.)
Signing bulletins for children is one of those random little Sunday rituals. Kids often need a signed bulletin to prove to their religious education program that they attended Sunday Mass. This is especially true if they attend classes in one parish and worship on Sunday in another. I don't sign automatically, though. I demand an account from the kid. If they are preparing for a sacrament I ask them why they want it and what they think it means. If they are between sacramental preparations, I ask to know what they are learning. If they can't tell me anything--in the worst cases they don't even know if they are preparing for a sacrament or not--I refuse to sign. I tell them that it's ordinary wisdom not to put your signature on something if someone can't tell you what it is. However, I almost always sign in the end, and I do the whole script in a lighthearted way, so as not to embarrass the kid's poor mother who has diligently brought the kid to church. That's the pastoral dance. You have to affirm and encourage on the one hand, but you have to make sure the value is held up on the other, to avoid the great scourge of the "spirit of whatever."
To take a hypothetical and more difficult example, what would I do if I were the pastor of the new First Catholic, vice-president elect Joe Biden? I understand that he attends Sunday Mass diligently, so I presume I would be able to ask him for an appointment. But what would I say? How would I affirm and encourage him in his apparent effort to lead a Catholic family, but still explain that his unwillingness to defend the rights of the unborn is unacceptable? How does the public and notorious element play into it? Would there be a pastoral strategy to affirm what's good, like Sunday Mass attendance and being a Catholic family, while still making it clear that the notorious failure to use public influence is intolerable? If this were me, this question would be pretty heavy on my conscience.
The pastoral dance is hard. But you have to do it if you don't want to be the scribe that binds up heavy burdens on the one hand, or the person who casts their pearls before swine on the other.