Any persuasion or intimidation check is a die roll, and should be. No matter how you're going about it. In the specific example, again, we're trying to subvert what she believes is the correct course of action. Since her intention was not to kill the thief, initially, we do have the potential to make it worse, and we should have that potential. I get people will feel bad about the outcome, I certainly did, but we made a decision to interject ourselves into their internal struggle, and I'm not even sure that's the right word, the better concept is we're interjecting ourselves, and our opinions, into something that is none of our business. Do we want to save the child? I certainly did, and I did, once out of two tries, so far, but it shouldn't be something where we spend a half hour in a dialog tree trying to find a way to manipulate the druid into changing their mind. How many hours of the dialog we're having now would it take to change your mind about what happens with this scenario? Will we both be holding the same position in a week? I would be, because I understand that I likely will not be able to change your mind, and I know it's possible that I won't change the druid's mind either. Not every dialog puzzle should be solvable by just cycling through choices until they relent, and, in fact, w/out a skill check to persuade them one way or another, why should we be able to convince her to not lock up someone that stole a holy relic from the temple?
In a PnP situation, where the dialog isn't scripted, a DM can roll a die check on every point raised by the players. In this instance, that's both impractical, and covered, by giving the player a chance to use dialog skills to manipulate the druid to our desired outcome. It could have just as easily had no way for us to influence it, given the nature of the druid in question. I don't know what happens if we just ignore that, and hammer her about needing a healer, and then leaving the dialog, and I'm not even sure it's possible, but if it is, is there another outcome? Could it be that, by sticking our nose where it doesn't belong, and failing that check, we are responsible for a death that may not have happened under any other circumstance? What happens if we say nothing, I seem to recall that that's an option? "You roll the dice and you take your chances" is an expression I've heard a lot. It's associated with gambling, I believe, but the sentiment remains the same.
