How to Deal With a Stressed Out User

I'm thinking about the tough love problem. What if this person actually just needs some tough love and someone to really say, look, you've got to get your app together? In the short term, this might sound actually a little hurtful of the person. But maybe it's good for the long term. At that point, what is even the right behavior? That seems like the harder version of the problem to me where there's ambiguity even as to what the model should be doing.