The academic and discipline problems that advisees encounter can be opportunities for them to get to what's really bothering them. Dreams may be the path to the unconscious, but I would add that academic and discipline problems can be part of that path as well. In your conversations with an advisee never overstate or understate a problem. Let the advisee create the agenda. The danger at one end of the spectrum will be to be seen as a psychological peeping Tom and at the other end as being indifferent or uncaring.
Some people love to hear gory details about the negative.
Others love only to hear that the sun is still shining and nothing could be wrong. Be aware of the topics that you like to discuss with advisees and those that you don't. It is human nature to direct the conversation to areas where we are comfortable and to avoid areas that make us uneasy. If there is something that you are uncomfortable talking about, make sure that you connect the advisee with someone that you believe wouldn't mind discussing the issue. Inconvenience yourself for your advisees, and they will do the same for you.