What does it take to REALLY listen to a person? Not to just wait until it is your turn to speak, but to truly listen from a state of concern and desire. To listen from within their heart and mind and truly understand a situation from the other person's point of view.
In TMC, we call this looking at the "other side of the brick" If you were looking at one side of a brick you might see the long edge that is filled with holes, whereas another person might see it as a short solid side - each of us thinks we are looking at the same thing (the brick) although our perceptions can be quite different. We can both think "I am right" about this, and in actual fact we are both right about what we are seeing. The skill of being able to pick yourself up from what you know to be true and look at the brick from the other person's view really gives you an amazing skill of observation. This can allow you to truly understand their problem, issue etc and be honestly empathetic and sympathetic.
When you first begin to listen like this, there are moments of discomfort when you put down your own perception to hear another's. We do need to be willing to be a little uncomfortable to listen in this way initially, however the benefits of this listening far outweigh the initial awkwardness.
Be patient. Make this conversation more about them than about you. Be quiet and allow them the space in which to express. If you are going to share or speak or fill the silence, please do so with comments which will forward the conversation, not halt it or reverse it. This will begin you on a path towards some of the most amazing conversations you can have... and you will wonder why you had so much trouble understanding someone else in the past!