When and how to break the news?

I pride myself on being a good if not great negotiator, however sometimes and it is inevitable....we are less than successful. This is when those whom have entrusted in you to "Get the job done" even when the job is a hole they themselves have dug must be informed that the plan just did not work out and they must suffer the consequences of whatever hole created however grand. There is one thing, however; when I believe that someone have been wronged or tricked into digging that hole and that person is inherently a "Good" person. I feel bad and have lost my ability to break the bad news. I'm not sure if I'm loosing my touch or its just that now that money isn't the issue I care more for victims of the legal system. Whatever the case is, I guess the answer to my question is, "As soon as possible and to the point.". Now lets see if I can practice what I preach, that is a true test.