I find that difficult conversations are always easier when solutions are presented at the same time. Even if it's just advising of a tiny step that can be taken toward getting the outcome we want, I always try to deliver a "and here's what we are going to do about it" when I share difficult news with a client. This shows the client that I care about getting them their result and that because they are important to me I've given careful consideration to how we can keep things moving forward.