How do you have a tough conversation?

Clarity for everything. Immediately say what it is about. Don't make it prettier than it is and be clear. Explain reason, cause, context, or problem. Prepare for it. You should be able to explain what you want in two to three sentences. Clarify and explain. Leave the other person room to respond and let off steam. Listen. Really listen. Look them in the eyes. Nod. Rephrase what the other says. Acknowledge pain or problem. Don't get comforting right away. Show understanding. Suggest an action. Connect an act, plan and follow-up to the conversation. And then live up to it.