You are the expert on the difficult conversations you have to have. I do have some thoughts on how you got there, how to avoid many difficult conversations, and how to get started with the next one that really is necessary.
Let's start with the difference between difficult conversations with people you have previously had great conversations with, and conversations that are difficult because you don't have shared experience of great conversations. Difficult conversations don't happen without history and context (generally this is what creates the difficulty). There are two kinds of things that matter about a shared past experience: the points of common good and the anchors to other conflicts. As you enter a difficult conversation, you have a choice about what part of the past you want to carry into the room.
This doesn't inevitably mean that finding shared experience of resourcefulness is a good way to go into a difficult conversation. But it is certainly worth checking in with yourself and discovering if there are resources in this particular relationship that would help you have this particular conversation. If there are (there usually are) then pay attention to those.
It's also useful to prepare for a difficult conversation by pre-handling the anchors to other conflicts. We've all had one of those conversations that included the phrases "you always" or "you never". These almost always lead to opening old wounds and fanning the embers of old arguments. Ask yourself: do I really need to go there? Does it help? Be careful how you answer. It often seems like focusing on the negative gives us the energy to make a necessary break. This may be true: it may also be an illusion. Anger is a rush and it can get things done. It can also leave a really ugly aftermath and fuel more difficult conversations.
The biggest edge that comes from examining your past shared experience before beginning a difficult conversation may be that you have a chance to observe the way your own emotions change and flow. You'll notice that good memories stir up one set of responses while a focus on past conflict prepares you for more conflict: your heart beats faster, your breathing gets shallow, and you can feel the adrenalin, even when you are just remembering. Remembering both resourceful times and past conflict gives you a chance to practice monitoring and adjusting your own state.
Practice. Think of a difficult conversation you need to have, and observe the changes in yourself as you think of it. Then let you mind go to shared experiences of strength or community. Notice that your state changes again. Now think of some of the past experiences that make you dread this difficult conversation, especially the ones that involve the other half of this conversation. Whenever you feel that your emotions are rising and your reason is slipping, simply go back to recalling shared neutral experiences (boring routine is great). Then work back to resourceful memories before returning to challenge yourself with memories that fuel anger or anxiety. Follow this pattern until you have sorted through what will help you and what may throw you off as you have this difficult conversation.
In future posts, I'll talk more about difficult conversations.