In my personal and professional life I have to have difficult conversations from time to time; most people do. Avoidance and denial often get in the way of seeing through the conversation to a good outcome, and yet in my better moments I have managed, following the example of various role models in my life.
A long-since retired colleague, Jim Drummond, shared with me a checklist for such conversations many years ago. I lost it, of course, but have seen variations of it on the web. If you Google "Difficult Conversations Checklist" you can find various revisions. Feel free to try https://www.thefbcg.com/wp-content/uploads/2021/06/A-Difficult-Conversation-Checklist_Handout.pdf.
One component of the checklist is a systematic approach to empathy: what is the other person's narrative? Without some understanding of that, there is no good outcome that I can see. Sometimes it requires a series of conversations to achieve that; sometimes it's there immediately in an angry email.
Another component is perspective: aside from you and the other person, what would a neutral party make of both your stories? How would their narrative differ from yours?
Some understanding of these three narratives is key to separating objective from subjective. The other key is to articulate the emotions at play rather than pretend that they have no role in moving forward.
When I go into a difficult conversation, I spend most of my time on trying to decide how I will measure the outcome of the discussion. I find there's nothing worse than just going through some emotional turmoil without coming through the other side feeling that I have achieved something. If I can't find some criterion for success then probably the conversation is not going to be worth the cost.
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