I’ve read lots of general advice on this and know that dragging/downplaying things is usually worse for the receiver as well, but I haven’t been able to get better.
How do I learn to have tough conversations?
"The next time you find yourself embroiled in an argument with someone that’s contentious and uncomfortable, say, institute the following rule: you don’t get to respond to the person’s claims until they’ve exhausted that particular claim and […] until you have recapitulated their viewpoint and summarized it in a manner they find acceptable."
https://moviewise.substack.com/p/communication-insights-from...
Difficult Conversations by Stone, Patton and Heen
Crucial Conversaions by Patterson et al.
Difficult Conversations is about why difficult conversations are difficult. It's based on research done in the Harvard Negotiation project.
Crucial Conversations is an approach where you learn to recognize early when conversations become difficult, and teaches some techniques to use when they do.
Something that may help is to recognize that you are allowed to disappoint someone. You are not the sole cause of a situation. In a problematic situation, sometimes the best we can do is to have boundaries and see whether people want to adjust their behavior or leave. Simply having articulated boundaries will often cause people to be less bothersome (with you, anyway).
In general, you want to criticize the BEHAVIOR; do not criticize the person.
Usually the conversation is like this:
Throughout my life the thing that I have learned, is that you have to be able to either feel that the thing you are saying will help the other person hence the need for no sympathy, or embrace the fact that you are difficult at being unsympathetic and cultivate an environment around you that appreciates sympathy, but also understands the requirement for understanding.