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Ask HN: Learning to Have Tough Conversations

13 points by vkurjsnnw ↗ HN
I think I’m generally a good conversationalist and speaker, but I’m terrible when it comes to really tough conversations both professionally and in personal life. I’ve always struggled terribly to break off unhealthy relationships or tell employees that they need to get their act together. Whenever I have to do have a tough conversation like that, I end up wanting to downplay things and finish the conversation more positively.

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?

13 comments

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eimrine
Try going outdoor and convince a stranger to borrow you $100. If somebody really borrowed you something then convince him that you return only half.
FractalHQ
I could never do this. It seems dishonest and unkind!
moviewise
I hope this article helps:

"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...

rawgabbit
Write down what you plan to say. Review the draft with your HR and peers for feedback. At the meeting, read what is written down and nothing else. End the meeting.

In general, you want to criticize the BEHAVIOR; do not criticize the person. Usually the conversation is like this: <your company> believes <rule> is nonnegotiable. This rule was broken when <details here>. If you continue to break <rule>, you are forcing me to take further action. To stress how important this is, I want you to take the rest of the day off. In the morning, I want you to sign and acknowledge that you have understood what we discussed today.

codingdave
I would feel quite insulted if someone told me to take time off to think about things and then sign an acknowledgment. Seriously, that is how teachers treated us when we were 8 years old. If you are in a position where you need to hand down non-negotiable rules, then just do it and leave it at that. End your discussion after, "If you continue to break the rules, there will be consequences."
rawgabbit
If someone broke a nonnegotiable rule, their feelings is of lesser importance than a document trail in case a lawsuit is filed.
codingdave
Documentation that a meeting was held is sufficient for an audit trail.
rahimnathwani
"Yes, we met on that day, but you never told me XYZ!"
codingdave
That is why you document the meeting. Record minutes. And save them. Don't require signatures of attendees, and definitely don't say "Go home and think about this." Signed acknowledgments is not how documentation works in governance processes. Meeting minutes and documented decisions are.
rahimnathwani
What you're describing now is more than "Documentation that a meeting was held".
ivank
It sounds like you are a people-pleaser. This is a common problem that I shared. The thing to learn is to have, state, and enforce boundaries. Otherwise some people pick up on a lack of boundaries and will do what they wish with you.

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).

https://youtu.be/tUOvY6Lfm1A

https://youtu.be/NqAJrWFzLp8

yrui
Some good books to get started:

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.

slano_ls
I can give an anecdotal answer to this. One thing I despise is pushing people into "boxes" but for this answer I will have to do that. My older brother and I throughout our lives have always gotten into many fights (as children do) and one thing that I noticed as that he never apologizes, and never feels bad for me after our fight is over. I on the other hand immediately feel horrible, and apologize immediately. Similarly this has translated throughout much of my life. Whenever it comes to having tough conversations, by brother would always be able to and not feel sympathy and in the end get what he wants. Me on the other hand, always ends up compromising for the goal of the other person being happy.

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.