The conversation you're avoiding

Avoiding an unpleasant conversation has one obvious cost: the problem stays. Then it compounds. We keep ruminating until the thing grows into an enormous ball, seasoned with all our presumptions about the other person, which are almost always wrong. And one day it comes out anyway, at the worst moment and in the worst tone, so the attempt to protect the relationship achieves exactly the opposite.

A workshop two of us took on difficult conversations left a method worth writing down. Its premises first, because they do most of the work. We do not have the truth: we do not know what is actually in the other person's head. Most of the time, people act with positive intent. And most of the damage was done without the other person even noticing they caused it.

Second premise, the one that unlocks the rest: kindness and honesty are not a trade-off. It often feels like being kind means not being fully honest, and vice versa. But there are a thousand ways to say the same thing, and at least one of them combines both.

The method itself is short. Before anything, strip the facts of the story you have built around them, alone or with someone you trust: what actually happened, minus the emotional charge and the decorations. Then the conversation: the facts as objectively as you can state them, how they landed on you, and your own share of responsibility, offered by you rather than extracted from you. In person if possible; for a remote team like ours, a video call with everyone involved. Close by naming what each side takes away, and put a follow-up in the calendar ten or fifteen days out, because the goal was never to feel better once. It was to change something.

Start small if you want to test it: some pending, low-stakes discomfort, the laundry-on-the-chair tier of conversation, before the ones that carry real weight. It is striking, once you try it, how much of the dread lived in the story and how little in the facts.

First published in our internal knowledgebase in January 2024. Adapted for the blog.