How to Negotiate Difficult Conversations in Writing

Some conversations just aren’t easy. 

Breaking bad news to someone, finding a respectful way to disagree, asking a favor, or reviewing a situation that didn’t go well—these are all hard things to do, perhaps especially when so many conversations now occur in writing, not face-to-face, due to the COVID 19 pandemic lockdowns.

Opening a conversation

You should start by showing empathy while also being direct about what’s going on. Resist the urge to tiptoe around the subject, make clear you’ve given thought to how it will land with the recipient, and that you want to avoid confusion or making things worse. For example: 

When giving bad news, say: I’m sorry to have to tell you this, but the repair process will be more extensive than we initially had hoped for.

NOTE: It can also help to make clear, right at the outset that you’re trying to advance the conversation toward some kind of amicable resolution.


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