How to Navigate 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 and not face-to-face.

A few pointers given here if followed can make such writing concise, clear, and insightful.

Tough conversations don't have to be so stressful.

Opening the conversation

Start by showing empathy while being direct about what’s going on. Without tiptoeing 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 harder.

For example:

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

It can also help to make clear at the outset that you’re trying to advance the conversation toward some kind of resolution, as in the following two examples.

Politely disagreeing: I appreciate your suggestion, but I think we need a different solution. (Next, kindly provide specific reasons and alternatives.)

Understanding mistakes or failures: We received some tough feedback from the client, and we want to better understand what went wrong and how we can do better.

Plan a few steps ahead

Try to think through how the person you’re writing to will react, then prepare accordingly. What information will they want? What next steps can they anticipate?

Incorporating such details into your draft shows you’ve considered their perspective—and it can provide a useful way to move past the uneasy news or awkward request you had to deliver higher up.

That said, if you find your contingencies approaching a level of complexity better suited to a flowchart, perhaps just keep things short and open-ended, then see which way the recipient steers the conversation.

Be polite; don’t hedge

It’s tempting to soften uncomfortable particulars by hedging with squishy modifiers. Usually, it’s better to be straightforward with the facts, as your recipient won’t appreciate you obscuring them behind vague language.

Hedging: Your ears may differ, but I’m not certain the audio quality of this recording is quite up to par for our podcast.

Direct: Unfortunately, the person speaking sounds too far from the mic, and I also hear a dog barking in the background, so we should re-record this segment.

When hedging stems from uncertainty, it’s often wise to be direct about what you don’t know and formulate it as a question:

Asking: Is it worth trying to re-record so we can get them closer to the mic and cut out some background noise?

Show you understand

It is believed that a good writer shows and doesn’t just tell. And that people appreciate feeling understood, especially amid tough conversations. So as your back-and-forth progresses, paraphrase the key points and concrete to-dos so it’s clear you’re reading closely, understand, and care.

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