Dealing with difficult conversations

I’ve written before about how online, text-based conversations can easily get tense, stressful, and often escalate into unpleasantness—Slack, Teams, and so on are great in some ways, and terrible in others. As I wrote then, I’ve found that “assume the best intent” is a valuable way of handling those exchanges (even though it has problems in other areas). But here are some other ways of dealing with these situations.

1. Learn some individual strategies

“Assume the best intent” is a general strategy for responding to comments you think are provocative. I’ve been amazed at how often my “obvious” negative interpretation of a comment is by far the only one when I ask someone else’s opinion.

But there are individual strategies for individual people, too. I knew one person who was aware he tended to respond very poorly to wordy questions—he would respond to minor elements of the question and miss the main point. That allowed me to use a strategy of keeping my questions short and direct. Unfortunately few people are both sufficiently self-aware and likely to offer such personal insights. In general, therefore, reflection is often useful for discovering such strategies.

2. Let it wash over you

Sometimes it’s just best to avoid the battle entirely. Occasionally someone says something I cannot make sense of, and cannot question without risking sounding provocative. Maybe someone says something for which the best interpretation still isn’t a happy one. In these cases I find it useful to just ignore the comment and return to another aspect of the conversation. Sometimes I’ll just step away with a neutral, “Okay, thanks, let me think about that.”

As we find ourselves approaching or inside a conflict situation there’s a natural urge to “win” or be “proven right” or “make our point”. But usually that is entirely different to the real purpose of the conversation, which is to find a productive outcome. So suppressing our strong, baser instincts results in a more positive long term outcome, at the cost of some short term secret personal pride.

3. Talk in person

I know a couple of people who have said, “If you can’t resolve it in three back-and-forth comments on Slack, then go straight to Zoom.” I’ve found this does require a bit of effort, because it’s so easy to get sucked into the text-based debate and keep typing (“I’m sure I can win them over with just one more well-crafted comment.”) But when I have stepped away and taken it to Zoom, it generally goes very well. I’ve seen others succeed there, too. People seem to be different and more understanding in a video call than in text.

4. Address it directly

There’s the conversation (our discussion) and there’s the meta-conversation (the way we’re discussing). Sometimes it’s possible and valuable to discuss directly with the other person how they thought the conversation become difficult, and what we might do differently. Ideally this will be a conversation that’s objective and driven by our genuine desire to work better together.

But it’s always a good idea to separate the conversation from the meta-conversation. If the other person is clearly wound up then questioning how they’re behaving in the heat of the conflict is extremely unlikely to go well. Instead, wait until things have calmed down before approaching them. I’ve found a polite approach is generally well received. The other times are when it’s too soon and the wounds are still raw.

So there we are—four ways of dealing with difficult text-based exchanges. I can’t say I never get drawn into such painful discussions, but I do know that these ideas for extracting oneself do work for me and for others.

Photo by Chris Fithall

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