our Twitter (X) feedView our Youtube channelView our Instagram feedView our Substack feedView our Spotify feed With the right preparation and follow-through, anyone can get better at having difficult conversations. Get curious, find purpose, and become more resilient at work Mind and BehaviorEmotional IntelligenceCommunicationDifficult Conversations Adapted from Unspeakable: The Taboo Topics We Avoid and How to Talk About Them by Christina Wing. Published by Harvard Business Review Press.
Copyright 2026 Harvard Business School Publishing Corporation. Make no mistake: Having a conversation around a topic we’ve been conditioned not to talk about is very much a skill. It’s coachable, and if you work at it, you’ll get better over time.
But to develop that skill, it can help to have a place to start. Here are eight practices you can borrow to make your next difficult conversation more successful. Use them often, and you’ll find your skills improving, too.
It’s important to know whether you’re trying to have a dialogue or a monologue. Are you seeking an agreement, a compromise, a collaborative solution — or are you simply presenting someone with an uncomfortable decision you’ve already made unilaterally? In other words, what is your goal?
For instance, if you’re breaking up with a partner or firing an employee who’s just not working out, those are difficult actions and involve uncomfortable conversations, but they’re not dialogues. Yes, you’ll listen politely to what the other person has to say, but the goal of this conversation is to make a clean break, not to have deep, two-way communication aimed at solving a problem. One of the worst things you can do is ambush someone with a hard conversation.
I’ve seen people try to sneak these in at the breakfast table (during the morning rush), on the way to the airport, or — God help us — over text. Randomly phoning someone or dropping into a colleague’s office unannounced to have a conversation about a controversial or long-buried topic suggests the discussion is casual and unimportant — the opposite of what you should convey here. Similarly, even when distance separates the people involved, I try to convince them not to have these conversations via videoconference.
Extract — continue reading at the source.
