If today's LinkedIn post landed anywhere for you, you're now sitting with a specific conversation and a slightly uncomfortable realisation: you've been preparing to speak into a room you haven't yet seen.
I want to walk through what to do about that.
Why we default to speaking-first (and why it doesn't work)
Almost every model we've been given for difficult conversations puts speaking at the centre. How to open. What to say. How to phrase it. How to be assertive without being aggressive, honest without being brutal, clear without being cold. The whole architecture of communication training is built around the moment you deliver the message.
But if you look at what actually happens in the difficult conversations that go well, the pattern is different. The person opening the conversation almost never leads with what they came to say. They lead by discovering where the other person actually is.
There's a specific reason for this. Any message you've prepared has been built inside your own frame: what you think is happening, what you believe about the situation, what you assume the other person understands. Almost all of that is guesswork. Some of it will be right. A meaningful amount of it will be wrong and you have no way of knowing which is which until you find out what the other person has been carrying.
When you speak first, you're doing something specific, you're forcing them to receive your version of reality before they've shared theirs. Even when your version is accurate, this creates a specific problem: they now have to react to your frame instead of contributing their own. The conversation becomes a negotiation between your interpretation and their defence of themselves within it. Which is not the conversation you actually needed to have.
What the listening-first opening actually looks like
The alternative isn't asking a vague question and hoping something useful comes back. It's a specific structured move.
Step one: signal what you'd like to talk about, but not your conclusions about it.
The opening isn't a statement. It's an invitation to explore something together. Instead of "I want to talk about how you've been handling the project," the opening is "I've been thinking about the project, and I'd like to talk it through with you." The first opens with your conclusion. The second opens with the territory.
Step two: ask what they've been noticing before you share what you've been noticing.
This is the counterintuitive move. You have things to say. You've been carrying them for weeks. But the discipline is to hold them, briefly, while you find out what the other person has been carrying about the same situation.
The specific question is not "what do you think?", that's too abstract and often produces a defensive answer. The specific questions are things like:
"What's it been like from your side?"
"How have you been reading the last few weeks?"
"What do you think has been going on?"
These are all open enough that the other person can shape the conversation, and specific enough that they're not fishing.
Step three: listen for what you didn't know.
Almost always, the person will say something you didn't expect. A frame you hadn't considered. A concern you hadn't seen. An interpretation of your own behaviour that you weren't aware they were carrying. The temptation is to correct or defend. The move is to notice it and let it land.
Step four: only now, share what you came to say, adjusted for what you've just learned.
You still get to say what you came to say. But now you're saying it into a room you actually understand. Your language will shift. Your emphasis will change. Some of what you were going to say will no longer make sense. Some of it will make more sense than ever, and you'll be able to say it in a way the other person can actually hear.
The whole conversation is now a different conversation. Because you started by finding out where they were, rather than delivering where you'd already decided to go.
This is the work my upcoming book is built around
Almost every difficult conversation people carry, whether with partners, colleagues, family members, clients, collaborators, has been prepared with the wrong opening. We spend hours drafting what we're going to say into rooms we haven't yet understood. And then we're surprised when it doesn't land.
My forthcoming book, The Zero-Sum Illusion (out September 2026), is a practical toolkit for exactly this kind of work: the frame shifts, opening moves, and structured practices that turn the conversations we've been carrying into conversations that actually change something.
The listening-first opening is one of the core moves in the book, and the framework goes significantly deeper than I can share here: into how to listen without collapsing your own position, how to hold your view while genuinely absorbing theirs, and how to know when the listening phase should end and the sharing phase begin.
Pre-orders open in August. I'll send the link the moment they're live. Until then, try the four steps this week and tell me what happened.
I read every reply.
- Grant