Every Negotiation Has Two Conversations

Positions are doors. Interests are the rooms behind them. Three questions to find out what's inside.

A founder speaks candidly with an adviser in a small business office.

Every negotiation has two conversations. The one you can hear — and the one underneath it that no one says out loud.

Today I want to give you something practical. Because this isn't just a concept. It's something you can use this week.

Here's the pattern.

Someone comes to you with an ask. A clear one. A specific one. They want a lower price. A later deadline. A different scope. A concession on something that seems straightforward.

You respond to the ask. You negotiate the thing they put on the table.

And later — days, weeks, sometimes months — it falls apart. Not because the agreement was wrong. Because it solved the wrong problem.

This happens everywhere. Not just in business.

A teenager asks for more screen time. What they're actually saying: I need something I'm not getting from the people in this house.

A colleague resists a new process. What they're actually saying: I'm afraid this change will make me irrelevant.

A partner says "it's fine." What they're actually saying: I've stopped believing this conversation will go anywhere useful.

Positions are doors. Interests are the rooms behind them. And most people spend the entire conversation knocking on the door — louder, more insistently — without ever asking what's inside.

Here are three questions that I've found can be helpful:

1. "What does this need to look like for you?"

Not: what do you want? That gets you the headline.

This question asks about the shape of the solution — and the answer almost always reveals the real need underneath.

2. "What are you most concerned about?"

Simple. And almost nobody asks it. Because we're so busy preparing our response to their position that we forget to find out what's actually driving it.

The answer to this question has rerouted more conversations than I can count.

3. "If we solve this part, does it change how you feel about the rest?"

This is a test question. It tells you whether you're working on the right problem. If the answer is no — if solving the stated issue doesn't change the temperature in the room — then the stated issue was never the real one.

Many of us learn this the hard way.

We invest weeks negotiating a contract renewal. The other side keeps pushing on price. We keep pushing back. We go back and forth. We pull out every tool we have.

We get the deal done. Price exactly where we thought it should be.

Within six months, the relationship is gone.

Because the price was never the issue. The issue was that they didn't feel heard. They'd been trying to tell us something — about the way the service was being delivered, about the calls that weren't being returned, about the feeling of being taken for granted — and we'd treated every signal as a price negotiation.

We won the number. We lost the client.

That experience taught me something I've never forgotten: if you just solve what's said, you can miss what matters.

A question to sit with

Think about a conversation that stalled recently. At work. At home. Anywhere the temperature dropped and the progress stopped.

What was the stated ask?

Now ask yourself: what were they actually worried about?

Those are usually different things. And the distance between them is where most conversations go wrong — and where the best ones find their way.

If this changed how you're thinking about a conversation you're in right now, reply and tell me. I read every one.

And if someone you know is stuck in a negotiation that isn't moving — forward this to them. Sometimes the problem isn't the deal. It's the question nobody thought to ask.

— Howard

First published July 3, 2026 in True North, Howard's weekly newsletter. Read it on Substack.

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