Strong negotiations hinge less on numbers and more on understanding the person across the table.
How understanding people improves negotiation outcomes
Most negotiations don’t fail because of bad math.
They fail because someone misunderstood the person sitting on the other side of the table.
Early in my career, I believed preparation meant spreadsheets, scenarios, and fallback options. That matters. But it’s only half the work. The real leverage often comes from something simpler and harder at the same time: knowing who you’re dealing with.
Once you answer that question clearly, the negotiation changes shape.
The First Mistake: Treating Negotiation as a Transaction
Many people walk into negotiations thinking they’re trading numbers. Price for volume. Time for money. Risk for return.
That’s the surface. Underneath it, every negotiation is personal.
I’ve seen deals collapse over terms that were financially irrelevant. I’ve also seen weak offers accepted because the other side felt understood.
The difference wasn’t intelligence. It was attention.
People Don’t Decide the Same Way
Some people optimize for safety. Others chase upside. Some care deeply about optics. Others want speed and silence.
If you assume everyone thinks like you, you’ll miss this completely.
As a CFO, I once negotiated a vendor contract where price was clearly not the issue. The supplier kept pushing back, even though the numbers worked in their favor.
It turned out they were worried about internal approval. They needed a structure that made them look disciplined to their board.
Once we reframed the deal to support that story, it closed quickly.
Three Questions That Matter More Than Price
Before I negotiate now, I try to answer three questions about the other person.
1. What Are They Measured On?
Compensation plans quietly drive behavior.
A sales lead paid on revenue will push volume. One paid on margin will stall. A manager judged on cost control will resist anything that looks flexible, even if it’s smart.
You don’t need to guess. Listen to how they speak. What do they repeat? What do they avoid committing to?
Follow the incentives. They explain more than words.
2. What Risk Do They Personally Carry?
Risk isn’t abstract. It’s personal.
Is this person signing their name? Are they new in the role? Are they cleaning up someone else’s mess?
People with personal exposure behave differently. They need cover. They need time. Or they need certainty.
Ignoring that creates friction you can’t price away.
3. What Do They Need After This Deal?
Every negotiation sits inside a longer story.
Maybe they need a win to regain credibility. Maybe they need stability before a fundraise. Maybe they’re preparing for an exit.
If your proposal helps them with what comes next, resistance drops fast.
If it blocks them, expect delays, even if the deal looks good on paper.
Listening Is a Competitive Advantage
This part sounds obvious. It rarely happens.
Most people listen just long enough to respond. That’s not listening. That’s waiting.
Real listening shows up in small ways. Silence after a key question. Letting an awkward pause sit. Asking a follow-up that wasn’t on your list.
Some of the best information I’ve gotten in negotiations came after I stopped talking.
Signals Are Everywhere
People tell you who they are without meaning to.
- How fast they reply.
- Who joins the call.
- What they send in writing versus what they say verbally.
These details reveal decision style, authority, and comfort level.
If someone avoids putting things in email, they’re protecting optionality. If they copy three people on every message, they’re building consensus—or cover.
None of this is random.
Adjusting Without Being Obvious
Knowing the other person doesn’t mean manipulating them.
It means framing the same truth in a way they can accept.
I don’t change the economics of a deal lightly. I change the presentation all the time.
For analytical counterparts, I lead with structure and data. For operators, I lead with execution and timelines. For founders, I lead with control and upside.
The offer stays the same. The doorway changes.
When Negotiations Go Sideways
If a negotiation stalls, it’s usually not about the last term discussed.
Something earlier didn’t land.
When this happens, I stop pushing and step back. I ask a simple question: “What’s the part that’s hardest to get comfortable with?”
The answer is rarely what’s on the term sheet.
Sometimes it’s fear. Sometimes it’s pride. Sometimes it’s a bad experience they had years ago with someone else.
You don’t fix that with pressure.
A Note on Walking Away
Understanding the other side doesn’t mean forcing a deal.
Sometimes knowing the person tells you this will never work.
That’s still a win.
The fastest way to lose leverage is staying in a negotiation that doesn’t fit. Time and attention are finite. Spend them where alignment is possible.
The Quiet Edge
The best negotiators I know aren’t aggressive. They’re observant.
They speak less than expected. They ask better questions. They rarely rush.
They understand that numbers convince spreadsheets, but people convince people.
Once you truly know who you’re negotiating with, outcomes improve in ways that feel almost unfair.
Almost.
Book Recommendation
“You Can Negotiate Anything” by Herb Cohen is often overlooked. It’s practical, human, and grounded in real behavior, not theory.
Your Turn
What’s one signal you’ve learned to watch for before a negotiation starts?
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