Negotiating

I’ve never written about negotiating before.

It’s strange to me how the cues, emotions, and talk tracks are always analyzed from just one perspective—like a high schooler dissecting a frog in a 10th-grade biology lab.

It’s not that the information is inaccurate, but it often presents the dynamic as you (the human) vs. them (the adversary—aka the robot).

I say "robot" because every book and blog I’ve read on negotiating treats the other party like a predictable machine.

As if they’re not going to be executing their own games and strategies.

They assume your adversary will never read their book. But what if they do?

I’d pay good money to see two negotiators armed with the same blueprint go head-to-head. Would they cancel each other out? Would they malfunction like two automated customer service reps caught in a loop?

With all my frustration about how the art of negotiating is discussed, why am I writing about it now?

Because it’s been one of those weeks—the kind where I’ve heard more “no’s” than “yes’s” and been ghosted by people who had promised me otherwise.

Sure, that’s just business. Most days, I’d shrug it off. But today? Today, it feels different.

I feel confused—maybe even betrayed. Actually, no maybe about it. I feel betrayed.

Why would someone casually say they’re ready to sign, ask for the contract, text me that they’ll review it shortly—and then disappear?

If this were a one-time thing, I wouldn’t be writing about it. But it happened five times in one day.

I want to of course vent about it (see above), but I feel compelled to share what I know about negotiating.

I know it seems counterintuitive to do this after a string of Ls, but in my eyes, it’s the perfect time.

The ultimate test to doubt everything I know or keep going. I realized that it’s a moment where I’m not going to change course.

I’m going to weather the storm, while still making adjustments to my boat.

Because no matter how I dress it up, the no’s are my fault. And as a result, I have to make some adjustments.

And despite the losses this week, I know this: my negotiation methods have worked more times than they haven’t.

I guess you’ll have to take my word for it, but here are my thoughts on how to approach negotiating, regardless of your craft or industry.

To state the obvious, you still might fall flat, but I can tell you that without this foundation, you don’t stand a chance.

1. Build the Profile (Fast)

Before you try to convince someone, you need to understand them.

In the first minute, construct a clear mental picture:

• What do they watch on TV?

• What do they drink?

• What do they do on weekends?

Why does this matter? Because negotiation is about relatability. When you understand their world, you naturally start speaking their language. You become an ally—not just another salesperson, recruiter, or dealmaker.

2. Extract Their True Pain Points

Most people don’t just tell you their real problems—you have to listen for the gaps in their story.

• Notice hesitations in speech.

• Spot inconsistencies.

• Pay attention to what they don’t say.

This doesn’t mean assuming they’re lying—but it does mean recognizing that people often tell themselves fairy tales. Your job is to gently but persistently separate fact from fiction.

3. Identify the Logistical Layups

Some deals don’t happen because they can’t happen.

If their budget is $1,000 and your product is $5,000, it’s not about negotiation skills—it’s a math problem.

Before wasting time, confirm that:
✅ Their organization can actually implement your solution.
✅ The financials make some level of sense.
✅ The decision-makers are actually involved.

4. Master the Game of Status

Once you clear the logistics, the real game begins.

The key? Don’t position yourself too high or too low.

• Too high, and you intimidate them.

• Too low, and they don’t take you seriously.

The sweet spot: respected as an expert, while respecting their experience.

5. Use the Dream Scenario

Instead of asking vague questions, try this:

“If you could have the perfect solution, what would that look like?”

There’s no reason for them to lie here—it’s hypothetical. And once they lay out their dream scenario, you can:

• See what’s realistic and what’s just fluff.

• Gauge their true priorities.

• Identify what they’re secretly testing you on.

6. Deploy the Power of Hypotheticals

Hypothetical scenarios remove pressure from the conversation.

People let their guard down when discussing "what-ifs" because they don’t feel committed to their answers.

• “Let’s say you could wave a magic wand—what’s the first thing you’d change?”

• “If I could remove that risk entirely, would we be in business?”

These questions allow you to explore possibilities without triggering defenses.