Let’s get real.

If you’ve been in the game long enough, whether it's business, sales, management, whatever you’ve met them. The hard-nose. The cold stare. The zero-sum mindset. The negotiator who treats every deal like a high-noon shootout in a dusty Western town.

You know the type.

They walk in with a grin that doesn’t reach their eyes and a briefcase full of “no’s.” They’re not here to solve a problem, they’re here to win. And if you lose? Even better.

So, how do you deal with someone like that? How do you negotiate with the devil and come out with your dignity and your deal intact?

Glad you asked.

Let’s break it down. No fluff. No MBA jargon. Just straight talk, from someone who’s sat across more than one metaphorical gunfighter and lived to tell the tale.

The Two Types: Problem Solvers vs. Gunfighters

Before you whip out your contract and start slinging counteroffers, you’ve gotta ask yourself one critical question:

Is this a one-shot deal or an ongoing relationship?

That single question changes everything. We’ll explain why in a bit, but for now let’s look at the two types of negotiators.

1. The Problem Solver

These folks want to work with you. They see negotiation not as combat, but as collaboration. Their goal? Solve the issue, find the win-win, and keep the relationship strong for the next round.

Problem solvers are essential when:

You're working on long-term partnerships
You’ll likely deal with them again (in a week, month, or year)
There’s mutual respect in the room

They’re not pushovers. Not at all. But they believe there’s more value in building a bridge than burning one.

2. The Gunfighter

Ah yes. The devil in the title.

These folks? They want the win, and they don’t care who gets scorched in the process. Relationships, reputations, and future deals are all fair game if it means they walk away with a bigger slice of the pie.

They’re common in, and can be very effective in:

One-off transactions
Highly competitive, zero-sum industries
Toxic or desperate environments (yes, some deals are survival mode)

Roy Cohn and Gore Vidal are great examples of gunfighters. Gore Vidal may have captured the essence of the gunfighter philosophy best when he said -

“It’s not enough to win. Someone must lose.”

That is your gunfighter.

Why Knowing the Type Matters

Let’s revisit the question we asked earlier. Is this a one-shot deal or an ongoing relationship?

If this is a one-shot deal, and you’ll never see these people again, it’s possible the gun fighter style will serve you very well.

If, on the other hand, this is an ongoing relationship, and at some point in the future you’re going to find yourself doing business with these people or anyone within their sphere of influence, the problem solver style will serve you much better. With most of us, 90% of our negotiations fall within that category. They’re with customers, coworkers, procurement people, vendors, suppliers, family, etc.

Would you take a scalpel to a shootout? No. So don’t walk into a negotiation without knowing what kind of opponent (or partner) you’re dealing with.

So, how do you know when you're dealing with a gun fighter?

It looks like it would be an easy call, but a skilled gunfighter can look like a problem solver.

My grandmother said it well.
She said, “He's a wolf in sheep's clothing.”

Now that’s a dangerous negotiator.

I call them schizophrenic negotiators, and they can be hard to spot.

Don't confuse style with willingness to work with you.

Someone can be charming, affable, enjoyable to be with, but if there's no give on their part,
if they're rigid and won't give an inch themselves, you're probably dealing with a gun fighter, just a charming one.

Ongoing Relationship = Problem Solver Tools

If you’re building something for the long haul, empathy, transparency, and creativity are your best friends.

In negotiation, you’re thinking strategically, not impulsively. You’re planning moves ahead, not just reacting. In short, you’re staying calm and calculated in a heated situation.

You need:

Open-ended questions: “What’s your biggest concern here?”
Option-generation: “Here are three ways we could approach this. What stands out to you?”
Data-sharing: “Let me show you why we priced it this way.”

Mutual interests: “We both want this to succeed. How do we get there?”

One-Shot Deal = Tactical Defense Mode

But if you’re dealing with a gunfighter, especially in a one-time negotiation, you better get yourself ready. You’d better sharpen your spurs and check your armor.

You’ll need:

Clear walkaway points: When I was a kid, I remember my dad saying, "you’ve always gotta have a walk-away point. He was right. Know your red lines, and don’t cross them. We’ve all inherited bad deals, where we’ve had to work within the context of a bad negotiation, where we said, “What was this guy thinking?” He wasn’t thinking - he didn’t have a walk-away point and ended up making a bad deal, which we are now living with.
Silence: Silence is power. If you stay calm, confident, and in control, others will feel the heat before you even move. This is not easy. Learn to be comfortable with silence.
Anchoring: Start with your number, not theirs. If you've done your homework, don't be afraid to stake out the parameters of a deal.
Controlled emotion: If you don’t have one, develop a “poker face”. Show zero flinch. No nervous laughter. No over-explaining. For many people, this is gonna take some work. When I’m on assignment with clients, we video them, role-play the negotiation, and have them watch it. They’re usually surprised to see how they look from the other side of the table. People will say, I had no idea I smiled so little. Or, I look like such a grouch, or my face is an open book. You don’t need expensive cameras or a studio to do this… Your iPhone will do a great job.

Decoy concessions: Let them “win” something unimportant while you hold the line on what really matters.

The Tools of the Trade: Side-by-Side

Tool/Approach Problem Solver Gunfighter

Intent Mutual resolution Dominance/winning

Communication Style Open, empathetic Direct, strategic silence, controlling

Concessions Collaborative give-and-take Tactical, often withheld or conditional

Focus Interests Positions

Emotion Calm, collaborative Cold, sometimes aggressive

Relationship Value High Low (unless leverage tool)

Metrics for Success Mutual satisfaction Victory (you lose, they win)

So… What Do You Do When You’re Facing the Devil?

Good question. Because unfortunately, life isn’t just black and white, right and wrong, yes or no, good or bad. Life is more complex, full of nuance, gray areas and diversity and experiences, and identities. Sometimes the devil wears Prada. Other times, they’re just wearing your next paycheck.

Here are five battle-tested tactics you can use when you’re face-to-face with a hard-nose negotiator:

1. Get Control of Your Emotions

Gunfighters love the first crack in the armor. That nervous smile. The “Well, maybe we could…” as you trail off into compromise.

Don’t do it.

Silence is your ally. When they drop their outrageous demand or anchor low, don’t rush to respond. Take a beat. Let the moment sit. The first to speak often loses ground.

2. Know Your Numbers (And Theirs)

Knowledge is leverage. If you don’t know the true value of your offer and what alternatives your opponent has, you’re toast.

Research their pain points. Know your bottom line. Walk in prepared to educate them on why your offer is what it is.

Gunfighters bluff. Problem solvers reason. You need to be ready for both.

3. Use Concessions Strategically

If you must give something up, give it up slowly and with strings attached. Swap-out for something. When you do this, be sure you are aware of the difference between an ultimatum and a swap out. An ultimatum can put you in a corner, and it closes the door on creativity.

Here’s an example of an ultimatum:
“Oh, you need a lower price? Okay, we can shave 3% off if you double the order size.”

What if they can’t double the order size?

There’s always something else that would serve us just as well.
What if they could:

Waive the warranty fee
Extend the deadline/timeline on a project

Agree to open a new branch in Toronto
Give us free shipping
Guarantee early delivery
Offer better terms on payment
Expand our work-from-home rules

Ultimatums limit creativity. Here’s a rule that will serve you well in any negotiation.

Go into every negotiation with six swap-outs in your hip pocket and think them through in advance. Don’t try to come up with these when you’re at the table.

Make every concession a two-way street. Even gunfighters respect that.

4. Name the Game (Without Calling it Out)

Sometimes the best move is to name what’s happening subtly.

Say something like:

“Hey, I get the sense you’re trying to really squeeze this deal down to its bare bones. I want to make sure it’s fair for both of us, long-term or not.”

You’re not accusing them of being ruthless. But you’re showing you’re not here to get steamrolled either. It’s a gentle boundary. A respectful mirror.

5. Be Willing to Walk

We’ve said this before, but it’s so important it’s worth repeating. The strongest negotiators are those who are willing to walk away.

Yes, even if you need the deal. Especially then.

This is often referred to as your BATNA- the best alternative to a negotiated agreement

If you make it clear through posture, tone, and strategy that you can walk, even if you don’t want to, you instantly shift the power dynamic.

Gunfighters respect power. Show them yours.

What If You’re the Gunfighter?

Let’s be honest.

Sometimes you need to be the devil. And that’s not always a bad thing. There are moments, especially in short-term, high-stakes negotiations, where being assertive, direct, and unmoved can save your team millions.

When that’s the case, are you up for it? Most of us negotiate from habit. If you’re a natural problem solver, it may be very difficult for you to shift into a gunfighter mode. On the other hand, if you’re a natural gunfighter, working with other people to find a creative solution just may not be your cup of tea.

If you’re a gunfighter, know when to holster your weapon.

Overusing the gunfighter model scorches the earth. People remember. Email forwarded. LinkedIn exists.

Use the gunfighters playbook when the deal demands it, but lead like a problem solver when you can.

That's how reputations and legacies are built.

Final Thoughts: Dance with the Devil, But Don’t Sell Your Soul

Negotiation isn’t war. It’s jazz.

Sometimes it’s smooth, sometimes it’s messy. Sometimes you’re Miles Davis… sometimes you’re just trying to stay in tune.

Whatever your style, try to be flexible. Remember that not all devils wear horns and not all allies wear halos. Only by being flexible will you be equipped to read the room, shift your strategy, and walk away with a win that feels good on both sides.

So the next time you’re across the table from someone cold, calculated, and cutthroat?

Smile.

They’re not the first devil you’ve danced with. And they won’t be the last.

But you? You know the steps now.

Good negotiating to you.

Bob Gibson

“I only do three things. I teach people to negotiate more effectively.

I coach teams through important negotiations when the results matter.

I speak at associations and conventions to inform and entertain.”

If you have a need for any of those, let’s talk.

415-517-8150

bgibson@negotiatingwisdom.com

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Negotiating with the Devil – Smart Strategies for Handling Hard-Nose Negotiators