One of the worst mistakes you can make during a contract negotiation is preparing for a debate when you should be gearing up for a chess match. 

In a chess match, the player who can strategize furthest into the future wins. Grandmasters excel at this predictive thinking — they map potential moves, counters, and consequences up to eight moves in advance. Their prescience allows them to make plays and sacrifices that preemptively cut off their opponent’s path to victory. 

As International Chess Grandmaster Maurice Ashley once said, “When you’re dead, I knew 10 moves ago because I knew where we were going.”

The same idea holds true in contract negotiation. If you know the metaphorical board and your opponent’s probable plays, you can execute a strategy that makes the outcome you want the only possible result. To borrow a quote from negotiation expert Chris Voss, “Persuasion is not about how bright or smooth or forceful you are. It’s about the other party convincing themselves that the solution you want is their own idea.”

Let’s apply this line of thinking to a hypothetical scenario. After weeks of debate, my opponent and I know what the other wants. While we’re relatively close on terms, we disagree on a few crucial points. Obviously, I want the deal to favor me and the other guy wants it to favor him

So, what do I do? I write a contract with a 3:1 positioning. I add in three points I know he’ll object to and order them on a scale of increasing intensity. The first point is mildly bothersome, the second objectionable, and the third a major concern. But the fourth point, the one I include at the end, is the most crucial; it refers to something I want and my opponent would normally never give me.

Negotiation day comes; I hand the contract over to my counterpart for review. It isn’t long before he flags the first trap. I express surprise at his objection but ultimately concede once he explains his perspective — we’re friendly, after all. 

Then we get to the second paragraph. 

“David, I think we have a problem here,” he says. 

I let the silence drag out for a moment. The unspoken message — two problems in two paragraphs, really? — is clear. 

“Okay,” I say, finally. “What’s the issue?” 

After he explains, I take another pause. Then, using a slow and measured tone, I say, “I see your point but I don’t necessarily agree with it all.” 

This response forces him to plead his case. It takes a few minutes before I capitulate. 

Relieved, my counterpart turns to the third paragraph — and immediately begins sweating when he sees the next point, which is worse than the last two combined. 

“David,” he tries, “I think I have a problem here.”

“Hey, are you going to have a problem with every paragraph?” I demand. “Because this is three out of three. What’s your issue with this one?” 

After he explains, I sit back. “Yeah, I don’t see that as a problem for me, sorry,” I retort. 

The following conversation is even more contentious than the last. I purposefully drag the debate out, forcing my opponent to argue twice as hard, all the while knowing that I’m going to let the point go — that I had in fact written it as a strategic sacrifice. 

By the time we finish discussions on paragraph three, tensions are high. My counterpart knows the contract is on thin ice; he can’t make any more requests without jeopardizing the deal. 

It’s at this moment that he sees the point in paragraph four — the item I want, the concession he would normally never agree to hand over. Suddenly, he realizes he only has two choices: he can object, which he knows will cost him the deal, or stay silent and let me have my victory. 

Nine times out of ten, the person on the other side of the table will choose the latter. Here’s why: by the time we get to the fourth paragraph, my opponent knows he is responsible for putting the contract at risk. If his fourth complaint ends our conversation, he will need to explain to his higher-ups why the deal fell apart. Moreover, from his perspective, I’ve been remarkably reasonable. I’ve acceded to not one, not two, but three of his requests. He feels responsible for the current tension — and his guilt works in my favor. 

You see, guilt plays what psychologists call a “prosocial” role in human interactions. As writers for one study on the matter explained, guilt “encourages taking responsibility, motivates amendatory behaviors such as apology or confession, leads to higher-quality solutions to crises [and] is also associated with positive empathy and the ability to acknowledge and understand others’ points of view.” 

In other words, people are more likely to work cooperatively and make compromises when they feel at fault. By writing a 3:1 contract that compels my opponent to make multiple objections, I’ve effectively maneuvered him into feeling responsible for the tense situation. Most people will be willing to overlook the fourth point for the sake of keeping the deal on-track. By the time we sign, I’ve gotten what I wanted out of the deal without sacrificing anything I wasn’t already prepared to give up. 

Of course, this strategy comes with some risk. If the person on the other side of the table decides to object to the fourth point — which is my dealbreaker — I walk. There’s no further conversation, no callbacks, no negotiation. I leave, and the other party doesn’t chase me. That’s the risk of the takeaway; while your opponent will probably fold, you need to be prepared to let the deal go if they refuse to bend. It’s a calculated risk, so you must do your research to make sure your odds are good before attempting it. 

Contract negotiation is an exercise in strategy. If you come to the table, approach with a checkmate play in mind.