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Dare to Deal – Part 3: Mind Games That Win You The Deal

We’ve talked about deal structure, strategic unfairness… but the most powerful weapon in negotiation is often what’s going on in the other person’s head. Here’s how to use a little psychology to your advantage (without being a total sleazebag).

The Power of Silence (And How to Weaponize It)

Most people HATE awkward silences. After you make an offer, shut up. Let them squirm. Often, they’ll start justifying their position to fill the void, revealing weaknesses you can exploit.

  • The Flinch Test: Throw out a slightly outrageous number. Don’t say another word, just watch their reaction closely. A subtle flinch tells you they were expecting worse.
  • The Non-Response Response: Did they ignore your email asking for a follow-up? That’s a negotiation tactic in itself, designed to make you anxious and more likely to cave. Don’t bite.

Framing: The Language That Changes Everything

The way you present something matters more than you think. For example:

  • Anchoring: Start with an initial number that sets the ballpark, even if it’s high (or low). This biases the rest of the negotiation in your direction.
  • Loss Aversion: Instead of “What do I get?”, emphasize “What do THEY lose if they say no?”. Fear is a stronger motivator than gain for most people.
  • Scarcity Mindset: Subtly convey that you have other options, that this deal is time-sensitive, etc. Creates the urgency you need them to close.

Case Study: The “Too Busy to Negotiate” Ploy

A potential investor was stringing me along – meetings kept getting canceled, vague promises of “circling back soon”. I knew he was interested, but also sensed he was playing the power card. So, I flipped it:

  • The Busy Founder Act: I became conspicuously unavailable for weeks. Short emails with, “My schedule is insane, can we squeeze this in?”.
  • The “Accidental” Leak: Hinted at major interest from another VC in a way that seemed like it had slipped out. Didn’t even have to be true!
  • The Expiration Date: I put a time limit on my final offer, and made it clear this wasn’t a bluff. Suddenly, he was very easy to reach.

Negotiation isn’t just about numbers. It’s about controlling the narrative, and understanding what REALLY motivates the person across the table.

Trai s.

The Ethical Line

Look, I’m not saying you should lie or manipulate people. But being naive in negotiation will get you fleeced. Think of these tactics like martial arts – knowing how to defend yourself, so you can create deals where everyone wins in the long run.

Let me know if there’s a deal-making mistake you see founders make repeatedly that you want to address in a future “Dare to Deal” post!

Trai Sasatavadhana

Hi! I am a venture builder/corporate venture capitalist. I find and fuel the startups that will change the world.

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