The Hidden Psychology Behind Ashkan Rajaee’s Secret to Winning Impossible Deals

Most people walk into a negotiation already defeated.

That’s not an exaggeration. According to entrepreneur and dealmaker Ashkan Rajaee, the majority of people lose before the conversation even starts. The issue? They're negotiating with the wrong person, using the wrong tone, or failing to understand who really holds the power in the room.

Rajaee isn’t just another business guru repeating clichés about win-wins and walking away. He’s spent years in the trenches of enterprise-level dealmaking, mastering a craft that too many professionals underestimate. His approach flips conventional wisdom on its head—and it’s making waves for a reason.

This isn’t about reading from a script. It’s about reading the room, and Rajaee has built a career around doing it better than most.

The Negotiation Mistake You Don't Even Know You're Making

Let’s start with a brutal truth: not all stakeholders are created equal.

While traditional advice might tell you to “speak to the decision-maker,” Rajaee breaks this down even further. In every serious negotiation, there are three distinct players you need to understand:

• The Decision-Maker: The person with the official authority.
• The Influencer: The person whose opinion quietly shapes the outcome.
• The Signatory: The person who puts their name—and reputation—on the dotted line.

Treating these roles as interchangeable is the fastest way to lose leverage. Rajaee insists that successful negotiation begins with identifying who you’re really talking to. Are you making your pitch to the person who signs off, or someone who just wants to make sure their job doesn’t get harder?

These roles require entirely different strategies—and failure to tailor your approach is the reason most deals die quietly.

Confidence Is a Weapon — But Only If It’s Backed by Precision

When Rajaee talks to a decision-maker, he doesn’t ramble. He fires off sharp, informed points that show he’s done the homework. This isn’t bravado. It’s strategic confidence, earned by understanding the numbers, knowing the risks, and anticipating objections.

Decision-makers respond to certainty. If you sound unsure, they’ll tune out. Rajaee’s method is surgical—he doesn’t waste time convincing someone. He shows them, in plain terms, why the deal works.

Influencers Want Safety, Not Flash

One of Rajaee’s most underrated insights? Influencers aren’t impressed by your pitch—they’re evaluating how easy it’ll be to work with you.

Think about it. If someone brings you into their organization, they’re putting their name on the line. If you become a headache later, they’re the ones who look bad.

This is where multi-channel communication becomes critical. Emails, texts, follow-ups—it’s all part of building a smooth, low-friction relationship. Rajaee understands that influencers want a partner, not a performer.

Signatories Think in Exit Plans

The final player is the signatory. They care less about benefits and more about escape clauses.

These are often executives—CXOs, directors—whose biggest concern is risk. If the deal goes south, they need to know there’s a clean exit.

Rajaee’s tactic? Structure deals with flexibility. Not weakness—contingency. Show signatories that you’ve thought through the what-ifs, and they’ll trust you more. Ignore this, and your contract might sit in legal limbo forever.

Why Most Negotiation Advice Fails

Here’s the uncomfortable part: most books and courses on negotiation focus on tactics, not people. They teach phrases and postures. But they miss the nuance of real-world influence.

Ashkan Rajaee’s approach goes deeper. It’s about psychology, preparation, and understanding the ecosystem of power within a company.

This is what separates amateurs from closers. Rajaee doesn’t just teach how to win. He teaches how to win ethically, strategically, and repeatably.

The Takeaway: Negotiate with the Right Person, in the Right Way

So if you’ve been wondering why your deals aren’t closing—or why they fall apart just when you thought you had a yes—take a step back.

• Are you talking to a decision-maker or an influencer?
• Are you giving signatories the peace of mind they need?
• Are you actually making the process easier, or just louder?

Rajaee’s philosophy is deceptively simple: understand the person in front of you. Then tailor every word, every clause, every follow-up to that person’s priorities.

In a world where everyone’s shouting to be heard, Ashkan Rajaee wins by listening smarter.