by Andres Lares, Managing Partner at Shapiro Negotiations Institute and co-author of “Persuade: The 4-Step Process to Influence People and Decisions”
Whether you love him or loathe him, there’s no denying that President Donald Trump has a newsworthy negotiation style. Before the presidency, Trump built a real estate empire on bold asks, strategic media plays, and relentless deal-making. Strip away the politics, and what remains are raw, high-stakes negotiation tactics entrepreneurs can learn from- what to do and what to avoid, especially in today’s competitive business landscape.
Here are five Trump-style power moves to level up your negotiation game.
1. Extreme Initial Positions → Don’t Be Afraid to Ask Big.
Trump rarely enters a negotiation with a modest offer — and that’s the point. Starting with a bold, even outrageous, ask creates psychological space to move while still landing in a strong position. Entrepreneurs often make the mistake of being too reasonable too early, which leaves no room to maneuver.
If you’re taking a page from his playbook, go big. Ask for more funding than you “need,” price your premium offer accordingly, or negotiate equity from a position of clear value. You can always concede but you can’t negotiate up from a weak starting point. Starting big will shift the tone of the conversation from “Is this worth it?” to “How close can we get?”
This begs the question: how high should the initial ask be? As high as you can justify with precedents and comparables. Trump may not always follow this guidance, but we certainly recommend you do.
2. Threat of Consequences → Leverage What’s at Stake.
Trump often positions himself as the prize, not just another option. He frames the consequences of walking away in terms that make it feel like a loss to the other party. Entrepreneurs can do the same without resorting to pressure tactics.
Instead of begging for interest during your next negotiation, paint a picture of what the other party stands to miss: early access to your tech, first-mover advantage in a growing niche, or protection from a competitor making a better offer. Make the upside of working with you crystal clear and the downside of missing out.
Psychologically, fear is typically a bigger driver than achievement. In other words, the thought of losing $10 is more powerful than the thought of winning $10, even if the changes are the same. Keep this in mind the next time you frame an offer.
3. Public Posturing → Own the Narrative and Build Perception.
Trump knows how to use the media to create momentum. Whether in a press release, a public statement, or a tweet, he understands that perception is power. The more he is seen as a winner, the more leverage he has — even behind closed doors. He accomplishes this by constantly being “out there” in public, often intentionally making attention-grabbing comments.
Entrepreneurs can harness this same dynamic through strategic storytelling. Share client wins, publish testimonials, showcase press coverage, and keep your audience informed. The perception of growth creates confidence in your value, even if you’re still building behind the scenes. Your story shapes how investors, partners, and clients approach negotiations with you.
4. Unpredictability → Keep Some Cards Close.
Trump is rarely predictable, and that unpredictability often puts others on edge. While unpredictability can be bad for stock markets and create global volatility, being slightly opaque about the next move can be a form of negotiation power. Predictability can be exploited.
What does this mean for you? Avoid showing all your cards too early. Be clear about your value but vague about your limits. This doesn’t mean being deceptive; it means being strategic. Leave space for curiosity and calculated surprises. A little mystery can prevent the other party from boxing you in, and it forces them to take your position seriously.
5. Bilateral vs. Multilateral → Prioritize One-on-One Conversations.
Trump often pushed for direct, one-on-one deals where he could influence and steer decisions in real time. In contrast, negotiations with multiple stakeholders slow things down, complicate messaging, and dilute your impact.
When it matters most, skip the group calls and get in the room with the decision-maker. In a one-on-one setting, you can read the room, build trust, pivot in real time, and tailor your pitch to the person in front of you. Consensus may come later, but influence happens face-to-face.
Conclusion
Trump’s style isn’t for everyone — and it doesn’t have to be. But if you can extract the core principles behind his negotiation tactics, you’ll uncover fundamental strategies that could work. Bold positioning, strategic leverage, public perception, controlled ambiguity, and direct communication are timeless tools that separate amateurs from pros.
The key? Know when to apply each move with your voice and ethics. You don’t have to mimic Trump, but his methodology should make you think about aspects you may want to leverage and others you will want to avoid.
[Image credit: Depositphotos.com]
Andres Lares is the Managing Partner at Shapiro Negotiations