Trump’s Negotiation Tactics: Lessons Learned and How to Avoid Risking It All
Ever feel like you’re walking away from a deal thinking, “Wait, did I just agree to that?” Well, if there’s one person who’s made a career out of getting the upper hand in negotiations, it’s Donald Trump. Love him or hate him, you can’t deny that his ability to close deals—whether in business or politics—has had an impact.
That said, while we can certainly learn a lot from his bold tactics, some of them come with risks that can backfire if you’re not careful. Let’s break down Trump’s most famous strategies, what you can learn from them, and how to navigate your way through negotiations without going up in flames.
Lesson 1: Take a Stand and Stick to It—Like a Stubborn Goat (But Not Too Stubborn)
Trump’s approach to negotiation often starts with taking an uncompromising stance. When he developed the Grand Hyatt Hotel in New York, he boldly demanded a major tax break from the city—a request most developers wouldn’t dream of making. Trump pushed and persisted, refusing to take no for an answer. Eventually, after a long battle, he got exactly what he wanted: a tax break worth million.
What’s the lesson?
There’s power in standing your ground. When you show confidence and determination, it signals to the other party that you’re serious and won’t be easily swayed. But be careful—being too rigid can backfire. If you dig your heels in too deep, you risk alienating the other party or missing out on a deal altogether. The key is knowing when to push and when to bend. It’s like a game of poker: sometimes you bluff, but you always know when to fold.
Pro Tip:
Don’t make every point a hill to die on. Pick the few key issues you’re unwilling to compromise on but be flexible on the smaller details. That way, the other side feels like they’re winning something too, while you still secure what really matters.
Lesson 2: Patience is Key—But Don’t Fall Asleep at the Wheel
Trump knows how to play the long game, and nowhere was this clearer than in his Atlantic City casino deals. When he was building the Trump Taj Mahal, financial troubles loomed over the project. Instead of panicking and making hasty decisions, Trump held out, believing he could secure the necessary financing. He knew his casino would eventually be too big to fail. Investors were nervous, but Trump kept his cool, and eventually, the funds rolled in.
What’s the takeaway?
In negotiations, patience can be your best friend. When the other side is in a rush, they’ll make mistakes, and that’s when you step in and take control. Patience allows you to see how things develop and spot opportunities you might have missed by jumping the gun.
Pro Tip:
While patience is critical, make sure you’re not dragging things out so long that the deal loses momentum. Keep the conversation alive, but don’t force it. Timing is everything—know when to wait and when to strike.
Lesson 3: Know What Makes Them Tick—Then Press the Right Buttons
One of Trump’s greatest skills is his ability to figure out exactly what the other side wants and leverage it to his advantage. Take his deal for the golf resort in Aberdeen, Scotland. Initially, local authorities were skeptical of his plans, fearing environmental damage and local opposition. But Trump knew that what the government really wanted was jobs and economic growth in the region. So, he reframed the conversation, emphasizing the positive impact his resort would have on employment and tourism.
What’s the lesson?
Successful negotiators don’t just focus on what they want—they dig deep to uncover what the other side needs. By understanding the true motivations behind the other party’s decisions, you can structure your proposal in a way that aligns with their interests while still achieving your own goals. It’s all about making the deal irresistible.
Pro Tip:
Ask questions, listen carefully, and pay attention to non-verbal cues during negotiations. Often, what people don’t say is just as important as what they do. Once you’ve figured out their true motivations, tailor your pitch to show them how saying “yes” benefits them directly.
Lesson 4: Start High, Then Come Down—But Know When to Stop Sliding
Trump is famous for starting negotiations with sky-high demands. It’s a tactic designed to create room for negotiation later. Take the Aberdeen golf project again—he initially proposed a massive, controversial development. The plan caused an uproar, but this was part of Trump’s strategy. By proposing something extreme, he was able to offer “compromises” later that seemed more reasonable, but still allowed him to secure the core parts of his plan.
What’s the takeaway?
Always aim high in negotiations. Your initial offer should be above what you’re willing to settle for, leaving room for negotiation. This approach makes any concessions you offer feel more significant to the other party, even if you’re still getting what you wanted all along.
Pro Tip:
Don’t go so high that you lose credibility. If your initial demand is too far-fetched, the other side might not take you seriously or, worse, they might walk away altogether. The trick is to start high enough to allow negotiation but not so high that you seem unreasonable.
Minimizing Risk: Don’t Gamble Like Trump
Trump’s tactics may work for him, but they can be risky. If you always go in with a sledgehammer, you might end up breaking things that can’t be fixed. Here’s how to use Trump’s boldness while minimizing your own risk.
Balance Strength with Flexibility:
Trump is known for his “my way or the highway” approach, but in the real world, that doesn’t always fly. Being flexible doesn’t mean being weak—it shows that you’re willing to work together to find a solution that benefits both sides. It’s about finding that sweet spot between standing firm on your key issues and being open to compromise where it makes sense.Think Long-Term, Not Just Short-Term Wins:
Trump’s deals often focus on immediate victories, but successful negotiations also build long-term relationships. Instead of burning bridges with a win-at-all-costs attitude, aim for a win-win scenario. This builds trust and encourages future collaborations. Remember, it’s better to win the war than just one battle.Have a Backup Plan (or Two):
Trump’s strategy often involves taking big risks, but you should always have a contingency plan in case things don’t go your way. Whether it’s walking away, finding a middle ground, or leveraging other opportunities, don’t leave yourself with only one path to success. If the deal falls through, make sure you’re not left empty-handed.Keep Emotions in Check:
Trump is known for his fiery personality, and while passion can be persuasive, letting emotions drive your negotiations can cloud your judgment. Stay calm, collected, and clear-headed, even when the stakes are high. Cooler heads always prevail.
Wrapping It Up: Learn from Trump, But Find Your Own Groove
Trump’s negotiation strategies can teach us a lot about standing firm, reading the room, and pushing for the best deal possible. But as with all things, moderation is key. Don’t go full Trump—take the lessons that work, but leave behind the high-risk, high-drama parts that might not serve you in the long run. Negotiation is both an art and a science, and mastering it means knowing when to push, when to yield, and when to walk away.
Your Turn:
Have you ever used any of these bold negotiation tactics? Or do you have your own go-to methods that never fail? Let’s talk strategy in the comments below—I’d love to hear how you approach the deal-making game!
