For most people, negotiations begin with building trust incrementally—almost like building a fire. You start with kindling, then smaller branches, gradually building toward the larger logs.
(This is a preview of chapter 2 in “Trump’s Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox” by Jeffrey Sonnenfeld and Steven Tian. The book is published by Worth Books and will be released on March 31, 2026. Pre-order your copy now: https://worth.com/trumpten/)
Donald Trump doesn’t do any of that.
He starts by taking the biggest log he can find and whacking you in the face with it as his favorite opening move.
That is Trump’s way of creating maximal leverage for himself—manners and convention be damned. By inflicting maximal pain right away, anything that comes afterward will seem mild by comparison, or so the thinking goes. He hopes that his bloodied, disoriented opponents emerge from the initial onslaught all but desperate to find a solution.
It is a brute-force, blunt-trauma approach to negotiation—almost akin to ripping someone’s arm off in the belief that they will emerge grateful to have escaped with their lives having lost only an arm.
Trump’s almost predatory approach to negotiations—bite first, talk later—is fundamentally a reflection of his zero-sum worldview. Somebody must always lose for him to win, because in Trump’s world, win-wins rarely exist. If the other guy is getting something good, that’s a dollar left on the table that you should have seized. There is no such thing as trust-building, reciprocal gratitude, or long-term relationship nurturing. Everything is transactional and in-the-moment: What can I get from you right now, and how far can I push?
This is the diametric opposite of how most people are taught to negotiate. Modern negotiation theory—popularized by the Harvard model and the bestselling Getting to Yes—preaches de-escalation, trust-building, emotional regulation, and the separation of people from problems. Trump neither knows nor cares about any of this, and even if informed of it, would surely dismiss it as naïve and impractical.
Trump’s approach is escalation first, questions later. When necessary, he becomes a one-man incendiary force willing to scorch the earth before negotiations even begin. There are no sacred cows. Trump relishes challenges to precedent and orthodoxy, with flagrant disregard for common values, norms, or conventionally acceptable behavior.
There are times when this aggressive playbook allows Trump to get away with asking for things he never would have gotten otherwise. But it also can fail him in predictable ways. Most notably of all, Trump sometimes overplays his hand. By coming out swinging too hard, too early, he sometimes poisons the well beyond repair. When that happens, his response is rarely introspection. Instead, he escalates again—punching harder, staying on offense, refusing to retreat.
Escalation, however, comes at a cost—and sometimes crosses red lines that even Trump cannot stomach crossing. For example, after stocks sold off nearly 20% following his Liberation Day across-the-board tariff announcement, Trump quickly pulled back, abruptly announcing a 90 day pause in the implementation of those tariffs, with the market constraining Trump’s ambitions. Trump’s repeated tendency to bluff, threaten, and then retreat has led foreign leaders, markets, and adversaries to discount his ultimatums. When others learn that waiting him out may be the best strategy, his leverage diminishes. Wall Street analysts even coined the acronym “TACO”—Trump Always Chickens Out—a label that infuriates Trump precisely because it exposes the vulnerability beneath the bluster.
Similarly, Trump’s negotiating playbook can fail because leverage is an exhaustible supply. For example, after Trump repeatedly bludgeoned longtime foreign allies such as Canada, Canadian Prime Minister Mark Carney shocked the world when he announced at Davos his commitment to broadening out Canada’s alliances, moving past its historic alliance with the US towards a grouping of middle powers forced to stand up for themselves. In other words, the more Trump wields his disproportionate leverage to extract concessions now, the less leverage exists in the future for him to extract similar concessions. In that sense, the cost to his negotiating style is very real.
All that is the real art of Trump’s deal. It is not about trust. It is about leverage, fear, momentum, and exhaustion.
This is not how most people negotiate. But it is how Donald Trump does. And understanding that difference is the beginning of understanding Trump himself.
