Saturday, August 2, 2025

How To Negotiate With Someone Like Trump – And Win

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Trump’s hard-bargaining tactics are already used in the business world by those with a clear power advantage. 
Image: ShutterstockTrump’s hard-bargaining tactics are already used in the business world by those with a clear power advantage.
Image: Shutterstock

United States President Donald Trump’s negotiation approach has upended international affairs, marking a radical change to previous decades of global diplomacy and leaving world leaders struggling to respond effectively. Many have failed to understand the strategy and moves Trump uses and have responded in suboptimal ways.

Trump’s hard-bargaining tactics are already used in the business world by those with a clear power advantage. If his presidency proves successful, his negotiation strategy may be emulated by business negotiators worldwide, and many will find themselves facing a Trump-like negotiator across the table. Unfortunately, most descriptions of Trump’s negotiation approach often fail to grasp critical nuances, leading negotiators to follow unproductive approaches.

So, how should you negotiate effectively with someone like Trump? Many world leaders seem to believe that they must either obtain more power than him (which is theoretically correct, but close to impossible for most to achieve in the short term), ignore the power difference altogether and attempt to negotiate as equals, or just give in to avoid the pain or risk of confronting his hard tactics and suffering his retaliations. These are three basic mistakes that will send any negotiator toward failure in this context.

To be clear, we are not supporting Trump’s negotiation approach, nor are we criticising it. Ultimately, we aim to help readers understand the methods he uses and negotiate the best possible outcome with those using similar tactics.

Trump, and those who use similar negotiation tactics, often follow what we define as the hard-bargaining approach. This typically involves applying one’s power advantage to extract value from the counterparty without much consideration for the relationship or their perception of fairness.

Hard bargainers also adhere to a business-like sense of fairness. While many argue that Trump doesn’t care about procedural or interactional fairness (rules, rights, respect and relationships) or some views on distributive fairness (outcomes), such as needs-based fairness, he upholds the idea that those who contribute more should also receive more. These kinds of hard bargainers believe that if someone provides significant value, they deserve significant compensation. If others fail to reciprocate, there is no obligation to continue one’s end of the bargain.

Trump-like characters tend to frame situations as unfair deals. For instance, Trump believes the American people have been on the losing end of an unfair global exchange due to US negotiation complacency, and sees this as a crisis demanding urgent, drastic action. This logic or rationalisation is consistent with what most companies would adopt anywhere in the world if they saw they were losing money or market power.

Also read: India-US Trade Deal: Farm Imports Blocked

How do I negotiate with hard bargainers like Trump?

Trump’s general demeanour may lead many to hate, fear and underestimate him. Why is this problematic? Many of Trump’s counterparties have been negotiating under the influence of these emotions or perceptions, aiming to stand up to him rather than pursuing the best possible outcome. Our core advice for anyone dealing with someone like Trump is that fighting fire with fire is a losing strategy when negotiating from a less powerful position. Your fire is likely to burn out sooner, leaving you with nothing but ashes.

What not to do

1. Don’t disregard the power difference

A common mistake we see when people try to negotiate with Trump, or others in a dominant position, is ignoring, dismissing or showing indifference to their power advantage. The ensuing negotiation dynamic tends to be the following: Trump wants a high-value deal that reflects his superior power position. The counterparty dismisses Trump’s power advantage; be it due to failing to see or discounting the role of power in their exchange; insisting on resolving their differences through fairness alone; or making or threatening retaliatory moves.

To overcome this resistance, Trump or other hard bargainers will likely want to make their power advantage clearer. This triggers worse interactions, after which it becomes much harder for both sides to pivot toward collaboration and value creation.

2. Don’t publicly make them look bad

People like Trump care about their image. Eroding their image is akin to attempting to reduce their power, which will likely invite a strong and immediate response. Yet, there are many negotiators whose approach has been based on trying to make Trump look bad. It’s critical to understand that power is not bravado. Trump will attempt to negotiate collaboratively with those like Russian president Vladimir Putin who, given the latter’s position as the head of a nuclear superpower, he doesn’t have a large power advantage over. However, he is unlikely to do the same with someone who acts like Putin but lacks the power to back it up.

Having a power advantage usually means that Trump can sustain the consequences of a conflict better or longer than the other side can. It’s naïve to expect that he will not try to restore his image by gaining one up on his counterparty, or that he will disregard his image and prioritise the deal’s economics. As such, those who make Trump – or anyone borrowing from his playbook – look bad publicly are likely to pay the price later unless they are powerful enough to avoid it.

3. Don’t let them influence your measure of success

When negotiating, one should focus on getting the best deal, as measured by one’s own absolute measure of success. Negotiators should not strive to arrive at an outcome that is necessarily equal. Indeed, negotiating towards a 50/50 split with someone like Trump often makes one pursue a highly ambitious and unlikely goal, which forces negotiators to take more risks than advisable, given their lower power position.

Alternatively, some negotiators may do the reverse. Instead of reaching for more for themselves, they attempt to worsen the deal for the hard bargainer relative to theirs. Both approaches raise the chances of them becoming more aggressive and less collaborative, leading to a smaller pie at the end of the negotiation. Also, be very careful that their initial proposal (which is an extreme anchor) does not influence your measure of success. Let that proposal inform the interests you will want to satisfy in the negotiation, and move on.

4. Don’t focus your preparation on increasing your power

All else being equal, having more power in a negotiation is much better than not having it, and some world leaders should have focused on increasing their power in years past. But all else is not equal when preparing to negotiate with a much stronger hard bargainer like Trump.

First, your preparations risk signalling that you are preparing for a battle, and may invite a pre-emptive strike. Given that the other party is more powerful than you, you’re very likely to lose that fight. Second, by investing your preparation time into thinking of how to overpower the other side, you risk ignoring or underestimating how they might retaliate, fall prey to groupthink or overestimate your real power.

Third, once you go down the road of coercive power on both sides, it tends to lead to escalation which, in the case of Trump’s power superiority over most negotiation counterparties, he’s likely to win. Finally, by focusing on power-based preparation, you risk wasting your limited time preparing for the wrong game. Just think: What if world leaders had taken a more agnostic perspective on the US election and prepared to find solutions that would work for whoever won?

What to do

1. Signal a clear and early intention to negotiate a good deal

Indicate that you are aware of the person’s power and are happy to negotiate – within your capabilities – with the intention of giving them a good deal. That way, they no longer need to keep applying their power to convince you. You are already helping them translate their power into value, thus signalling that you aren’t a threat to their goals. This advice may make many negotiators feel extremely uncomfortable, as our intuition and emotional nervous system push us towards a fight-or-flight response in the face of such power displays.

Once this initial signalling groundwork is done, listen and ask about their interests, then share yours as well. If they put forth their legitimacy arguments (e.g. a transactional view of fairness), acknowledge (but don’t agree) with them and signal your collaborative intention. There is no need to accept any proposals at this stage. Then, show that you can focus on crafting the best possible deal so they feel no further need to talk about power and are ready to discuss value instead.

2. Create value for both parties

Once you’ve shown an intention to work out a good deal, engage them in optimising the deal for both sides. In the case of a businessman like Trump, he likely wants to forge deals that generate value for him and can make him look good in the media. Here, Trump can actually be a preferred counterparty to more traditional government officials, who are often risk-averse and not reward-seeking.

Rather than following zero-sum thinking and only focusing on defending what a hard bargainer is trying to take from you, reframe the negotiation as a positive-sum opportunity and focus on improving the deal for both sides. Even if the deal turns out to be, for instance, two times better for them than it is for you, it’s worth it if that means getting a better deal for yourself.

3. Negotiate through the lenses of power and value

Instead of refusing what they are asking for, think about their value potential and power advantage. If giving them what they want would be very costly, ask them willingly and genuinely, as former FBI hostage negotiator Chris Voss suggests: “How do you expect me to do that?” and explain the difficulties that must be overcome for the request to become possible.

You are not stubbornly refusing to give them what they want; hence, you are not a problem they need to bend. You are simply sharing the difficulties with them so they can use their power and resources to find solutions that work for both sides. Like any negotiator, hard bargainers can take pride in devising creative solutions or solving problems to reach a deal, such as suggesting ways to create value for you in other areas, so you can satisfy their interests.

Negotiating with someone like Trump should be based on accepting the power difference and then working with them to make the deal valuable for all. Negotiators aiming for success will be better off not getting into public arguments or escalations of power, which they are very likely to lose; having a crisp understanding of and avoiding confusing the roles of power, value and fairness in negotiations; and preparing diligently to maximise value for both sides. By pursuing the right moves and avoiding high-risk ones, we believe that anyone can negotiate better and craft superior deals – even with the toughest of hard bargainers.


[This article is republished courtesy of INSEAD Knowledge, the portal to the latest business insights and views of The Business School of the World. Copyright INSEAD 2025]

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