How to Gain Negotiating Advantage with Iran

The war has exposed the limits of military superiority when it's not backed up by competent diplomacy.

Image created by ChatGPT/OpenAI.

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Let’s be honest. No one expected last weekend’s U.S.-Iran talks to succeed — and the reason had much more to do with the U.S. team’s diplomatic incompetence than Iranian intransigence. Unless the Trump administration realizes that diplomacy isn’t improv and fundamentally changes its approach, the second round of planned negotiations is again doomed to failure.

Before outlining what those changes should look like, let’s review the main mistakes the administration made in the first round — because they weren’t incidental. They revealed a deep misunderstanding of what diplomatic negotiation is, and why military superiority, if not backed up by professional diplomacy, provides only limited advantage.

Yes, diplomacy is a profession with specific skills that must be acquired and honed, as I wrote in The New York Times years ago. Common sense, intelligence and proximity to power are woefully insufficient. You can’t just wing it. Had the two-week ceasefire agreement with Iran struck last week been handled competently, there wouldn’t have been “confusion” about whether it included Israel’s war in Lebanon.

It’s ironic to discuss the administration’s misunderstanding of diplomatic negotiation, because its two chief international envoys, Steve Witkoff and Jared Kushner, have conducted multiple negotiations. Yet they have repeatedly improvised and shown no desire to learn the required skills, instead falling back on their business experience.

Why is it so difficult to understand that business dealmaking isn’t the same as diplomatic negotiation? And what does it say when a superpower’s top peacemakers aren’t willing to learn from mistakes — or even acknowledge them?

Behind the failure

The delegation’s composition — including Vice President JD Vance, another amateur in diplomacy — was the first failure of last weekend’s talks with Iran. The second was the lack of preparation. Effective negotiations begin long before delegations enter a room. They require clearly defined objectives, a hierarchy of priorities and an understanding of both the desired end state and acceptable compromises.

None of that was evident. Instead, the administration projected ambiguity about its goals — whether it sought a limited de-escalation, a broader regional arrangement or a pathway back to a nuclear framework. In this case, ambiguity wasn’t a tactic but a liability. When one side is unclear about its objectives, the other side defines the terms of engagement by default.

The third mistake was the lack of message discipline. In the days leading up to the talks, U.S. officials sent mixed and sometimes contradictory signals — publicly and privately — about what they wanted and how far they were willing to go. Negotiations aren’t only about what is said at the table. They are shaped by everything said before, during and after.

Fourth, the administration failed to establish convincing leverage before entering the talks. Leverage isn’t created at the negotiating table. It’s built in advance through coordinated political, economic, diplomatic and military measures that shape the other side’s calculations. But that doesn’t mean issuing reckless threats to obliterate “an entire civilization,” in Trump’s now-infamous words.

The Iranians have spent decades refining their negotiating approach. They are patient, methodical and disciplined. They rarely negotiate for immediate outcomes. Instead, they seek to shape the process itself — to buy time, extract concessions and test the other side’s resolve. Even if such an opponent has few cards to play, entering talks with it without a coherent strategy isn’t just risky. It’s self-defeating.

Fifth, Trump’s insistence on “alternative facts” — no, there hasn’t been regime change in Tehran — has infected the premises of U.S. decision-making. We know he lives in his own reality, but this is too serious to ignore actual facts on the ground.

Finally, there was a failure to understand the opposing side. Iranian negotiators don’t separate diplomacy from domestic politics or strategic signaling. The positions they take serve multiple audiences — internal factions, regional partners and adversaries alike. Ignoring that reality leads to misreading their intentions and flexibility, and to missed opportunities to exploit divisions or apply targeted pressure.

I often write about empathy as a diplomatic tool — the ability to understand the other side’s interests, motivations and way of thinking, so you can anticipate what it might do, and what arguments might shift its position. Empathy, of course, isn’t a word in Trump’s vocabulary.

Correcting the mistakes

If the administration wants to gain a negotiating advantage in the next round of talks with Iran, it must correct these errors — not superficially, but structurally. The recommendations below are mainly about diplomatic process, rather than policy. They reflect the best practices outlined in my book “Diplomatic Tradecraft” and the training approach at the Washington International Diplomatic Academy, which I lead.

First, the administration should bring professional diplomats in from the cold and allow them to do their job, alongside experienced nuclear and other subject-matter experts. Although the administration forced out many senior Foreign Service officers, plenty remain who are trained to serve the national interest regardless of who occupies the Oval Office. Trump’s hostility toward them must end. They can be trusted.

Second, the negotiating team needs clear and realistic instructions from the White House. It must define its objectives with precision. That means identifying not just what it wants, but what it’s willing to trade and what it won’t concede under any circumstances. Negotiators cannot improvise strategy in real time, although they can shift tactics when earlier ones no longer serve the strategy.

These decisions should emerge from internal debate within the administration, with space for alternative and dissenting views. Despite what Trump believes, he doesn’t know everything, and his instincts are often wrong. Yes, he has the final say, but he should consider all reasonable options.

Third and equally important is sequencing. The United States shouldn’t attempt to resolve every issue at once. Comprehensive agreements are appealing in theory but rarely achievable at the outset. A more effective approach is to break the negotiation into phases, each with clearly defined goals and reciprocal steps. This creates momentum, builds confidence and allows both sides to test each other’s commitments without overexposure. Everything agreed on should be written down before moving on to the next item to avoid future misunderstanding and confusion.

Fourth, the administration must adopt message discipline. Every public statement, leak and diplomatic signal should reinforce a single, coherent narrative. That narrative should make clear that the United States is prepared for serious negotiations, but not at any cost or under artificial deadlines.

Fifth, decisive leverage must be built before returning to the table. That requires a coordinated effort with allies and partners — particularly in Europe and the Middle East — to align positions and demonstrate unity. It also requires a calibrated mix of pressure and incentives. Pressure without a credible off-ramp hardens resistance. Incentives without pressure invite delay. The balance between the two is what shapes behavior.

Sixth, the administration should invest in understanding and exploiting the dynamics within Iran’s leadership. Negotiations are rarely conducted by monolithic actors. They involve competing interests, institutional rivalries and shifting political constraints. Identifying where flexibility exists — and where it doesn’t — is essential to crafting proposals that can be accepted and implemented.

This doesn’t mean accommodating Tehran’s preferences. It means recognizing that successful diplomacy requires more than pressure. It requires an ability to frame outcomes in ways that the other side can justify domestically without appearing to capitulate.

Finally, the administration must be patient. The desire for quick results is one of the greatest vulnerabilities in negotiation. It signals urgency and reduces leverage. I don’t mean delaying for its own sake, but ensuring that each step serves a defined objective.

None of these recommendations guarantee success. They are just the minimum requirements of diplomatic negotiations. But ignoring them virtually ensures failure.

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Nicholas Kralev is the founder and executive director of the Washington International Diplomatic Academy, and a former Financial Times and Washington Times correspondent. His books include “Diplomatic Tradecraft,” “America’s Other Army” and “Diplomats in the Trenches.”