Ambassador Wendy Sherman is basically the person you call when the world is literally on fire. If you’ve spent any time looking into modern diplomacy, you know her name, but reading the not for the faint of heart book is a whole different experience than just seeing her on a C-SPAN panel. It isn’t just a dry memoir about statecraft. Honestly, it’s a masterclass in how to stay sane and effective when the person across the table from you represents a regime that wants to dismantle everything you stand for.
Most business books talk about "negotiation tactics" like they're some kind of game played in a glass-walled conference room in Manhattan. Sherman’s reality was different.
She was dealing with North Korea. Iran. The kind of high-stakes, life-and-death tension that makes a corporate merger look like a playground dispute. The book, officially titled Not for the Faint of Heart: Lessons in Courage, Power, and Persistence, pulls back the curtain on what it actually feels like to be the only woman in a room full of hardline negotiators who don't necessarily want you there. It’s gritty. It’s surprisingly personal.
The Core Philosophy of the Not for the Faint of Heart Book
The thing about Sherman is that she didn't start in the State Department. She started as a social worker. That’s a detail people often gloss over, but it’s the entire foundation of her approach.
In the not for the faint of heart book, she explains that clinical social work isn't that different from nuclear negotiations. Both require an intense, almost painful level of empathy—not the "I feel sorry for you" kind of empathy, but the "I understand exactly what you need so I can figure out how to move you" kind.
She calls it "the power of the personal."
During the Iran nuclear deal (the JCPOA) negotiations, Sherman had to manage her own team while navigating the incredibly complex emotional landscape of her Iranian counterparts. There’s a specific moment she recounts where she actually lost her temper. She yelled. She cried. In the world of high-level diplomacy, that’s usually considered a fatal error. But for Sherman, it was a calculated release of authentic pressure that actually broke a deadlock. It showed the other side that the Americans had reached their absolute limit.
Why "Authenticity" is More Than a Buzzword
We hear about authenticity all the time in leadership retreats. It’s usually fluff.
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Sherman argues that if you aren't authentic, you're predictable. And if you're predictable, you've already lost. In the not for the faint of heart book, she describes the grueling nature of the 2015 negotiations in Vienna. We're talking about weeks stuck in a hotel, eating the same food, sleeping three hours a night, and staring at the same faces. You can’t fake a persona for that long. Your true self is going to come out eventually, so you might as well lead with it.
She also touches on the concept of "courageous persistence." It sounds fancy. Really, it just means being the last person to leave the room.
Negotiating with "Evil" and Finding Middle Ground
One of the biggest criticisms Sherman faced—and continues to face—is the idea of "appeasement." People ask how she could sit across from representatives of the North Korean or Iranian governments.
She addresses this head-on.
The not for the faint of heart book makes the case that you don't negotiate with your friends. You negotiate with your enemies. That’s the whole point. If you only talk to people who agree with you, you aren't doing diplomacy; you're just being in an echo chamber.
She details the North Korea talks during the Clinton administration. It’s a fascinating, frustrating look at how close the world came to a different path. She worked alongside Madeleine Albright—another powerhouse—and the book serves as a bit of a tribute to that era of "shoe-leather diplomacy."
The Strategy of the Pivot
Sherman talks about the "pivot" a lot. Not the Silicon Valley kind where you change your app from a dog-walker locator to a crypto-wallet.
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Her pivot is about shifting your internal state.
When a meeting is going south, or someone insults you, or a deal falls apart at 3:00 AM, you have to pivot from frustration to curiosity. Why did they say that? What is the fear behind that specific demand? By shifting into an investigative mindset, she removed her own ego from the equation.
How to Apply These Lessons if You Aren't an Ambassador
You’re probably not negotiating nuclear enrichment levels tomorrow. But you might be dealing with a toxic boss, a failing partnership, or a high-stakes sales pitch.
The not for the faint of heart book offers a few tactical takeaways that work in any high-pressure environment:
- Acknowledge the Elephant: Sherman was often the only woman in the room. Instead of pretending it wasn't a factor, she used it. She knew her presence disrupted the expectations of the men across the table. She used that "otherness" to create openings that a man in her position might not have found.
- The 1% Rule: Sometimes, you can’t get a 100% agreement. You might not even get 10%. But if you can find 1% of common ground—even if it’s just agreeing on what time the next meeting starts—you have a foundation.
- Know Your "Walk-Away": You can’t negotiate effectively if you aren't willing to fail. Sherman is very clear: persistence is key, but you have to know exactly where your red line is. If you don't know your red line, the other side will eventually find it for you.
The Reality of Public Service
The book isn't all victories. It’s actually quite heavy on the toll this work takes.
The not for the faint of heart book dives into the personal sacrifices. The missed holidays. The physical exhaustion. The brutal political theater of Senate confirmation hearings. It’s a reminder that "power" isn't just about giving orders; it's about the stamina to endure the process.
Sherman’s writing is surprisingly accessible. She doesn't hide behind "state-speak" or overly academic jargon. She talks about her family. She talks about her hair. She talks about the silver bracelets she wears as a sort of armor.
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It’s these human touches that make the book rank so highly for people looking for real leadership advice rather than just another business "how-to."
Persistence in the Face of Failure
There’s a lot of talk today about "resilience." Sherman prefers "persistence."
Resilience implies you bounce back to where you were. Persistence implies you keep moving forward, even if you're limping. The not for the faint of heart book documents plenty of setbacks. The JCPOA, for instance, was later dismantled by the Trump administration.
For many, that would be a crushing defeat that invalidates years of work. Sherman takes a longer view. She argues that the work itself—the creation of the framework, the establishment of channels of communication—has intrinsic value regardless of the political winds.
It’s a perspective that is sorely needed in an era of short-term thinking.
Actionable Steps for Your Own "Negotiations"
If you’re looking to take something away from Sherman’s experience today, start with these three things:
- Audit your "Personal Power": In your next difficult conversation, stop trying to be the "professional" version of yourself. Try being the real version. If you're frustrated, state it calmly. If you're confused, ask. Authenticity breaks down defenses faster than any script.
- Map the Interests, Not the Positions: In the not for the faint of heart book, Sherman explains that what people say they want (their position) is rarely what they actually need (their interest). Before your next big meeting, write down what you think the other person is actually afraid of losing.
- Practice the "Long Game" Silence: One of Sherman’s favorite tools was silence. In a world that values quick answers and fast talking, the person who can sit comfortably in a silent room for thirty seconds longer than everyone else usually gains the upper hand.
The not for the faint of heart book isn't just a history lesson. It’s a blueprint for anyone who has to navigate a world that isn't always fair, isn't always kind, and definitely isn't for the faint of heart.
Whether you're leading a small team or just trying to navigate a difficult family dynamic, the principle remains the same: show up, be real, and don't blink first.
To dive deeper into these concepts, consider mapping out your own "negotiation ecosystem." Identify the stakeholders in your life or career who represent the "hardline" positions and apply Sherman's "empathy as a tool" strategy. Observe the results over a two-week period. You'll likely find that understanding the "why" behind an opponent's stance provides more leverage than any aggressive tactic ever could.