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Say It Well

Find Your Voice, Speak Your Mind, Inspire Any Audience

4.2 (247 ratings)
25 minutes read | Text | 9 key ideas
Public speaking is an art, and few have mastered it like Barack Obama. In "Say It Well," former White House speechwriter Terry Szuplat unravels the secrets behind Obama's magnetic oratory skills, transforming them into accessible lessons for anyone looking to conquer the stage. Szuplat, who once trembled at the thought of public speaking, now invites you to join him on a journey from fear to finesse. Packed with Obama's insider tips and personal anecdotes, this book is your toolkit for captivating any audience—be it a crowded boardroom or an intimate gathering. Discover how to transform nerves into narrative power, craft speeches that resonate with authenticity, and inspire action with every word. Whether you're delivering a heartfelt toast or a passionate plea, "Say It Well" empowers you to not just speak, but to speak with purpose and confidence.

Categories

Business, Nonfiction, Self Help, Communication, Writing, Leadership, Politics, Audiobook

Content Type

Book

Binding

Hardcover

Year

2024

Publisher

Harper Business

Language

English

ASIN

0063337711

ISBN

0063337711

ISBN13

9780063337718

File Download

PDF | EPUB

Say It Well Plot Summary

Introduction

I was shaking. My heart raced as I shifted anxiously in my seat, desperately thinking of ways to escape. The voice announced, "And now, give it up for Terry!" Every eye in the room turned to me. As I began speaking, my voice trembled noticeably. The awareness that everyone could hear my nervousness only made it worse. My hands shook as I held my speech pages, creating a visible display of my anxiety. For a moment, I felt like I was floating above myself, watching this disaster unfold as the Voice of Doubt echoed in my head: "They can see you're nervous. You're going to embarrass yourself. Please, just let this be over." The journey from trembling novice to confident communicator is one we all face in different ways. Whether addressing a boardroom, teaching a class, or simply expressing our thoughts in a team meeting, finding our authentic voice remains one of life's most challenging yet rewarding quests. Through intimate stories from the highest corridors of power alongside practical wisdom from everyday communicators, we discover that effective speaking isn't about perfection or performance—it's about connection and authenticity. The path to becoming a powerful communicator begins not with mastering techniques, but with knowing ourselves and believing our voice matters.

Chapter 1: The Trembling Speechwriter: My Journey from Fear to Authority

I was shaking. My heart raced as I shifted anxiously in my seat, desperately thinking of ways to escape. The voice announced, "And now, give it up for Terry!" Every eye in the room turned to me. As I began speaking, my voice trembled noticeably. The awareness that everyone could hear my nervousness only made it worse. My hands shook as I held my speech pages, creating a visible display of my anxiety. For a moment, I felt like I was floating above myself, watching this disaster unfold as the Voice of Doubt echoed in my head: "They can see you're nervous. You're going to embarrass yourself. Please, just let this be over." The irony wasn't lost on me. Here I was, a professional speechwriter for President Barack Obama, one of history's most gifted orators, yet I couldn't deliver a simple skit at a karaoke bar in Japan without falling apart. Despite crafting words for others to speak confidently on the world stage, I had spent most of my career hiding behind the scenes, writing speeches I was too afraid to give myself. This disconnect between helping others find their voice while losing my own became the catalyst for my journey – one that would eventually lead me from paralyzing fear to discovering the power of authentic communication. My transformation didn't happen overnight. It began with small steps – volunteering for low-stakes speaking opportunities, practicing in front of trusted friends, and gradually building confidence through repeated exposure. I learned that the path to overcoming speaking anxiety isn't about eliminating fear but developing a relationship with it. Each time I pushed through my comfort zone, the voice of doubt grew a little quieter. What surprised me most was discovering that authenticity matters more than perfection. Audiences don't connect with flawless delivery; they connect with genuine humanity. When I finally stopped trying to be the perfect speaker and instead focused on communicating authentically, something magical happened – people actually listened. They responded not to polished phrases but to the sincere conviction behind my words. The journey from trembling speechwriter to confident communicator taught me that finding your voice isn't about becoming someone else – it's about becoming more fully yourself. When we embrace our unique perspective, acknowledge our vulnerabilities, and speak from a place of genuine conviction, we discover an authority that no technique can manufacture. True confidence emerges not from the absence of fear but from the presence of purpose.

Chapter 2: Sacred Stories: How Obama Found His Authentic Voice

Barack Obama wasn't always the confident speaker we came to know. In 1981, as a nineteen-year-old sophomore at Occidental College, he participated in a rally against South Africa's apartheid policy. He managed only a few sentences before two students, pretending to be South African security forces, dragged him away as part of the demonstration. "That's the last time you will ever hear another speech out of me," he told a friend afterward. "I've got no business speaking for Black folks." Years later, Obama explained to me that his struggles weren't just about his mixed racial identity but stemmed from deeper doubts about his place in the world. "I think the starting point for effective speaking, for me at least, is do they have a sense of who they are and what they believe?" he reflected. "At the rally on campus that day, I was a callow youth trying to sort out who I was and what I believed. I was nineteen years old, thinking, 'Do I deserve to be in the spotlight? Do I have something specific to say about this topic when I'm still trying to sort out who I am and what I represent?'" Obama's journey continued through various formative experiences. He learned from Chicago pastors whose powerful sermons taught him rhythm and storytelling. He honed his skills in the classroom as a law professor at the University of Chicago. Through early political campaigns, including his failed run for Congress in 2000, he gradually found his authentic voice. "When I first started running for Congress," he admitted, "I had a tendency in some settings of not telling stories, but rather listing off talking points, factoids, and policy. I was too abstract, too wonkish, and, as a consequence, too long-winded." By the time he delivered his electrifying keynote at the 2004 Democratic National Convention, Obama had integrated all these lessons. He began by sharing his personal story: "My father was a foreign student, born and raised in a small village in Kenya... While studying in America, my father met my mother. She was born in a town on the other side of the world, in Kansas." He continued, "I stand here today, grateful for the diversity of my heritage... knowing that my story is part of the larger American story." The speech wasn't just about policy positions – it was rooted in his journey of self-discovery and understanding of his unique place in American society. Obama's evolution reveals a profound truth about authentic communication: our most powerful voice emerges when we reconcile who we are with what we believe. His early struggles weren't failures but necessary steps in discovering his authentic voice. Each experience – from the awkward college rally to the Chicago pulpits to the classroom – contributed to his development as a communicator. The journey to finding our voice isn't about perfecting a technique but about embracing our story and speaking from that place of hard-won self-knowledge.

Chapter 3: The 50-25-25 Rule: Structuring Messages for Maximum Impact

One Saturday afternoon, I was summoned back to the White House because President Obama was scheduled to deliver a speech the next day on U.S. relations with Israel. I'd been working on the draft for a week and thought it was in good shape. The mood in the Oval Office suggested otherwise. Obama turned to me, holding my draft, and said, "It's not your fault, Terry, but this is not what I want to say." I was confused and felt like I'd let him down. Where had I gone wrong? The answer lay in a fundamental mistake that many speakers make – rushing to write before thinking through what they really want to say. That's why I developed what I call the 50-25-25 Rule: spend roughly 50 percent of your time thinking, researching, and organizing your thoughts; 25 percent of your time writing; and the final 25 percent editing and practicing. This approach works regardless of your timeframe. If you have a month to prepare, spend two weeks thinking and researching, one week writing, and one week editing and practicing. If you have just a week, allocate three days to thinking and research, two days to writing, and two days to editing and practice. Even if you've just been asked to give a toast tonight, spend an hour thinking, thirty minutes writing, and thirty minutes editing and practicing. During the first 50 percent of your time, I recommend a three-step process. First, scope it out – develop what I call 100% Situational Awareness by asking ten key questions about your audience, venue, and purpose. Second, think it out – determine your core message in ten words or less. Third, figure it out – research thoroughly to find the "gold nuggets" that will make your speech shine. After this preparation, you're finally ready to write. And here's another secret: every good speech, like a great play, has three acts – a beginning, a middle, and an end. When I realized this while working on a major address for Obama to deliver to the Indian Parliament, the task suddenly felt less overwhelming. I knew where I was going because, even though the speech was more than four thousand words, it all came down to three simple parts. The 50-25-25 Rule transforms how we approach communication by prioritizing thought over words. Most speaking failures stem not from poor delivery but from inadequate preparation. When we invest the majority of our time in thinking deeply about our message, understanding our audience, and organizing our ideas, the actual writing flows naturally. The structure becomes the invisible architecture that supports our message, allowing our words to land with maximum impact. By embracing this disciplined approach, we move from merely speaking to truly connecting.

Chapter 4: Speaking to Hearts: Why Emotion Trumps Data

In 2019, teenage climate activist Greta Thunberg addressed world leaders at a global climate conference in Madrid. She began with technical details: "In chapter two, on page 108 in the SR 1.5 IPCC report that came out last year, it says that if we are to have a 67 percent chance of limiting the global temperature rise to below 1.5 degrees Celsius, we had, on January 1st, 2018, 420 gigatons of CO2 left to emit in that budget." Later, Thunberg herself acknowledged the problem with this approach: "I basically only spoke about facts and numbers. And then people watched it, and it felt like no one understood a word I said." She had made one of the most common mistakes in public speaking – trying to persuade an audience with a blizzard of statistics rather than speaking to their hearts. Months earlier, Thunberg had given a very different speech at the United Nations in New York. With fiery indignation, she declared: "You have stolen my dreams and my childhood with your empty words. And yet I'm one of the lucky ones. People are suffering. People are dying. Entire ecosystems are collapsing." With each sentence, she jabbed her hand for emphasis, her voice breaking, tears welling in her eyes. This emotionally charged speech broke through and was seen around the world because Thunberg did what great speakers do – she spoke from her heart, with passion and conviction. Research confirms why speaking from the heart is so powerful. Jonah Berger and Katherine Milkman examined thousands of news articles and found that readers were more likely to share stories that triggered strong emotions. Another study of over 560,000 tweets about issues like gun safety and climate change found that tweets with moral and emotional words were 20 percent more likely to be shared than those with neutral language. This is why I urge speakers to use emotional words. Instead of saying you're "happy," say you're "proud," "optimistic," or "joyful." Rather than saying you're "angry," express that you're "frustrated," "furious," or "indignant." When you give a speech, don't just use words – use emotional words that truly convey what's in your heart and create a deeper connection with your audience. The science of persuasion reveals a fundamental truth about human nature: we are emotional beings first and rational beings second. Data informs, but emotion moves. When we speak only to the mind with facts and figures, we miss the opportunity to connect with the heart – where decisions are truly made. The most powerful communicators understand this balance, using data to support their case while wrapping those facts in emotional language that resonates at a deeper level. Our greatest influence comes not from overwhelming others with information but from touching them with authentic emotion.

Chapter 5: The Human Touch: Connecting Through Clear Language

I once visited a White House official to discuss an upcoming presidential speech. His explanation went something like this: "The old economic models haven't worked. The U.S. government needs to put more skin in the game." When I asked for details, he continued: "We're proposing a new model—public-private partnerships that leverage innovation." Seeing my confusion, he added: "There's no one silver bullet. This is about harnessing multisector collaboration." As my eyes glazed over, he concluded: "It's a real paradigm shift with potential to unleash transformational change." I left more confused than when I arrived. Why do so many people talk like this? Call it jargon, buzzwords, bureaucratese, or gobbledygook – it's not English. Yet this rhetorical nonsense infects countless presentations every day. Business executives refer to "human capital" and urge teams to "align around core competencies." Nonprofit leaders push for "blue-sky thinking" to "incentivize best practices." Financial experts speak of "calibrating risk premiums" instead of simply explaining what they mean. This affliction has a name: the Curse of Knowledge – assuming your audience possesses the same knowledge and vocabulary as you. We saw this during Covid when public health officials spoke about "pathogenic variants" and "congregate settings" instead of using plain language that everyone could understand. Even President Obama sometimes fell victim to verbosity, speaking about "international rules and norms" when many listeners might not know what a "norm" is. The solution is simple: Talk Like a Human. Follow what I call the BBQ Rule – if you wouldn't say it at a barbecue with your family and friends, don't say it in a speech. At a BBQ, you might be talking with your grandma, your crazy uncle, or your thirteen-year-old niece – or all of them at once. You wouldn't say, "I utilize next-generation innovations to create synergies that optimize technology for positive health outcomes." You'd say, "We make watches that monitor your heart rate and share that information with your doctor so you can stay healthy." When Ellen Moy started a nonprofit called The Clothesline for Arlington Kids to provide free clothing to children in need, she initially described her work in clinical terms – focusing on "the business model" and "the process." Working together, we reimagined her message to emphasize how she offers a "welcoming, fun, retail-like setting" for children to pick out "a season's worth of quality clothing," and how her organization "represents Arlington at our best – neighbors helping neighbors." Most importantly, Ellen started telling a bigger, more human story: "This is about more than giving a child a coat or a pair of shoes. It's about kids feeling comfortable going to school so they can learn. It's about dignity." Clear language isn't just about being understood—it's about honoring the humanity of our listeners. When we strip away jargon and speak with simplicity and warmth, we create space for genuine connection. The most powerful communication happens not when we impress others with our vocabulary or expertise, but when we meet them where they are with words that welcome rather than exclude. In a world increasingly dominated by technical language and specialized knowledge, the ability to speak with clarity and humanity becomes not just a skill but an act of compassion.

Chapter 6: Truth and Values: Building Trust in a Post-Truth World

In his final year in office, President Obama had grown frustrated with Donald Trump's repeated criticism that he wouldn't use the phrase "radical Islamic terrorism" to describe ISIS. After a gunman who had pledged allegiance to ISIS massacred forty-nine people at Pulse nightclub in Orlando, Trump tweeted: "Appreciate the congrats on being right on radical Islamic terrorism." Two days later, Obama was scheduled to deliver an update on the fight against ISIS. When I retrieved his edits, I saw he had written an entire page explaining why he avoided such inflammatory language. At the podium, Obama explained that "groups like ISIS and al Qaeda want to make this war a war between Islam and America. That's their propaganda. That's how they recruit. And if we fall into the trap of painting all Muslims with a broad brush... then we're doing the terrorists' work for them." What struck me most was a note Obama had written at the top of the draft: "Terry—make sure I'm precise in describing what Trump has already proposed." Even as he was excoriating a political opponent, Obama was determined to be accurate. Even in anger, he wanted to tell the truth. This commitment to truth matters more than ever in our "post-truth" world, where politicians dismiss criticism as "fake news" and offer "alternative facts." Social media and AI accelerate the spread of misinformation. Studies show that lies often travel faster than truth – in one MIT study, researchers found that "falsehood diffused significantly farther, faster, deeper, and more broadly than the truth" on Twitter. The consequences of lies can be devastating. Lies about the Vietnam War contributed to the deaths of thousands of Americans and millions across Southeast Asia. The lie that the 2020 election was "rigged" led to the January 6 attack on the Capitol. Every time we speak, we have a choice: stick to facts or spread falsehoods, uphold trust or erode it. When you speak, tell the truth. This means avoiding plagiarism, not making things up, getting your facts right, and verifying sources. As Alexandra Platkin, who led the White House research team at the end of Obama's presidency, put it: "Lying is bad. It's also stupid." Your credibility is your most precious asset as a speaker – once lost, it's nearly impossible to regain. In an era where truth itself seems under assault, the commitment to honest communication becomes not just a personal virtue but a social responsibility. When we speak truthfully—even when it's difficult or inconvenient—we create islands of trust in a sea of manipulation. The most influential communicators understand that their power comes not from clever rhetoric or emotional appeals, but from the foundation of credibility built through consistent truthfulness. By anchoring our words in verifiable facts and authentic values, we offer something increasingly rare and precious: communication worthy of trust.

Chapter 7: The Art of Performance: Creating Memorable Experiences

One of the first speeches I ever worked on for President Obama was nearly a disaster. He was set to announce recommendations from a major review of the country's cyber defenses. I drafted the speech, but when it came back from policy experts, they had crossed out almost everything I'd written and replaced it with dense, technical language like: "cyberspace is the interdependent network of information technology infrastructures, and includes the internet, telecommunications networks, computer systems, and embedded processors and controllers in critical industries." In a panic, I called Ben Rhodes, Obama's chief foreign policy speechwriter. "Don't worry about it," he said. "Just write what you think Obama should say." Of course – what the president should say. Obama would have to stand up and deliver every line I drafted. He'd have to pronounce every word. And his remarks had to be clear to the people in the audience who were listening. This experience taught me an essential truth: a speech is not an essay, a white paper, a press release, or a book. A speech is a performance – like a play. It has a setting, staging, an entrance, a script, and most importantly, an audience. A speech is meant to be heard, not read. Your audience won't have a copy of your script in their hands. If they don't understand something, they can't go back and check what they missed. Every word must be absolutely clear – to the ear. Understanding that a speech is a performance can be liberating. You have more control over the experience than you realize, including the ability to deliver a performance that only you can deliver. The Golden Rule of Public Speaking is simple: be yourself. Speak in a way that sounds natural to you. Donovan Livingston demonstrated this perfectly when he was selected to speak at his Harvard Graduate School of Education convocation. Instead of giving a conventional speech, he delivered a spoken-word poem that reflected his identity as a hip-hop artist. "I wanted to make sure that I did him justice," Donovan said of civil rights icon John Lewis, whom he'd once introduced. He prepared meticulously, writing at his kitchen table while listening to Chance the Rapper for inspiration, and rehearsed "maybe a hundred times" in front of his bathroom mirror. Taking the podium in his black suit with a multicolored kente stole representing his pride in being a Black graduate, Donovan immediately engaged his audience: "Good afternoon, good afternoon. How's everyone doing today?" He encouraged participation: "snap, clap, throw up your hands, rejoice, celebrate." As he performed, he shifted between his feet, his body moving with the rhythm of his words, the audience matching his energy with cheers and hollers of approval. The most powerful presentations transcend mere information delivery to create experiences that resonate long after the final words are spoken. When we approach speaking as a performance—not in the sense of artifice but of intentional creation—we transform ordinary moments into extraordinary connections. This doesn't mean becoming someone you're not; rather, it means bringing your full, authentic self to each speaking opportunity with thoughtful preparation and purposeful delivery. The speakers we remember aren't those who merely informed us, but those who moved us, challenged us, and made us feel something meaningful through the artful integration of words, presence, and passion.

Summary

Finding your authentic voice is perhaps life's most profound journey—a path that leads not just to better communication but to deeper self-knowledge and more meaningful connection with others. Through the stories of world leaders and everyday communicators alike, we discover that powerful speaking emerges not from technical perfection but from the courage to be genuinely ourselves. When we prepare thoughtfully, speak from the heart, use clear human language, honor truth, and approach each opportunity as a performance worthy of our audience's attention, we transform not just how others hear us, but how we experience ourselves. The journey from trembling novice to confident communicator isn't about eliminating fear or mastering tricks—it's about discovering the unique contribution only you can make. Your voice matters not because it's flawless, but because it's yours. As you step forward to speak, remember that your greatest authority comes not from your title or expertise, but from your willingness to share your authentic self. In a world hungry for genuine connection, there is no greater gift than the courage to speak your truth with clarity, compassion, and conviction. Your voice, in all its beautiful imperfection, is exactly what someone needs to hear.

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Review Summary

Strengths: The book offers numerous tips on writing and delivering speeches, making it potentially valuable for those interested in improving public speaking skills. It includes insights from Terry Szuplat's experience as a speechwriter for Obama, providing a unique perspective.\nWeaknesses: The target audience is unclear, as the book is written for the general public, but not many people give speeches regularly. The reviewer also expresses a lack of interest in memoirs or works that capitalize on time spent with a president.\nOverall Sentiment: Mixed\nKey Takeaway: While the book may not appeal to everyone, particularly those uninterested in public speaking or political memoirs, it could be beneficial for individuals looking to enhance their public speaking abilities through the lens of a former presidential speechwriter's experiences.

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Terry Szuplat

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Say It Well

By Terry Szuplat

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