CHAPTER 1
WHY ASK?
SMART QUESTIONS MAKE SMARTER PEOPLE. We learn, connect, observe, and invent through the questions we ask. We push boundaries and we discover secrets. We solve mysteries and we imagine new ways of doing things. We ponder our purpose and we set our sights. We hold people accountable. We live generously, to paraphrase John F. Kennedy, by asking not what others can do for us, but what we can do for them. Curiosity opens our minds and captivates our imaginations.
But the fact is, most of us don’t really understand how questions work—or how to make them work for us. In school we study math and science, literature and history. At work we learn about outcomes and metrics, profit and loss. But never do we study how to ask questions strategically, how to listen actively, or how to use questions as a powerful tool toward accomplishing what we really want to achieve.
Questions—asked the right way, under the right circumstances—can help you achieve both short-term and lifelong goals. They can open doors to discovery and success, bring you closer to a loved one, and even uncover answers to the universe’s most enduring mysteries. Insightful questions help you connect with a stranger, impress a job interviewer, or entertain at your next dinner party, and they can be the keys to a happier, more productive, and fulfilling life.
This book shows you what you get when you ask for it. In each chapter I explore a different type of question, driven by its own approach and listening skills. By the end of the book, you’ll be able to recognize what to ask and when, what you should listen for, and what you can expect as the outcome. Each chapter offers stories and looks at the genre through remarkable people who have used questions to motivate and excel.
For nearly four decades it’s been my job to ask questions. From an inner-city school to a technology revolution, from the Brandenburg Gate where a president said, “Mr. Gorbachev, tear down this wall!” to the inauguration of the first African-American president, I have had the privilege of being there—watching, listening, and asking. I’ve interviewed world leaders who shaped history and heroes who dedicated themselves to the poor and the disabled. I’ve questioned avowed racists and the richest man in the world. As a journalist and interviewer, I have been enriched by these experiences and privileged to share them publicly—on CNN, NPR, and other media, and in front of live audiences. Now I teach college students how to ask to get information, to find the facts, to hold the powerful to account, and to create revealing moments for the world to see.
As my fascination with inquiry has grown, I’ve become increasingly alarmed about the questions we ask—or don’t ask—in public and daily life. Technology has revealed endless horizons, but it has also created a quick-hit, search-engine culture where a fast answer can obscure deeper inquiry. The polarization of politics, amplified by social media, has fractured civic discourse and infused it with invective instead of dialogue. The news media, reflecting and reinforcing these trends, have grown shorter and sharper. Compared to when I got into the business, television interviewers are given less time and focus more on controversy and horse race than on explanation and substance. Sincere questions too often play second fiddle to certainty, ideology, and outrage. But what if we asked more and asserted less? What would we discover? How much better would we understand the people around us? What if we went asking for solutions and posed truly creative questions that could change the world?
A student convinced me I should write this book.
Simone (I’ve changed her name) had arranged to interview her father—I’ll call him Morley—for an assignment I had given my Art of the Interview class. A devoted family man, Morley kept his emotions to himself and was not prone to reflection. At first he refused. “Go find someone else,” he told his daughter. But Simone persisted, and finally her father agreed to the interview, camera and all.
Simone had questions she always wanted to ask. Morley had issues he never wanted to discuss. They sat facing each other in the den, a place both of them knew well. Simone started with some innocuous open-ended questions, a classic interviewing technique. She asked about her father’s college days and how he met his wife, Simone’s mother. When Morley seemed more relaxed, Simone asked the question she’d been thinking about for a long time.
“Before I was born a child passed away,” she said. “Can you tell me what happened?” For more than twenty years, the family had faithfully commemorated the child’s birthday, but they had never really talked about what happened.
“She was born premature,” Morley said. “She lived for about a day and a half. Her lungs hadn’t fully formed. That created a series of other problems.” He paused. Then came the secret he’d never told anyone, not even his own parents.
“Your mom and I decided that we would disconnect her from life support.” His voice trailed off. He swallowed hard, trying to stay in control.
Simone kept going. “Was it a difficult decision? How did you and mom handle that?” Her father teared up. So did she.
Morley’s words came slowly. “At the time it was very hard . . . It was probably hardest to see some of our friends with kids at that time.” Another pause. “But those experiences shape you.” He looked at his daughter. He saw a beautiful and smart young woman—his legacy and his love. Still emotional, Morley told her she wouldn’t be alive if that terrible event had not occurred.
Simone’s head was spinning. To learn the details was difficult enough, but to see her strong, unshakable father so upset revealed a vulnerability she had never seen.
“I understand now, after what he had been through, why I meant so much to him,” she told me later. “I understand why he has always made such an effort to spend time with me, to be there for important events in my life, to tell me how proud he is of me. Now when he gives me a hug I don’t pull away as quickly. When I miss his call I make sure to try him back right away.”
Simone uncovered a deep secret, discovered a different side of her dad, and changed the way she related to her father simply because she asked. More, much more, than an oral history came from her questions.
And so I began to explore the power of questions in their different forms.
I talked to dozens of people, master questioners if you will, to understand how they used questions in their lives and professions and to see what we could learn from them. The inquiry teachers in this book comprise some of the most fascinating and successful people I’ve met, some famous and some not so famous. The arc of their lives has been assisted by their ability to question the people and the world around them.
The book begins with a problem. If you’ve ever confronted something that’s gone wrong, with time running out, you know that asking the right questions can make the difference between a good call and a catastrophic mistake. Chapter 2 introduces you to people who diagnose problems for a living: a nurse-practitioner in Appalachia, a renowned corporate turnaround artist, and my neighbor, the roofer. They’re all experts at asking questions to pinpoint a problem so they can fix it. You’ll see how you can zero in, listen hard, and draw on experience and instinct.
Chapter 3, “The General’s Charge,” shows you how to stand back and think big when the stakes are high and the outcome is unclear. Strategic questions ask about choices, risks, and consequences. They force you to challenge conventional wisdom and your own biases. They lead to better, clearer thinking and better planning when you’re weighing big decisions. As General Colin Powell explained to me, great strategic questions can inform the hardest decisions, just as failing to ask the right questions can lead to disaster.
If you want to connect with someone, you will see how the experts do it as you read Chapter 4, “From the Inside Out.” Empathetic questions can bring you closer to people you know or have just met. These questions help you become a better friend, colleague, partner, or family member. They lead to deeper understanding and discovery. You’ll hear from a family therapist, a Harvard professor who teaches empathy, and from one of the best interviewers in America, NPR’s Terry Gross.
Want to know a secret, maybe a dangerous one? In Chapter 5 you’ll learn how careful, patient questioning can build a bridge to someone who doesn’t want to talk to you. These bridging questions reach out to people who are wary, distrustful, and even hostile. You’ll see how an expert in Dangerous Threat Assessment uses them to solve difficult, and sometimes volatile, human puzzles. He asks questions without question marks. Understanding how this is done will help you communicate, if not with terrorists, then at least with teenagers.
And if no bridge can be built? Chapter 6 will show you how you can use confrontational questions to hold people accountable for what they’ve done or said. While this kind of inquiry is often unpleasant, as I once discovered in a bizarre encounter, it does establish a record. Know what you’re after, as Anderson Cooper explains. Be prepared for the consequences, as Jorge Ramos recounts. But as you will see, if you have the courage of your convictions, know what you’re talking about, and can ask with precision, you can be a more formidable adversary.
How many times have you heard that you should think outside the box, be original, and take a chance? In Chapter 7 you’ll realize you can get there through questions, not commands. If you want to get creative juices really flowing, ask people to imagine, to set their sights high, to pretend gravity doesn’t exist. What do California Lieutenant Governor and former San Francisco Mayor Gavin Newsom and Hollywood television series creator Ed Bernero have in common? They both use questions to transport people to a place where they cannot fail.
In Chapter 8, “The Solvable Problem,” you’ll see how you can create a sense of purpose and mission through your questions and inspire people to pitch in, or maybe even write a check. You’ll meet Karen Osborne, who has raised millions of dollars, and Rick Leach, who wants to feed the world. You can borrow from their approach to become your own pied piper. You’ll discover surprising ways to improve listening, set common goals, and take concrete action.
Chapter 9 ventures into the unknown and the unexplained to see how scientific questions can solve the mysteries of the world. You will meet the doctor-researcher who threw himself at HIV/AIDS and Ebola when people were dying and the public was in panic. You’ll also find inspiration and ideas you can apply in your own life.
Next come the money questions. You’re trying to fill a job. You want the job. What you ask tests your compatibility and, just maybe, predicts the future. Chapter 10 shows you how these questions get asked—from both sides. You’ll meet a CEO who goes for the team approach and a technology veteran who just might ask about your favorite aisle in the supermarket.
Entertaining questions can turn your boring dinner into a theater of wit and ideas and provocative conversation. Be your own talk show host. In Chapter 11, you’ll learn ways to draw out memorable dialogue and keep the conversation moving, using ideas from one of the most engaging and curious people I’ve ever met. Invite Socrates to supper—if you dare. Serve this recipe at your next meal and you’ll have everyone talking.
Finally, what does it all mean? Chapter 12 asks legacy questions that reveal your life story and craft an uplifting narrative of accomplishment and gratitude. These questions from the edge will help you step back and take stock of what you have done and the people you have known. Here, you meet the rabbi who gets asked about God’s intentions and read the curious words of a twenty-five-year-old who questions her future. I introduce you to one of the bravest people I’ve ever met.
At the back of the book, I provide a guide that summarizes the question categories and their component parts, with a few ideas you can try to become a more effective questioner.
This book is not prescriptive. It doesn’t tell you how to ask in every situation. But it does offer examples that demonstrate the power of questions and the benefits of deep, nuanced listening. The categories reflect a range of curiosity. As you will see, each enlists different asking skills in search of distinct outcomes. Humans are built to be curious, that much is in our DNA. This book illustrates how some of the most successful people have honed their curiosity and developed an ability to ask and to listen that has served them extraordinarily well.
Our questions reflect who we are, where we go, and how we connect. They help us learn and they help us lead because effective questioning marshals support and enlists others to join. After all, asking people to solve a problem or come up with a new idea turns the responsibility over to them. It says, “You’re smart, you’re valuable, you know what you’re doing—what would you do about this problem?”
My aim in writing this book is to show you the power of questions and how it can be applied effectively and freely. Enjoy and learn from the exceptional questioners you meet here.
And then, ask more.