Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

CHAPTER 13

I’M GLAD I ASKED

I EMBARKED ON THIS project to discover a better and more disciplined way to ask questions. I wanted to find out if questioning could be organized around specific objectives and how the types of questions we ask affect how we listen. Though I had asked questions all my life as a journalist and interviewer, I never thought of them as “strategic” or “creative” or “empathetic.” I didn’t build inquiry around outcomes. But as I talked to close to 100 people for this book, curious souls skilled at turning questions into discovery and results, I became convinced that a “taxonomy” of questions, each with its own approach and compelling benefits, could serve as a useful way to think about what and how we ask. I don’t pretend that my way of approaching questions is definitive; some of the best inquiry is generated by random curiosity. But by understanding what we’re asking, how we listen, and when we should ask more, we can become better questioners with tangible results to show for it.

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Still, we must appreciate that questions are not a blank check. There is such a thing as a stupid question. I’ve heard plenty of them over the years. Stupid questions reveal willful ignorance, laziness, or a painful lack of preparation. There are also hurtful questions that humiliate or open old wounds. Gratuitously hostile questions—meant to embarrass or pick a fight—can poison a conversation. Inappropriately personal queries can get you in trouble. Self-serving questions, where someone asks a question just to show off how much he or she really knows, turn off everyone else.

Cultural sensitivities vary widely; one person’s question may be another’s insult. Some cultures defer to age and authority or view public questioning as inappropriate or disrespectful.

A few years ago, while teaching a university class in China, I employed what I thought was some good, provocative Socratic questioning about what the United States and China were up to in the world and how the students perceived the competition. I challenged the students to share their opinions, define their terms, and support their views. A Chinese student leaned over to one of the Americans in the room and asked, “What is he doing, trying to get us to fight?” This was unfamiliar, uncomfortable territory for these students and my questions landed with a thud.

In some societies, questions are viewed as an outright threat. Repressive regimes know they cannot stand up to scrutiny or challenge. Thought dictatorships reject accountability and suppress curiosity.

A “Letter from Pyongyang” in the Washington Post caught my eye. Entitled “Virtual Reality Inside North Korea,” the article by Anna Fifield told the story of her tour of a North Korean hospital with a group of reporters. A secretive, brutally repressive state, North Korea wanted to show off healthcare in the communist paradise. The tour was surreal. Fifield saw “decades-old” incubators in the maternity ward and a lab stocked with “a museum exhibit of scientific instruments.” She asked one of the doctors who was assigned to the group whether international sanctions “limited your ability to get the technology you need to do your work.”

Sanctions had caused suffering, came the answer, but “Great Leader Marshal Kim Jong-un taught us to learn about technology and science so we have the ability to develop by ourselves.”

Later in the tour, Fifield asked if the doctor had access to the internet. He went to a nearby building to go online three or four times a week, he replied. Had he been online this past week? “No, no times this week.”

As they passed a CT scanner, Fifield asked if they could turn it on so she could see it work. The response: “Why? Do you have a serious health problem?” she was asked.

“You ask too many questions,” Fifield’s government minder told her. “It’s a little hard to work with you.”

In North Korea, there’s no point and little future in asking.

In vibrant societies, however, we want our next generation of questioners to be better than the last. Indeed, the people I spoke with for this book know that the ability to ask is directly connected to our ability to invent and innovate, to push boundaries and pose the big questions that confront us as a society. Some have dedicated themselves to teaching young people and helping future generations understand the power and poetry of questions. Three such individuals stood out for their commitment to the future.

The Justice of Citizenship

Justice Sandra Day O’Connor asked some of the biggest questions confronting America during her twenty-five years on the United States Supreme Court. Though she had been retired for several years, she still kept an office deep inside the massive neoclassical building. Justice O’Connor was in her eighties. A cane leaned against her desk. But her voice was strong and clear as she rose without effort to greet me.

We weren’t there to discuss her opinions in some of the most significant cases in American history—not Bush v. Gore, when the Court (with her crucial vote) picked a president; nor Planned Parenthood v. Casey, when she sided with the liberal justices upholding Roe v. Wade. “I don’t look back,” she told me definitively. “That’s for a historian or a book writer. I did the best I could and that’s that.”

We were there to talk instead about her initiative to teach young people about the important questions of government and citizenship. Sitting in her cavernous office, wrapped with shelves heavy with books on law and government, it was impossible not to feel the weight of history and the great debates that had defined America. The American experience, Justice O’Connor explained, was built on defining questions.

Are we going to be a nation?

If so, what form of government are we going to choose?

And how will the people be part of resolving it?

On July 2, 1776, the Second Continental Congress voted to declare independence from Great Britain and its tyrannical king. The next day John Adams, in one of his famous letters to his wife, Abigail, wrote, “Yesterday, the greatest question was decided, which ever was debated in America, and a greater, perhaps, never was nor will be decided among men.” From there, a nation of ideas evolved.

Some 240 years later, O’Connor was worried. We were losing our sense of history, civics, and our understanding of these big questions, she feared. Our schools were failing us. As a parent, years earlier, she had been struck by how little time her children and their friends spent studying how government worked. It had only gotten worse. She felt young people urgently needed to learn what “citizens have to do and decide” if they were to participate in the world around them.

The words hit me hard in this place, especially as I considered the polarizing, paralyzing debate that passed for political discourse outside. Benjamin Franklin had said, “It is the first responsibility of every citizen to question authority.” But citizens need to know whom to question and how, if they are to do it effectively.

Motivated by the conviction that citizens must understand the basics of government if they are to question and change it, O’Connor started iCivics, an online teaching tool that uses games and interactive exercises to help young people learn how government works and how they can be part of the process. At the time we spoke, more than 100,000 teachers and 3 million students had visited iCivics, playing its educational video games more than 10 million times.

O’Connor wanted future generations to understand and to engage America’s foundational questions:

What is the role of government?

How do we balance individual liberty with social responsibility?

What does responsible citizenship entail?

Justice O’Connor seemed as proud of her iCivics initiative as her years on the bench. Hers was an astonishing career. She broke virtually every barrier that got in her way. She made history in her own right as the first woman to serve on the Supreme Court. But helping young people appreciate the American experiment and what it asks of them as citizens was a mission that lit her up.

“I think we’ve achieved something,” she told me modestly.

Ask to Lead

Debbie Bial is passionate in her belief that young people who ask the next generation’s questions will be its leaders. Debbie founded and runs The Posse Foundation, an organization that identifies extraordinary high school students based on their talents and leadership potential. Mostly from inner cities, the “Posse scholars” are paired with colleges and universities that provide full tuition. The groups of students that go to these schools are known as Posses. They are the most engaged, motivated, and diverse kids you could ever meet. When they get to campus, many take on leadership roles or start new student organizations. Most are the first in their families to go to college. I have worked with Posse scholars for years and served on the Posse Board. I’m a true believer.

The Posse recruitment and selection process is structured around stimulating and often intensely reflective questions. Debbie builds communication skills and leadership qualities into the scholars’ experience by constantly asking them about themselves and the world around them. At student gatherings, board meetings, and staff retreats, Debbie uses question exercises as “catalysts for dialogue.” She shows participants pictures or news stories about a topic that cuts close to home—race, class, climate, the election—and asks:

When you think about this, how does it affect or influence your everyday life?

How does it affect your job?

Where are you in this story?

She asks a roomful of people to form two lines facing each other. Everyone gets a question and has sixty seconds to answer.

What labels do you use to describe yourself, or do you use no labels?

Are your labels different from labels others use?

What’s the greatest risk you’ve ever taken?

She asks a group to sit in a circle.

What’s the hardest thing you’ve ever experienced?

If you were to sit down for lunch with your nineteen-year-old self, who would you see?

What percentage of you is your dark side?

“We create a structured framework around the question,” Debbie explained, in order to build relationships, provoke conversation, develop leadership, and create bridges between communities. At a time of increasing diversity in America, and as everything seems to get more complex, Debbie argues that leadership starts with an ability to ask and to listen, to bridge differences and build community. She’s betting the future on it.

“The question as a tool is the core of everything we do,” she says.

Poems of Humanity

David Isay, like Debbie Bial and Sandra Day O’Connor, is also investing in the future. Isay is creator of StoryCorps, a project that millions of listeners hear on podcasts, NPR, and online. StoryCorps invites ordinary citizens to interview one another. Parents, children, husbands, wives, friends, and partners produce remarkable conversations that evoke a rich and enduring spoken mosaic of American life. StoryCorp’s declares that its mission is to “preserve and share humanity’s stories in order to build connections between people and create a more just and compassionate world.”

Forty-minute interviews get edited to three minutes. Each interview is intensely personal in its own way: A mother forgives the man who murdered her son and says she hopes to see him graduate from college; a military veteran asks his wife “What made you stick around?” as he wrestled with rage and alcohol driven by his post-traumatic stress disorder (PTSD); a man with Down syndrome answers his mother’s questions about growing up with a curse he now calls a gift.

The appointment with a microphone, Isay told me, creates time and license to ask about subjects that normally get buried or dismissed. StoryCorps offers a list of “Great Questions” to get the conversations started.

What was the happiest moment of your life?

Was there a time when you didn’t like me?

What makes us such good friends?

StoryCorps interviews are archived at the American Folklife Center at the Library of Congress, allowing participants to leave a legacy for future generations.

Isay told me that many of these conversations become “poems of humanity.” He’s right. Each story speaks in its distinct cadence, offering a unique journey to an individual’s life story. The poetry happens because someone asked.

Always Asking

It was inspiring to hear from these people who work so hard to advance the culture of curiosity. It is a message educators try to convey to students every chance we get: A successful education is one that only gets you started. It’s not the questions you’ve answered, but the ones you have yet to ask that will lead to discovery, ensure your place in the world, and help you succeed at a time of rapid change.

I tried to do my part over the years and when my kids were young, though I encountered some predictable resistance. I had a reputation for mealtime interviewing. I asked about school, homework, sports, friends, weekend plans—all the activities that kids are into and parents want to know about. I thought I was being a good dad, projecting my interest in my kids and their friends, encouraging them to tell stories and share with the family. But my questions could cause fifteen-year-old eyes to roll. My son would say, “Dad, it’s dinnertime. Stop being a reporter.” I defended myself, of course, and asked again.

What was one new thing you learned in school today?

If you could visit any time and place in history, where would you go?

What’s the book about?

Who is your favorite teacher? Why?

Who do you confide in when you are confused?

My son Chris recalled that “as kids, we used to joke that Dad could ask the same questions in thirty different ways.”

As the kids got older, my questions grew up too.

Does money matter?

How much is too much?

Is there something you believe in so strongly that you would give your life for it?

How do you know if you have had a successful life?

While my household interviewing became a family joke, my kids did answer my questions most of the time. Now that they are grown, they still trot out the “Dad’s playing reporter” line when it fits, and we all have a good laugh. Sure, I overdid it at times, and I realize a fine line exists between asking enough and asking too much, between showing interest and prying. That’s why listening is so important. It not only helps you learn, it also helps you shut up. But I’m glad I asked all those questions. My curiosity in their lives reflected both my interest in their present and my investment in their future. I’m pretty sure they’ll grill their kids someday, too.

My life has been enriched at every stage by the opportunities I’ve had to question. I have been invited into people’s lives and adventures, taken on fascinating journeys because I’ve had license to ask more. Different places and different audiences have afforded distinct opportunities.

For years, I hosted CNN’s Sunday morning talk show. Each week, I questioned prominent people and dove into the issues, triumphs, setbacks, and controversies that had made headlines. I questioned the Israeli prime minister in the midst of crisis. I spoke with the CIA director as he walked me around the agency to show a slice of how they tracked the world. I asked medical experts about the latest global health crisis. It was the hard news, the front page of cable news, driven by questions that explained the story.

At The George Washington University, I started the Conversation Series, a more informal discussion with public figures in front of a live audience. My questions there revolved around the guests’ accomplishments, their views of public life and their explanations for the positions they took. With my next-generation crowd in mind, I asked how my guests got started and what they recommended to young people who wanted to make their mark. I came to think of these interviews as conversations with the future.

On NPR, I had the pleasure occasionally to host the Diane Rehm Show. Diane captained her very smart show for more than thirty-five years. Her story is richly ironic. Growing up in Washington DC in an Arab household, Diane was not allowed to question her parents or much else in her life. Such behavior was considered disrespectful. Yet she became one of the great interviewers, demonstrating that radio is a magical and intimate medium. Sitting in for Diane, I had a chance to interview a fabulous range of people, from bestselling authors like Jane Goodall and Nicholas Kristof, to experts too obscure for cable TV but ideally suited to insightful conversation on public radio. The questions here embraced complexity.

I will always be grateful to the people over the years who answered my questions, humoring my ignorance, feeding my curiosity, allowing me to hold them to account. They were my tour guides through ideas, history, and great human events that I never would have experienced otherwise. They told compelling stories as they went. I could ask anything, go anywhere.

But for all my experience asking and listening, I didn’t appreciate how much more there was to learn about the discipline of inquiry until I tackled this book. The people who talked to me patiently explained how they worked, how they framed their questions, and what they listened for. Each one of them showed me how asking more, in a more disciplined way, could lead to tangible results and deeper understanding. They, too, used their questions to invest in the future.

Simone, my student whose experience encouraged me to launch this project, learned her family secret because she had an assignment to ask. She realized a deeper relationship with her father as a result.

Barry Spodak put his troubled human puzzles together by taking time to slowly build bridges. His work helped the people trying to keep us safe.

Jim Davis built his business by asking for team players, listening for “we” not “I.” His company, New Balance, is global but still makes shoes in America.

Rick Leach enlisted people to take on the daunting challenge of feeding the world by asking them to share a vision: Hunger is a solvable problem.

Tony Fauci, who knew his quest would never end, pushed the bounds of science to take on disease. His questions drove research that saved lives.

Ed Bernero and Gavin Newsom used questions to push people into an imagined reality where they could think differently and imagine a different world.

Terry Gross and Betty Pristera asked people to reveal the essence of themselves. They walked in other people’s shoes and discovered new places as a result.

Anderson Cooper and Jorge Ramos demanded explanation. They confronted their adversaries with the most challenging questions so that everyone could see and judge.

Chris Schroeder’s recipe for dinnertime conversation and brilliant entertaining questions forged new ideas and friendships.

General Colin Powell started with an “estimate of the situation” and used strategic questioning to determine whether the situation was worthy of the investment. He saw that strategic questions must challenge conventional wisdom and groupthink.

Nurse practitioner Teresa Gardner and roofer Al Darby became experts in asking, “What’s wrong?” They knew they couldn’t fix a problem if they couldn’t identify its source.

Rabbi Gary Fink answered a question with a question, prompting a conversation that would provide comfort and meaning at life’s most challenging time.

Profane and Profound

Although the roadmap to inquiry I’ve drawn can help us navigate with a more deliberate eye, there are always alternate routes—scenic drives that take us to unexpected destinations. Questions that spring from pure curiosity can turn into gold. Unplanned detours can lead to serendipity, as I also found during the interviews for this book. One such conversation left me speechless, and I will end by sharing it with you.

As I was talking with Dr. Anthony Fauci at the National Institutes of Health about scientific inquiry and how it could be useful to nonscientists, something was gnawing at me. In his discussion about research in the early days of AIDS, Fauci spoke about the work, about the research and the discoveries, about patients and process. His observations were fascinating, and not without feeling. But he sounded, well, like a scientist—captivated by his research and his breakthroughs and setbacks. Yet Fauci had a perspective almost no one could imagine and I wondered: What was it like for him in those days, caught in the middle of the colliding worlds of medicine, culture, and politics, to see such human suffering? I recalled the headlines from the time, which revealed ignorance, fear and bigotry. I interrupted our science discussion to ask:

Did you ever wonder how can this be happening out there and ask yourself, can I make them see what I am seeing?

Suddenly, this man of science fell silent. His lips trembled and his eyes filled with tears. Finally he spoke. “I am actually laughing and crying at the same time,” he said. “I have a lot of suppressed feelings from back then.”

He paused and gathered himself. And then he slowly erupted.

“The answer to your question is yes. There was a lot of, you know, ‘What the fuck is going on here?’”

Another pause.

“It was not easy when you see everybody die. So I need to say this in a way without getting more emotional about it. There were multiple years, from 1981 to 1986, where you wanted to keep a positive outlook. But everybody died. Everybody died …”

He wiped his tears.

“That was probably one of the things that gave me the phenomenal energy to get solutions. People say, ‘How come you didn’t burn out? You know, thirty-three years and you kept on doing your work for seventeen, eighteen hours a day.’ It was that kind of realization that this was an enormous problem.”

He leaned forward and spoke deliberately, emphatically.

“And the thing that was, I guess, a little bit different was there was something about—and I want to make sure I say it accurately—there was something about the young gay population that was, I think, particularly tragic. Because most of the time—and you never made judgments about your patients and their personality—but in general, as a demographic group, they were gentle, artistic, kind. There were very few assholes among them. There were a lot of good, gentle people who were scared shitless. And for those years, they came in and there really wasn’t a lot you could do for them …

“It was very painful and very frustrating, and the thing that got me to have this response is—you are right, there was a lot of bullshit going on in the outside. Not giving them insurance, throwing them out of their houses. And you think what a shit world we live in.

“It is interesting that you ask that question,” he said to me. “I have not had an emotional response to this in twenty-five years.”

Perhaps I looked away at that moment.

“Sorry. No,” he said. “It’s fine and it’s cathartic.”

Fauci’s comments sprang from his gut, raw and profane, triggered by a single question that had nothing to do with the scientific method. He shared his passion. He took me to the roots of his emotions and displayed his rage and his frustration and his humanity. I felt privileged to have experienced the intensity of this remarkable man. It was like stepping to the edge of a volcano and peering over it to see the molten lava and feel the heat.

This book is dedicated to the curiosity and passion in us all. Questions are humanity’s unique attribute. They are our investment in ourselves and in the future. When we ask more, we open our minds and challenge others to open theirs. We organize our thoughts so we can tackle big ideas and probe with precision. We learn and lead and discover.

Questions are our way to connect with other human beings. I believe that inquiry, not imitation, I believe that inquiry is the sincerest form of flattery. Ask a good question and you convey interest. Slow down, listen closely, and ask more and you engage at a deeper level. You show that you care. You generate trust. You empathize and you bridge differences. You become a better friend, colleague, innovator, citizen, leader, or family member. You shape the future.

You can’t ask for more than that.