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

CHAPTER 11

THE INSPIRED HOST

Entertaining Questions

BEING A TALK-SHOW HOST IS FUN. You meet interesting people. You get to ask them about their work and their lives, probe their past, and ask them to tell stories. You push them and get personal, test their mettle, and find the funny. You can go for the reflective and thoughtful, or you can be tough and demanding, asking why your guest did what she did when she did it. It’s your call because it’s your show. You set the agenda. You own the space.

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But even if you don’t have a show or will never get near a camera, you can be a host who deftly steers conversation, draws in the guests, energizes an audience. You can do it over dinner, at work, in your social life, or with friends. You can set the agenda and create a mood that serves up ideas and connects people in stimulating, and surprising ways. You can become the maestro whose questions find the high notes that create an invigorating experience that wins rave reviews.

Entertaining questions allow you to engage your audience and keep the conversation interesting and lively so everyone plays. You can be commanding or charming, funny or unpredictable, but the objective always revolves around creating an experience that your guests will enjoy and remember. Use questions the same way a chef uses spices: subtly but deliberately to bring out the flavors of the meal. Basic ingredients?

Know your audience. Who you are talking to? What have they done? Where have they been and what do they care about? Pick questions that intrigue and interest everyone.

Think creatively, choose deliberately. Draw from a menu of topics and questions to create flow and distinctive moments. Sports or politics, fishing or sailing, it’s up to you, but you want a combination of topics that will engage different people on different levels. It’s like the meal: plates filled with flavors and colors, veggies and proteins.

Set a mood and set a rhythm. Funny or serious? Provocative or reflective? Set the mood through signals, prompts, words, and timing.

Engage emotion. You trigger emotions through the subjects you pick and the questions you ask. Serious or snide? Funny or flippant? Your call.

I find that if I start with an exchange that is spontaneous and a little unexpected, I can often break the ice, get a smile, and set a tone that is more relaxed and will lead to a more genuine experience.

I was hosting one of my Conversation Series events at The George Washington University, onstage with House Minority Leader and former House Speaker Nancy Pelosi. I had interviewed Pelosi before and knew her reasonably well. I had a bunch of things I wanted to ask her about—politics, the economy, climate change, Washington’s weird ways. In doing my research, I had been warned, very diplomatically, that Pelosi was prone to long, sometimes slightly meandering answers. I didn’t want that. I was looking for a genuine conversation that would cover a lot of ground and illuminate both her politics and her personality. I wanted to draw her out on the polarization in the country and what she could do to change that. I wanted her to talk about how (and why) anyone would go into politics. Mostly, though, I wanted her to engage in a spontaneous and conversational way with me and with the audience.

I decided to start by asking if she’d be willing to begin with a little game.

She looked at me quizzically. “Whatever you wish,” she said warily.

Okay, I said, “I’ll give you a name or a topic, you get a one-word response.”

“Do I get the same?” she asked with a grin.

“Absolutely!” I responded. The audience laughed in anticipation.

Pelosi leaned forward, watching intently, not knowing exactly where this was going. I wasn’t going to pounce or embarrass her, but I was trying to put some energy in the exchange and drive some spontaneity to the conversation.

Just the night before, Pelosi had been on the front lines of a big budget deal. It was Republican House Speaker John Boehner’s swan song achievement, his last big act before retiring. It passed with votes from Republicans and Democrats alike—a rare event in Washington. Pelosi had rallied support from her side. That’s where I started.

“Budget deal?” I asked.

“Hooray,” was her reply. She smiled proudly.

The presidential campaign was under way and an unlikely candidate was leading the Republican field. I invoked his name.

“Donald Trump?” I asked.

“Performer.” She grimaced.

Abroad, Vladimir Putin was rattling sabers, deploying his military.

“Russia?”

“Careful.” She scowled.

Democrats are perennially on the defensive about big government. Their adversaries like to refer to them as tax-and-spend liberals.

“Taxes?”

Pelosi paused. “Investment.”

Democrats wanted to raise taxes to pay for a range of government programs, so that one word captured their rationale perfectly. In less than a minute, we’d covered several topics—and with an amusing economy of Qs and As. Our political word association game opened the conversation with a few laughs and no speeches, and it established an informal and approachable relationship onstage. It encouraged spontaneity and set Pelosi’s internal clock and her expectations for how I was going to proceed. I think she enjoyed it. I know the audience did because I heard their reaction and laughter and I knew my questions touched on a variety of issues they were following in the news.

Opening with scene-setter questions can help you get people talking, set the pace, and frame the conversation. Figure out what you want to talk about and how, factor in the personalities you have in the room, then map out questions and anticipated responses. You can excite the imagination or you can prompt reflection. It’s your show.

Would you buy a Tesla?

Who’s the most inspiring person you’ve ever met and why?

Set the Stage, Set the Tone

When it comes to hosting, I’ve never met anybody quite like Chris Schroeder. An entrepreneur and an investor, Chris was a digital pioneer, leading WashingtonPost.com in its early days. He invested in a health-related website, built it big, then sold it for a handsome profit. He traveled the world to meet young entrepreneurs who are redefining technology and globalization, and wrote a book.

Chris is a question machine. He recalled that as a young boy, he spent hours with his Italian grandmother, watching her cook, smelling the aromatic tapestry of pastas and meat, onions and garlic, spices and herbs, and asking all he could about the recipes and the family. What was in it? How did she make it? Where did it come from? Where were they from?

Ever since I’ve known him, Chris has been like that—asking incessantly, deeply, about people, ideas, events, and the world around us. He’s an intense and caring magnet for other people as well. They seek his advice because he listens and he asks persistently about opportunities and obstacles, vulnerabilities, and trade-offs.

Exploding with ideas, Chris is driven by his manic curiosity. In his book Startup Rising, he argued that young people in the Middle East embracing technology and innovation will ultimately transform the region in positive and profound ways. For all the turmoil, Chris believes young twenty-first-century innovators are hard at work and will bend history toward knowledge and progress. He is a stubborn optimist.

About twice a month, Chris and his wife, Sandy, host a dinner party. He is a blue-jeans casual, Harvard-educated guy whose interests run from food and sports to technology and foreign policy. Having inherited his grandmother’s love of cooking, he serves up fresh pasta, great wine, homemade everything accompanied by a feast of ideas. His dinner parties are a cross between Top Chef and Meet the Press. On this night, the menu featured fresh pasta amatriciana, lamb stew with mint, and four wines from Italy. He’d sent an email to all the guests twenty-four hours earlier, commenting, “Several of you have asked kindly if you can bring anything, and the answer is no, except an Uber if you will be enjoying some of our wine.”

But think about this, he wrote:

What is something you see in your world that blows you away right now?

Or, what is obvious in your world that to the rest of us may be extremely unobvious?

By the third wine … we may figure out how to save the entire world …

Five couples gathered that Saturday evening at Schroeder’s home, big and warm and welcoming. He and Sandy made gracious introductions, since some of the guests had never met. After some socializing, we moved into the dining room for the main event.

Chris served. Sandy was happy to let him run the show. Their teenage son helped, pouring water and wine, lingering when something caught his ear. After welcoming all of us to his table, Chris slid into his role as host, first offering an observation, followed by a gust of questions. Traveling for his book had given him remarkable access and taken him to places few could visit. He’d just returned from Iran, a place that had dominated headlines and American foreign policy since Islamic revolutionaries stormed the American embassy in Tehran and took hostages in 1979. But now what? Chris told us he had met a new generation of young innovators churning with aspiration, anxious to play, defiant in their ideas, and believing in change. These entrepreneurs were more connected and more empowered than ever, using technology to network with like-minded young people. He saw them collaborating online with other entrepreneurs and innovators around the world. If they had a smartphone, they were not restricted by physical frontiers or cultural expectations. Chris told the story of a young woman who was trying to finance her software startup. She was raising the money to bring her idea to market. And there were thousands like her.

He turned to the table. None of us had been to Iran but he threw out some questions we all could chew on.

How will kids—connected by satellite TV, the internet, and smartphones—change the equation?

How disruptive can they be?

How can any government manage the expectations of this young, globally networked generation?

Could we imagine how things might play out as mullahs are challenged by millennials? What should America and the world do in response?

The table lit up.

The government will build a better firewall, predicted one person.

The kids will find a way around it, said someone else.

Governments cannot keep up with technology or with youth, offered a third.

The ayatollahs still control the country.

The world should lay low and let things play out. Young people have already created a parallel universe where they just ignore what they don’t like. Change from within is inevitable.

Too risky. The hard-liners will never let it happen.

Everyone had a place in the conversation, whether they followed what was going on in Iran or not, because Chris’s questions touched on the universal themes of youth, technology, communication, and the process of change as much as they invoked the particulars and politics of Iran. His questions invited participation at whatever level the guests felt comfortable. He selected a topic he cared about and then framed it in a way that was approachable and real. Most people don’t talk about Iran, but who hadn’t thought about the impact of smartphones and social media in the hands of kids and how they are shaping the future?

The courses came and went and the wine flowed with the topics, as Chris changed direction or deferred to a guest who had an observation on an altogether different slice of life. Spontaneity had a place at the table, too.

“They’re not teaching handwriting in school anymore,” observed one of the young parents, shocked at her own recent discovery. “Cursive will be a lost art.”

What are we losing if no one learns handwriting?

What about the connection between hand, heart, and the creative soul?

Someone had read an article about how handwriting influences reading, writing, and language; soon several of us plunged into a discussion about the virtues of analog relics like pen and paper, hard copy, and real books. Each of us came at the discussion from our own perspective, and each expressed a slightly different view. But everyone seemed to agree in the end that those mindless handwriting exercises actually served a purpose, forcing us to slow down and write between the lines—an enduring gift, perhaps, in an age of digital transience.

It was time for coffee, dessert, and that email question that Chris had sent the night before.

What is not obvious that just blows you away?

We’d all had time to think about it and the answers were all over the map. New technology for the disabled, said one person. Drones, suggested another. But it was Pradeep’s answer that drew everyone in: Air-conditioning.

Air-conditioning?

Yes, said Pradeep. He had recently visited his ancestral village in the state of Tamil Nadu in southern India. He was born and lived there until he was six or so, when he moved with his parents to the United States. His village was a small, remote place of maybe 10,000 people. A few streets passed through the village, crossing near the big temple in town. One of those roads then went down to the river. For centuries the economy revolved around rice, bananas, and mangoes. Lush and deep green, the place had always been defined by its oppressive heat, often exceeding 100 paralyzing degrees.

“I remember in my childhood you would not leave the house during huge chunks of the day,” Pradeep told me later. “Maybe inside you had a fan, but outside it was 100 and you wouldn’t be able to do anything.”

He’d visited periodically as he was growing up and through his college years, but, until his recent visit, he hadn’t been back in fifteen years. He found the changes amazing—an explosion of roads, cars, construction, and smartphones. And that not-so-obvious thing that he now realized had made such a difference was air-conditioning. Air-conditioning meant the place could be tamed, the environment modified. There were now cool spaces where people could work, study, and linger. Yes, Pradeep told us, the air-conditioning that we so take for granted in much of the world had made his ancient village habitable and transformed a way of life that had remained basically constant for thousands of years. Sure, there was still poverty. But this village was morphing from an isolated, subsistence backwater to a modernizing, connected community.

Pradeep’s story enthralled us. He made it personal and real. We learned about him and his ancestral home. He spoke of human progress and connected us to a place no one else had seen. We shared his amazement and discovery. He made us care about his little village and, yes, air-conditioning.

The evening concluded with enthusiastic praise for great food, remarkable conversation, and the new friends we’d made around the table. Chris had been a deft host, dishing up ideas and questions that engaged the room, took us around the world, and got everyone talking. Chris made dinner an event.

You’re On!

Good hosts are always on, always listening, and always interested in their guests and the conversation around them. Their curiosity roadmap reveals their interest in people, places, and ideas. Jimmy Fallon, Ellen DeGeneres, Anderson Cooper, and Terry Gross are powerful personalities themselves, but their first job is to draw out other people and make them interesting, funny, or noteworthy. They ask their guests to contribute new ideas or interesting experiences.

If you’re the host, prepare accordingly. Adopt a strategy that creates the event you want. If you want a fun, free-flowing evening, roll out some questions that tap into the easy currents of daily life. Make them open-ended and friendly questions. Ask about the new restaurant, the local football team, or the new Leonardo DiCaprio movie. If you want be sure everyone participates, try throwing out a question with a challenge: Each person has to answer in just one sentence.

What’s one thing you want everyone to know about you?

If you could transport yourself anywhere in the world right now, go to any country just to eat dinner, where would you go and what would you eat?

Tagine in Morocco? Pho in Vietnam? Ugali in Kenya? Sounds amazing. What does it taste like? How do they make it? Have you actually been there? Now you’ve got everyone’s mouth watering and imaginations going and a roomful of Anthony Bourdains!

By applying a little “conversation leadership” to get people interacting, you can create an environment that is inclusive, interesting, and dynamic. You can host over dinner or at the beach, at the game or in the office. A few well-placed questions will jump-start a conversation. The more you ask, the more you get. You decide what and how much you want to serve up.

The ingredients for this recipe are readily available and require just a little preparation. Start with a few topics that you know interest everyone. Have a few unexpected subjects you’ll mix in as you go. Mix it up with a few lighter, open-ended questions. Listen closely.

Your friend just returned from southern Africa. It was her first time visiting there. She saw the scenery, traveled to Robben Island, and visited Victoria Falls. Your questions, like her travels, reflect different facets of the experience, different levels of awareness.

What did you see?

What surprised you?

How did it affect you?

Daria volunteers at a food bank and feels strongly about the new homeless shelter the city wants to build. Some think it’s necessary but others believe it will attract more homeless people. Ask Daria about her experience and what she thinks about this issue that now divides the community.

What is our obligation to the homeless?

What about the neighbors?

What do the homeless people you know have to say about this?

John loves to camp in the Rockies. He once went for two weeks. Alone.

Why alone?

Any moose join you for dinner?

What do you think about in such solitude?

Ask for different levels of experience and awareness. Decide where and how far you want to go. Start with an open-ended question, then ask about examples and encourage stories. Make room for reflection, humor, and emotion.

Supper with Socrates

If you want to play the ultimate question game and challenge friends and family to look for shadows on the wall of what they believe, invite Socrates to supper. A philosopher and a teacher, his famous line of inquiry is as provocative today as it was 2,400 years ago when he turned his questions on his students. You won’t have to drink hemlock, but be prepared to challenge people to question their knowledge and their assumptions, to the very core of what they believe.

The Socratic method uses questions to probe from all angles. It pokes at a basic premise or value to force critical thinking and get to the root of an idea. It often answers questions with a question in the search for knowledge or understanding. The Socratic method challenges conventional wisdom. It seeks truth and meaning and holds every answer up to the light to ask “How do we know?”

Having supper with Socrates is not for the faint of heart because Socrates was relentless. He questioned his students’ basic assumptions and the very terms of the discussion. He challenged their reasons behind their assumptions. He asked them to consider different viewpoints, then asked where those viewpoints came from and what they were based on. He took nothing for granted.

Socrates might have eagerly joined the conversation at Chris’s dinner party when it turned to the political gridlock that afflicts Washington. One guest groused about the glacial pace of government, noting that America will fall further behind if it continues to move so slowly when the world moves so fast. But then another guest observed that “slow” was baked into our system thanks to our Founding Fathers and their checks and balances. Slow protects us from the impetuous or from over-reaction. Yes, someone else said, but it also prevents us from keeping up with the competition. Then other questions followed: Does anyone really want “fast”? Is there a difference between “fast” and “efficient”? Why can’t we be efficient?

If Socrates had been there, we might still be going. Hang on, he might have said, let’s talk about “slow government.”

What do you mean by slow? According to whom? Based on what?

Can you give an example? Is that good or bad? Why? Is there a better way?

What are the pros and cons? And the consequences? Is that virtuous?

What is virtue, anyway? Better? For whom?

Why did we even ask this question in the first place?

You can see why plenty of people resented the guy, but he sure could keep a conversation going. Despite the dangers, we could invite Socrates to more of our conversations when we’re talking about the vexing issues and tough decisions we confront. We might benefit by having a host who challenges us to open our minds and question our most basic assumptions.

Asking for Laughs

Please don’t think that every time I gather with family or friends for a meal, it’s an interview or interrogation or some deep look into the chasm of the cosmic unknown. Good hosts use questions to have fun, make people laugh, or dive into the ridiculous.

Not long ago, my sister Julie and I were in California, visiting our father and stepmother, Alice. At nearly ninety, Dad still went to his office every day and to the gym twice a week. He looked great and remained eager to enjoy life. Over appetizers, Alice suggested a game my father loved. He’d ask “rating” questions like:

On a scale of one to ten, how important is it to be rich?

What are three qualities you want in a friend?

What are three fun things that matter to you?

Alice told us that she’d asked Dad that last question to figure out what to buy him for Father’s Day. His answer: money, clothes and … sex. For a moment we didn’t quite know what to say. Talking sex with my 90 year-old father was not exactly on my bucket list. Alice, always able to regale a room, leapt on the moment and told us that my father’s answers gave her all the gift inspiration she needed. She bought him an expensive shirt and fine chocolates. The designer label shirt covered her on money and clothes. The Godiva chocolate conjured up sex. Lady Godiva rode naked through the streets, after all. We howled at Alice’s literary license, recognizing that with age comes freedom to say—and buy—whatever you want.

Then she turned to us and said, “Okay, what three things matter to you?” Suddenly we headed in new directions as we listed favorite pastimes and hobbies—long walks in the woods, time on the water, and thoroughly dutiful activities like making a difference and helping others.

Godiva chocolates and sex didn’t come up again, fortunately. But having that conversation around Dad’s table, in his home of forty years, has become one of those postcard moments, when we shared a laugh and creative memories triggered by a silly question.

A Host of Questions

Whether it’s Seinfeld or Socrates joining you for dinner, you can produce an experience your guests will enjoy and remember. They’ll relish the discussion as they savor the food. Your hosting, like the meal, takes some preparation. But it’s manageable if you tackle the recipe one step at a time.

Start with the most important ingredient, the people. The friends, family, colleagues, students, acquaintances in the group may know one another or they may be strangers, so you should find out whether there are common threads and interests. When I interview, I start by asking: Who is my audience? What do they know? What don’t they know? What do they care about? What will they find interesting and funny and why? The more I understand the people in the room, the better I can steer the discussion.

Ask questions, don’t answer them. Good hosts participate in the conversation, of course. But they are principally interested in drawing out the others. Their objective is to direct the conversation not dominate it. Pay attention to who’s talking and who’s not. Direct the questions so everyone gets a chance to talk. But also recognize that some people prefer to listen, so tune in to the signals and listen closely to detect reluctance. Be respectful of the differences.

Mix it up. You can feast on serious topics or small dishes from the lighter side. You can visit a place around the corner or around the world. A good talk-show host alternates topics and moods to keep the conversation moving, varied, and interesting.

Keep watch for the land mines. In my interviews, I go looking for land mines. I like to engage debate head-on. That’s my job as a journalist. But interviewing has also taught me that good hosts go looking for buried treasure, too. That’s how I discover villages in India and my father’s fondest things. But be mindful of topics that at times are best avoided. Politics, religion, and money will inspire some but turn into disasters with others. Know the difference and navigate deliberately.

Go for meaning. Be careful here or you’ll be viewed as the humorless professor rather than the cool questioner. You can take just about any topic and look deeper without making it sound heavy or feel like work. Talking baseball? Sure, the standings matter, but on another level, how can this game possibly survive as the national pastime when it takes three hours to play nine innings and the next generation of fans has attention spans that are suited for text messages and six-second videos?

We never invoked Socrates at that dinner party at Chris Schroeder’s place. We didn’t need to. We were too busy enjoying ourselves, asking and answering entertaining questions, getting to know one another, just having a good time. And examining life along the way.