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

CHAPTER 7

IMAGINE THIS

Creativity Questions

CREATIVITY QUESTIONS INVITE US to pull out the paintbrush, throw away the coloring book and think differently. They prompt our imaginations. They ask us to get out of the way, break rules of convention, and exceed the bounds of the possible. They encourage us to rally to greatness or peer into the future, to see a new world. They invite us to daydream.

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What would it be like to ride around like a millionaire?

What a great question. It asks us to envision wealth and comfort replacing the common chore of getting from one place to another. It prods us to imagine how special we’d feel if a deferential driver did the navigating and if convenience replaced stress. No wasted time finding a parking space or hailing a cab. No digging through your pockets for money. (Millionaires don’t carry money, anyway.) You stretch out in the back seat, comfortable and relaxed, managing the empire. Absolute efficiency. Pampered success.

It is the question that animated a couple of techie dreamers in a late-night brainstorming session. Travis Kalanick and Garrett Camp were “jamming on ideas, rapping on what’s next.” Camp came up with a Big Idea: a solution to the horrible taxi service in San Francisco. Camp was stuck on creating a car service that was so efficient people would feel like they were riding like millionaires. In the summer of 2010, the pair launched a tiny company. They called it Uber.

Within four years, Uber reported that riders were taking more than one million trips a day in more than fifty countries. Five years after it started, the company was valued at as much as $50 billion. It inspired the “sharing economy,” as companies like Airbnb, Snapgoods, and Task-Rabbit remade the way people travel, work, buy, and do business around the world. So now we know. If people are given an opportunity to ride around like a millionaire, they’ll do it, millions of times over.

Questions that drive creative thinking are out-there questions. They are big and bold. They ask people to transport themselves to a different time and place and state of mind. They open the door to aspiration and disruption. They challenge the status quo. They reframe issues around visionary, maybe even revolutionary, ideas.

You find inspiration in these fun questions because they invite fresh and original thinking. But you may also feel uneasy when they challenge conventional wisdom and the world you know. Whether you’re trying to invent the next big thing, make a crazy video to sell cars, or write the next inspiring chapter in your life, this line of questioning can help you hatch ambitious new ideas and bring people along for the ride to collaborate and create alongside you. Creativity questions ask you to pretend as they connect you to an imagined reality, where horizons are brighter and where limitations are lifted. They are questions that suggest everything is possible.

That’s what it’s like to ride around like a millionaire.

Creativity questions may not hand you the next $50 billion business, but they will help you put together the best brainstorming session you’ve ever imagined. They will help you reset the dial and think about new ways to get the kids to be on time or eat their broccoli. They will help you bring divergent viewpoints together and think about new ways to address a problem in the community or in the country. Creative questions can become a collaborative quest for answers.

What’s the magic wand idea?

We’ve arrived. What are we doing?

There are no obstacles. Now what?

Creative questioning asks people to close their eyes and imagine. It welcomes crazy ideas, shrugs off the obvious, and seeks alternatives. Creative questioning asks fellow travelers to:

Set sights unreasonably high. Ask more of yourself and others without being limited by the laws of gravity. There will be plenty of time to come back to earth later. If you don’t aim high, you will never go into orbit.

Try a little time travel. Creative thinking is all about the future, so go there. Put your questions in the future tense and ask people to transport themselves there with you.

Invoke imagined reality. Role-play. You’re living in that new world, workplace, or community. What’s it like? Look up, down, 360 degrees around. What do you see? What do you think? What’s next?

Embrace disruption. Questions that drive creativity involve disruptive thinking that can be unsettling, uncomfortable, and sometimes downright subversive. That’s how we change the world.

Beyond the Possible

Creativity questions reach for the stars. Which is how we got to the moon.

When Soviet cosmonaut Yuri Gagarin became the first human being to go into space on April 12, 1961, a wave of patriotic pride washed across the Soviet Union—and panic engulfed America. The Soviets were winning the Cold War in space.

President John F. Kennedy consulted the experts and set his sights on the moon. In May, he asked Congress to fund the initiative, noting that the scale of the project was so huge that “it will not be one man going to the moon … it will be an entire nation. For all of us must work to put him there.” Then he set about selling the idea, asking Americans to be bold, think big to do something that had never been done. Kennedy came into office “asking” the nation to think, not about what the country could do for them but what they could do for their country. Now he wanted them to think outside their planetary constraints. When he spoke at Rice University in September 1962, observing that America had always thought big, he posed a set of questions.

But why, some say, the moon?

Why choose this as our goal?

Why climb the highest mountain?

Why, thirty-five years ago, fly the Atlantic?

We do these things, the young president famously said, not because they are easy, but because they are hard.

The brilliance of Kennedy’s questions—which were a hallmark not just of the moon shot but so much of his Camelot presidency—was in their ability to appeal to the country’s imagination, greatness, and sense of destiny. They asked Americans to rise to a challenge, to look to the future and to answer a higher calling.

The response was hardly unanimous. The Apollo mission was brave and brilliant, but according to Gallup polls conducted before the landing, it never enjoyed majority public support until the day the lunar module actually touched down on the surface of the moon. But when the time came, one out of every seven people on the planet watched the moon landing on TV. I was a kid at summer camp and listened on a battery-operated transistor radio as Neil Armstrong set foot on lunar soil and took his one step for humanity and read from a plaque on the leg of the Eagle Lander, “Here men from planet Earth first set foot on the moon … we came in peace for all mankind.” On that magical day, July 20, 1969, we rose to an extraordinary challenge and answered Kennedy’s questions in a way that captivated the planet.

Travel in Time

When we ask people to time travel—to fast-forward themselves to another place, another time—we issue a ticket to creative thinking. There are few moments in human history that rival the mission to the moon, but we envision the future every day. It’s how we set our sights and articulate ambitious goals.

When I started my term as a trustee for my alma mater, Middlebury College, the president was in the early stages of crafting a ten-year strategic plan. At our fall retreat, a facilitator started with a question that invited us to think creatively about the college’s future by going there.

“It is ten years from now,” he said, “and the latest college rankings have just come out. This school is at the top of the list. What are we doing?”

He put the future in the present tense. His question was a time machine. Once we stepped inside, the obstacles that often interfere with big ideas—practical considerations like cost, resources, staffing, and economics—fell away. We traveled past them and arrived at our destination, where we were the best. In our very own virtual reality, we looked around and listed the qualities that earned us the top spot. There was a new science center, a new library, more students who brought more diversity, more faculty, and more funding. The future was clear!

Everyone played. Then we worked backward to determine how to make it happen, from program design to funding. Today, the college has a beautiful science center and library. There are more students and more faculty. The school is in the top ranks of liberal arts colleges. We did it. Imagined reality became actual reality.

Since that retreat, I have used this technique many times, asking people to time travel to visit the future and see it for themselves. Imagine. It’s five years in the future. Your business has moved from number twelve in the marketplace to number three.

What are you doing?

Who are your customers?

What are you known for?

What are you proudest of?

Ask about the future in the present tense. Once you have articulated it, work to achieve it. There are no guarantees, but you can now ask what it will take to hit your benchmarks, who needs to do what, against what odds, and at what cost. You build a brick at a time. But it’s a lot easier when you’ve seen the place and know where you want to go and why.

Cutting Strings

How can questions convey authorship and drive genuine collaboration? How can they encourage people to take ownership of an idea or a concept and think differently, be original, and strive for the truly creative, maybe even the off-the-wall?

I wanted to explore those questions from a different perspective, far from the high-stakes stuff of space travel, politics, and technology. So I decided to go to where imagination exists for its own sake: Hollywood. Now, when you think of Hollywood, deep thought may not be the first thing that comes to mind. However, it is a place where creativity is an industry, where collaboration is a high-voltage necessity and success is measured in numbers—ratings and revenue.

I called my friend Tom Hoberman—a super-agent lawyer in LA who knew just about everyone—and asked him to connect me with the most creative, most inquisitive person he could think of. In a nanosecond, he recommended Ed Bernero, an insanely creative guy whose unlikely trajectory drove a supersonic career.

Ed is a big man with a big personality. His voice booms and stories spill out of him. He is a show runner, director, writer, and producer. He’s been involved with hit shows like Third Watch, Criminal Minds, and Crossing Lines. He mines the talent of everyone around him by shoving them out of their comfort zones and into their stories and their characters. He does it with questions that place writers, actors, and others into the imagined reality of story.

Ed isn’t a central-casting kind of Hollywood player. He grew up rough in Chicago, seeing his father beat his mother. As a young kid he called the cops more than once. He saw the police as his protectors. After a stint in the military and jobs working for security firms, he became a Chicago cop himself. He lasted nearly ten years—until he quit to save his soul.

Being the good storyteller he is, Bernero describes the scene when he realized he was in trouble, the protagonist confronting his discovered vulnerability. Ed and his partner were two good cops on patrol in a rough neighborhood. They stopped at the liquor store where they checked in every day and where a big guy I’ll call Lee kept them up to speed on what was happening on the streets. Lee sold them cigarettes for a quarter a pack. Cheap cigarettes, street-smart cops, and everyone was happy.

One night, Ed stopped by as usual, only to find a stranger behind the counter.

“Where’s Lee?” he asked.

“They killed him this morning,” the woman said. “Shot in the face.” Ed was stunned. He went back to his patrol car and sat there. His first thought: “Where am I going to get cigarettes for 25 cents a pack?” Then he stopped. Lee was dead, and Ed found himself thinking about cheap cigarettes? He shook his head and looked down as he told me the story. It was the moment he knew he had to get out. “That job is a complete erosion of your humanity.”

Ed didn’t get out for another five years. But he began writing screenplays in his basement. “Not as a job,” he told me, “but as therapy.”

One day, a friend was picking up an NBC executive from the airport to speak at Northwestern University. Ed’s wife had slipped her one of Ed’s scripts and asked her to pass it on to the visiting exec. Within days, Ed got a call. Good stuff, he was told, sit tight. More agents and producers called asking for meetings—invoking some of the biggest names in Hollywood: Steven Bochco, John Wells, David Milch.

Three weeks shy of his tenth anniversary with the Chicago police department Ed Bernero pulled his money out of his home, cashed in his pension, and hauled his family across the country. Within a month, he had his first freelance gig—with super-producer Steven Bochco on the CBS police drama Brooklyn South. Following that, he worked with John Wells on the NBC hit show Third Watch. Ed ended up doing more than 130 episodes of New York cop dramas, many of them drawn from his own experience.

But Ed found Hollywood a strange place—riddled with back-lot intrigue, hypersensitive egos, and no shortage of pandering and posturing. Directors, producers, show runners, and studio execs maneuver for recognition and influence. Writers think every word is a gem. Actors take their craft, and themselves, very seriously. Just about everyone is insecure or desperate to get the big break and will say anything to ingratiate them with whoever is calling the shots. Ed once wrote a deliberately terrible script and took it to a crew meeting to see if anyone would call him on it. They didn’t. He realized that if he was going to get genuinely creative work out of his team and not just his own ideas thrown back at him, he needed to engage them differently. He couldn’t bark orders—he had to ask.

You can’t treat people like puppets on a string, Ed told me.

The creativity Ed wants to inspire requires collaboration. “I want everyone to be involved in the show,” he said. It starts in the writers’ room, where ideas collide in mid-thought and mid-air. The room is dominated by a big table that is bounded by whiteboards and littered with chips and pretzels and energy food. This is where Ed’s writers “break the story.” They jot down an idea, kick around plot points, story elements, twists and turns, and imagine how the whole thing unfolds.

Ed wants his writers to construct original, bold, surprising stories—to “color outside the lines.” But he knows that if he tells writers what he’s thinking about a scene or a character, they will be tempted to run with it, play it safe, and give him what they think he wants. So he uses questions to challenge the room.

What if the hero shows up late?

What if the bad guy missed his mark?

The questions are designed to get the writers and the rest of the crew peering around the corner, inventing surprising twists and turns in the story. Ed uses this technique to foster an atmosphere that’s edgy, highly charged, and fun. He wants brainstorming and energy. He also wants creative tension. Ed can be a pain in the ass, and he knows it. He will send scripts back to the team with corrections and complaints. He will say something’s terrible. He usually eats lunch alone in his office. It’s not because he’s shy. He wants to give his team their space. “I want them to bitch about me,” he told me. “I want them to care enough to be upset. I tell them all, at some point during the season you’re going to hate me. That’s okay. It’s like a family. You can storm out. You can be emotional.”

Ed barks questions, not orders, to challenge his writers.

How can you improve the character?

What happens next?

But he also uses questions to make people feel involved and invested. “Otherwise they will just sort of quietly wait for you to say something, and go and do it. It’s the same with the crew as it is in a writing room. I can change the whole direction of the story just by saying something.” Ed believes he brings out the most creative thinking from people when he asks.

He recalls shooting a scene when an actor playing a cop couldn’t nail the timing of a critical move. Squaring off in the street against a woman who is the prime suspect in a criminal investigation, the cop gets his first opportunity to question her. She is crouched and defensive. The cop studies her through his sunglasses, sending signals of authority and accusation. At the right moment, the cop pulls away his sunglasses to make eye contact. After several tries, Ed sees it isn’t working.

“Take five!” Ed calls out, approaching his cop-actor to discuss the scene. Ed does not tell him, “On the third line take your sunglasses off….” Instead he asks, “When do you think this character would want to show his eyes? That’s the moment the suspect sees into you.” Ed wants his actor to think about his eyes, not the glasses. “So when do you want that to happen?”

By turning a direction into a question, Ed handed the responsibility for the answer to his actor, asking him to picture the scene and solve the problem. It wasn’t just about his lines, it was about the chemistry between two characters that, in turn, shaped the story. The actor had to feel it intuitively. The next take, Ed recalled, was perfect.

“Actors are extremely emotional people and extremely sensitive,” Ed explained. “You can’t just go in and tell them. You have to find a way to ask and find out what they’re thinking and value.” Once you do that they help answer the question. Now they can close their eyes and imagine.

Ed could be talking about anyone in any place. If you’re trying to devise a new way of approaching a problem, if you’re hoping to get the creative juices flowing, your question can be an invitation.

How would you do this differently?

What’s your new idea?

These questions are invitations to contribute and create. They send a signal of respect. They offer a challenge that says, “you are a valued part of the expedition. Where to?”

Imagined Reality

Creativity questions have an almost magical capacity to transport people to a different time, place, or perspective. They help us get to that imagined reality. Like Ed Bernero, we can use these questions to craft a story that’s original and different.

A publisher friend of mine, Jay, convened an off-site retreat with his top editors. He began with an exercise. Crunch time had arrived and each magazine had to cut its budget by 50 percent. He asked:

What do you cut?

What do you do?

Were do you start?

The teams went to work, prioritizing and calculating, cutting staff and expenses and page counts, looking for savings in paper quality and marketing. They looked at circulation and administrative costs. Though this was just an exercise, everyone played along and took it seriously.

Then came the twist. In a surprise move, Jay gave his editors their money back. Every penny. But he told them to use the budget they’d cut just a few minutes earlier as their new baseline. They could invest the money they had “saved” in any way they wanted.

What will you build?

How will you invest?

Their answers helped transform the company’s five newsstand magazines and led to more National Magazine Awards than any of their rivals. The net profit for the company doubled in two years.

Asking people to play a role and answer a series of questions or a challenge catalyzes creative thought and innovation. The consulting firm McKinsey & Company examined the best ways that businesses could use insights from neuroscience to unleash creativity and innovative ideas in their employees. McKinsey cited the work of neuroscientist Gregory Berns from Emory University, who found that creativity requires “bombarding” our brains with things that are new, unfamiliar, and different.

The McKinsey authors stated, “only by forcing our brains to recategorize information and move beyond our habitual thinking patterns can we begin to imagine truly novel alternatives.” They cited a Harvard Business Review article in which professors Clayton Christensen, Jeffrey Dyer, and Hal Gregersen list five “discovery” skills for innovators: associating, questioning, observing, experimenting, and networking. They found that making connections across “seemingly unrelated questions, problems, or ideas” was the most effective path to innovation and that analogies—comparing one company to another, just as Kennedy compared Apollo to Lindberg and as the Uber boys created a comparison between a taxi and a millionaire’s limousine—led the teams to “make considerable creative progress.”

They provided some sample questions that businesses could use in a brainstorming session, asking what the best in the business would do in their shoes, drawing comparisons that most closely applied to their own challenges. After all, creativity questions should be aspirational.

How would Google manage our data?

How might Disney engage with our consumers?

How could Southwest Airlines cut our costs?

How would Zara redesign our supply chain?

Pushing people out of their “habitual thinking patterns” is an exercise anyone can do. Imagine that your daughter just won a full-freight scholarship to any school in the world. Ask her:

Where would she go?

What would she study?

What opportunities would she have?

Or imagine you were named CEO of your company.

What would be the first things you would do to improve morale and performance?

Role-playing puts people, like Ed’s actors, in an imaginary place and asks them to play their part. The exercise works because, often without realizing it, players combine imagination with intellect and get into the game. They think in a hypothetical space and craft their responses to keep up with a storyline they cannot control or predict.

After the 9/11 terror attacks, I ran an exercise with about two dozen governors from across the country. They sat around a big horseshoe-shaped table. They knew the stakes and they were up for the game. My job was to steer them through the scenario to test response and readiness. I opened with a video “news report” of an attack on a shopping mall. Early reports indicated many casualties. Emergency responders were on the scene, but it was a confusing, chaotic situation. Cable news and local TV channels had scrambled trucks, cameras, and crews. The “experts” speculated. Several of them predicted more attacks. I put the governors in the middle of this situation and asked them to envision the scene and their response.

What was the first call they made?

Who needed to be in the room?

What would they tell the public?

A few minutes into the game, I turned to a governor from a midwestern state. I asked him what he was doing amid the heightened alert. Watching closely, he said, but not much more because his state didn’t really have strategic targets and had never considered itself seriously at risk. I was stunned. Did he really think anyone was immune from this scourge?

So I added a few more details. I said I was an editor at the Wall Street Journal and I wanted to see how the terror alert was playing in places that were off the beaten track and previously had not faced a serious threat. The assignment: Are they prepared or are they complacent? What are they doing? I’d dispatched one of my best, toughest reporters to his state to do the story, I told the governor. She was waiting outside his office now.

What will you say?

What is your headline?

The governor’s expression changed. It was as if someone had told him his fly was down as he stepped away from the podium after a big speech. I could see the wheels turning. Reporters? Publicity? Headlines? Well, he said, he would explain how he had met with his emergency management and law enforcement teams. He was coordinating with the Department of Homeland Security. He was monitoring the situation, urging people to be calm but vigilant. Suddenly we had one very in-charge governor. By asking him to imagine himself in a different, fictional place, I prompted him to think hypothetically—creatively.

Afterward, one of the governor’s top emergency management aides took me aside and thanked me, quietly observing that the role-playing questions were just what the governor needed to understand what was at stake, and that such a scenario could actually happen. He needed to imagine reality to appreciate it.

Ask for Subversion

Creative, disruptive thinkers are unafraid to ask questions that push the bounds of the present and the possible. They see the world differently and challenge it profoundly. They ask more of themselves and everyone else. Sometimes they are celebrated, sometimes they are vilified. Which is what drew me to the former mayor of San Francisco. Gavin Newsom, defined by his contradictions and known for his willingness to experiment, posed questions that put him on the front lines of astonishing and controversial social change.

At just thirty-four years old, Newsom was the youngest mayor elected in San Francisco in more than a century. He brought boundless energy, a conspicuous determination to innovate, and one of the most interesting pedigrees of anyone who’d ever occupied the job. He was raised by a single mother who took in foster kids and worked three jobs to make ends meet. Hampered by dyslexia, a disability that required special classes and extra effort, and left him “unbelievably timid and insecure,” Newsom developed a different way of looking at the world and a deeper appreciation for the underdog and the outcast. As a kid, Newsom had a rough ride. Students laughed at him when he tried to read out loud. Teachers wrote him up for a lack of engagement and focus. He plowed his way through school, but ended up attending half a dozen different schools in eight years.

Though the family had little, they were lucky that a fortuitous friendship had endured. Newsom’s father, Bill, went to school with super-rich Gordon Getty, and they had remained close. Young Gavin became friends with Getty’s son. He hung out with the family, flew on their private planes, and joined them on African safaris. The Gettys liked Newsom’s originality, his sense of adventure and willingness to take risks. They saw potential. Later, they invested in his businesses, which propelled Newsom to wealth, fame, influence—and City Hall.

Newsom remains a study in contrasts. He advocates for the little guy but he cavorts with high rollers. He loves politics but hates what it has become, too often driven by money, self-interest, and ideology. He knows he must build coalitions, but he insists he’s still a risk taker. He takes special pride in a plaque on his desk. It is a question. Everyone who comes into his office sees it.

What would you do if you knew you could not fail?

“I challenge my staff and those around me to ask it,” he told me. And he challenges himself with it. His first test, and the controversy that was to define him as a politician, came less than two weeks after he was elected mayor, when he attended President George W. Bush’s 2004 State of the Union address.

The galvanizing issue was one that reverberated back in San Francisco—same-sex marriage. The president previously had expressed his fierce opposition to it. He was a staunch supporter of the Defense of Marriage Act, which defined marriage as a strictly heterosexual institution. But in this speech, Bush went further. He said he supported a constitutional amendment enshrining marriage as a union between a man and a woman. The speech disturbed Newsom, but a comment afterward enraged him. As he lined up to leave the chamber, Newsom overheard a woman talking about how proud she was of the president for standing up to “the homosexuals.” Newsom left Capitol Hill fuming, thinking it was a good thing that few recognized the new, young mayor from gay-friendly San Francisco.

The first person Newsom called was his chief of staff, Steve Kawa—the first openly gay man to serve in that position. Newsom told him they had to “do something about this.” When he got home, Newsom convened his team. He posed the questions he’d been asking himself over and over again since the president’s speech.

What is this really about?

What values are at stake?

What was the point of becoming mayor?

What did we come here to do?

By now, Newsom viewed the issue as a fundamental matter of fairness and equity. He was leaning in favor of unilaterally instructing City Hall to issue marriage licenses to same-sex couples. Initially even his gay chief-of-staff was opposed. “He fought me,” Newsom explained. “He was emotional about it.” Kawa saw huge political risks; he knew that it would put everyone in the spotlight and stir up more controversy, even in San Francisco.

“He said it was hard enough to come out to his family,” Newsom recalled. But the mayor decided gay people had a right to get married if they wished.

When City Hall opened for business on February 12, 2004—just three weeks after Bush’s State of the Union speech—gay couples could apply for marriage licenses for the first time ever. Thousands showed up. Sure enough, Newsom’s act of defiance drew the wrath of Republicans and Democrats alike.

“My party leadership was furious and read me the riot act,” he said. California senator Dianne Feinstein all but accused the young mayor of sowing the seeds for the Democrats’ defeat in the fall’s presidential election. Newsom wasn’t sure he would survive the storm, but he held his ground. Defending himself on CNN, he said that denying the right to marry “is wrong and inconsistent with the values this country holds dear.” He added, “And if that means my political career ends, so be it.”

His career did not end. On the contrary, he won reelection with 72 percent of the vote in 2007. He is now lieutenant governor of California with aspirations for higher office. In the decade since San Francisco City Hall issued its first marriage license to same-sex couples, judges, legislatures, and, in 2015, the Supreme Court voted to legalize same-sex marriage. Whatever you may think of Newsom, his role as a change agent on this issue can be traced to those questions he asked himself after hearing a speech. They forced him to step back from the noise and the risks and look at the issue differently. They led him to think differently and defiantly about a once-unimaginable future. Simple questions.

What is this about?

What are our values?

What was I elected to do?

Creative questions ask you to close your eyes and imagine. They are aspirational, often inspiring, and sometimes subversive. They embrace risk and challenge our brains to look through a different lens. While they can be adventurous, even exhilarating, they can also be lonely and controversial.

You can ask these questions of your inventive colleagues or your reluctant stakeholders. You can pose them as a game or as a challenge. You can frame them around the future as you ask for new ways of thinking and doing that will get you there. Creativity questions are daring, liberating queries that invite you to stick your head in the clouds, ask more of everyone, and imagine just how far you can go.

What would you do if you knew you could not fail?