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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?