A More Beautiful Question (14 page)

The easy answer is sixteen. But the more observant people in the group are apt to notice—especially after Srinivas allows them to have a second, longer look—that you can find additional squares by configuring them differently. In addition to the sixteen single squares, there are nine two-by-two squares, four three-by-three squares, and one large four-by-four square, which brings the total to thirty squares.

“The squares were always there, but you didn’t find them until you looked for them,” Govindarajan and Srinivas wrote on the
Harvard Business Review
blog, after they published the puzzle there. (They got hundreds of responses from readers, whose answers to “How many squares?” ranged from sixteen to thirty up to sixty—if you count the thirty squares with black edges as well as the thirty with white edges—and all the way to infinity.)

Srinivas told me he uses the exercise to illustrate that we often fail to see all the possibilities available to us because we simply haven’t spent enough time looking. He said the exercise particularly resonates with people who are in a difficult situation: “Sometimes people feel like they have nowhere to go and they’ve run out of options, and my point is, ‘There is always another square, another possibility, if you just keep looking for it.’”

Why can’t computers do more than compute?
²¹

In the 1950s it wasn’t clear how computers could be used outside of mathematics. Conway Berners-Lee, a British mathematician who worked on the early commercial electronic computers, was fascinated by the question,
Could computers be used to link information rather than simply compute numbers?
The question was later refined by his son, software engineer Tim Berners-Lee. Overwhelmed by massive amounts of research data, Berners-Lee wondered if there were a way to combine the nascent Internet with linked hypertext documents to better find and share information. In 1989, he proposed the global hypertext project to be known as the World Wide Web. His prototype included the now familiar architecture of web browsers, HTML, HTTP, and URLs.

Great questioners “keep looking”—at a situation or a problem, at the ways people around them behave, at their own behaviors. They study the small details; and they look for not only what’s there but what’s
missing
. They step back, view things sideways, squint if necessary. In Sutton’s writings on vuja de and how to see the familiar, he advises “shifting our focus from objects or
²⁰
patterns in the foreground to those in the background.”

Such close observation demands patience and persistence. After seeing the first sixteen squares, we’re inclined to move on and look elsewhere; but the thirtieth square, the one you notice later, can turn out to be a window of opportunity that others haven’t yet seen. Einstein talked about looking for the needle in the haystack and finding it—at which point most people stop looking. The secret, he said, is to keep looking, in search of an even better needle.

Why should you be stuck without a bed if I’ve got an extra air mattress?

In the fall of 2007, Joe Gebbia and Brian Chesky had one question uppermost in their minds, and it wasn’t a beautiful one. “How were we going to pay
²²
the rent?
That
was the main issue at the time,” Gebbia recalls. He and his roommate, Chesky, had no jobs, and not much money. But they did have a decent San Francisco apartment with a place to sleep and a roof over their heads. Which was more than could be said for many of the people coming to town for a local business conference—the city’s hotels were all booked, and conference-goers were desperate for a place to stay.

This situation (which Gebbia and Chesky had experienced firsthand as visitors to prior conferences) didn’t make sense to them:
Why can’t we find a place for these people to crash for a night or two?
Which then led to
Why not our place?

Gebbia and Chesky got hold of three inflatable air mattresses. They could simply have run a cheap classified ad, rented out their airbeds for a modest fee during the conference, and picked up enough money to cover a small portion of that month’s rent. But almost immediately, they started to think bigger about this idea and asked all kinds of What If questions, such as
What if we provide more than just a mattress to sleep on?
They didn’t have much to offer, but they threw in a modest breakfast (how modest? Pop-Tarts!) and sightseeing tips. And rather than just put a listing on Craigslist, Gebbia and Chesky (who both had a design background) thought,
What if we create our own website?

They did all of this, rented out the three mattresses to three individuals who didn’t know each other, and everyone enjoyed the experience. Gebbia says, they now started to think,
Why not make a business out of this?
What if we could create this same experience in every major city?

Here is where the two dreamers ran headfirst into conventional wisdom. Initially, no one, outside of Chesky, Gebbia, and a third partner they brought on, thought this was an idea that made business sense or was worth supporting. Paul Graham, a renowned angel investor in Silicon Valley who runs the start-up incubator firm Y Combinator, believed quite simply, “No one would want to stay in
²³
someone else’s bed.”

The idea that would eventually become Airbnb was challenging a basic assumption: that you needed established, reputable hotels to provide accommodation for out-of-town visitors. Those paying close attention might have noticed that just a few years prior to this, lots of people held similar assumptions about cars—you could buy them, you could rent them, but there was no practical way to
share
them. Then an entrepreneur named Robin Chase asked,
Why not?
—and subsequently introduced Zipcar.

Gebbia told me that part of the reason he and Chesky believed this was a problem worth solving—the reason, he suspects, that they saw what others missed—was that they had been on both sides of the problem. “We knew what it was like to come to town needing a place to stay, and we knew what it was like to have extra space that we needed to rent,” Gebbia said. “So we connected those two dots. In retrospect it makes complete sense—but at the time, no one else had connected those dots.”

Gebbia and Chesky had a kind of “rebel” attitude that goes with successful questioning. It’s one thing to see a problem and to question why the problem exists—and maybe even wonder whether there might be a better alternative. It’s another to keep asking those questions even after experts have told you, in effect, “You can’t change this situation; there are good reasons why things are the way they are.”

Gebbia and Chesky had to overcome that initial resistance by continuing to push forward on their original question (about whether they could expand that first hosting experience into a business), and they were propelled by new questions at each step of the way. They wondered,
What if we take this idea on the road and test it in another city?
With the 2008 Democratic presidential convention in Denver, they found the perfect place to launch—lots of people coming into town, not enough hotels.
But
how would those visitors, and the people with space to rent, learn about Airbnb?
Gebbia and Chesky couldn’t afford ads; so they had to make news. The founders knew that the news channels would be doing stories about how crowded and overbooked Denver was. They pitched Airbnb as a “solution story” to news producers and ended up on CNN. The bookings came in and the Denver launch was a success.

But Gebbia says they kept questioning, kept iterating and refining the model for another year before they felt they had it right. They used the site themselves, stayed in rentals, and asked,
What’s working here and what’s not?
When they noticed, for example, that exchanging money with apartment hosts was awkward—“It just felt like the whole experience was relaxed and fun, until it came time to pay,” Gebbia recalls—this spurred them to ask,
What if you could pay online?
When they noticed that many of the visitors to their site were asking about foreign cities, this led to a big question:
Why are we limiting this to the U.S.? What if we go global?
Within less than two years, they were in more than a hundred countries, doing a million bookings, and flush with more than one hundred million investment dollars. They had even won over early skeptics such as Y Combinator’s Graham, who became one of their seed investors.

These days, Gebbia and Chesky are asking a whole new set of questions about whether it’s feasible to create a “sharing economy.” At the core of this idea is the fundamental question
Why should we, as a society, continue to buy things that we really don’t need to own?
(Consider, for example, that the average power
²⁴
drill in the United States is used a total of thirteen minutes in its lifetime.) As Gebbia notes, we’ve spent decades accumulating “stuff” in the modern consumer age.
“
What if we spent the next hundred years sharing more of that stuff? What if access trumped ownership?
”

Whether or not Airbnb, joined by others, will be able to successfully lead that ambitious “sharing economy” movement is an open question, and one that—even more than the earlier questions about whether people would be willing to share homes and beds—aggressively challenges assumptions about how our economy works, the extent to which people are willing to change ingrained behavior, and whether sharing even makes sense as a viable business model.

Why can’t India have 911 emergency service?
²⁶

This was the question Shaffi Mather tackled, following a health emergency involving his mother. He started with one ambulance and a simple number (1298) that people could dial in a crisis. But the toughest question was,
How much should we charge?
Mather wanted the service to be available to everyone, so he tried a pay-what-you-can honor system—but everyone claimed to be poor. So he inquired,
How can we get those with money to pay more?
The answer: The better the hospital you requested, the more you were charged for the ride. With backing from the Acumen Fund, Mather’s service became Asia’s largest ambulance company, transporting nearly 2 million people. Mather kept questioning along the way, with occasional misfires: Once, to try to cut costs, he asked,
What if the ambulance doctors also carried the cots?
The lesson learned: people assume that any doctor who has to carry cots must not be a very good doctor.

Clearly, though, the success Gebbia and Chesky have already achieved is rooted in their willing-ness to challenge assumptions and to believe that everything is subject to change—regardless of what conventional wisdom holds. I think of this brand of questioning as a subcategory of Why questions that could be considered “challenger questions.” They have a certain attitude about them: restless, rebellious, skeptical of convention and authority. As in:

Why should we settle for what currently exists?

And
why should I believe you when you tell me something can’t be done?

Asking challenger questions is inherently uncomfortable—“it creates dissonance,” notes Paul Bottino,
²⁵
who directs Harvard University’s student-innovator program. The program draws some of the brightest, most creative college students—yet even those students arrive with a tendency to accept much of what they’re told without question, Bottino says. One of his chief tasks is to teach them “to understand that the incumbency has an interest in maintaining the status quo. To question well, you must have the ability to say, ‘It doesn’t have to be that way.’”

That goes against what many are taught in school: that each question has one right answer and you’d better accept it (and memorize it). When Deborah Meier established her Central Park East School designed to encourage questioning, the first “habit of mind” she taught her students was to ask,
How do we know what’s true?
Meier wanted them to question everything they were taught and all they were told. George Carlin had a lifelong mistrust of authority, Kelly Carlin noted, and his advice to parents was “Don’t just teach your children to read. Teach them to question what they read. Teach them to question everything.”

After years of being conditioned to think that “answers” coming from “experts” should be accepted, the only way to get more comfortable questioning the expert assumptions of others is to do it repeatedly and over time, Bottino says. Among the things one must get used to, in asking challenger questions, is that you’re likely to be asked the classic antichallenger question:
What makes you think
you
know more than the experts?
(The answer is that you don’t know more, you know less—which sometimes is a good thing.)

Another common counterquestion that challengers can expect to be hit with is some version of
Okay, genius, how would
you
do it better?
An interesting assumption is built into this question: that if someone is going to challenge the existing ways, then he/she had better have an alternative ready. But it’s important to ask
Why and What If questions even if we don’t yet know the How
.
Getting to a better alternative may be a long process, but it has to start somewhere—and that starting point often involves questioning the status quo.