Questions to Ask in Business: Fostering Curiosity & Creativity

What question launched Uber? What questions did Toys “R” Us leaders fail to ask?

The most successful companies ask a lot of questions. And, they ask the right questions. That’s the view of Warren Berger. In his book A More Beautiful Question, he explains why every person in every workplace needs to ask the fundamental questions “why,” “why not,” “what if,” and “how.”

Continue reading to learn about these “beautiful questions” to ask in business.

Questions to Ask in Business

Berger says that, just like schools, many companies value knowledge and obedience over curiosity and creativity. However, the most successful companies are those that encourage employees to ask questions and search for innovative answers. Even if you’re not in a leadership position at work (and therefore can’t encourage others to ask questions), you can still ask questions yourself and try to convince your coworkers and bosses that such questions are highly valuable. 

The modern business world changes quickly, and companies need to frequently reinvent themselves to stay relevant. Berger suggests several fundamental questions to ask in business, such as: 

  • Why do some people choose our competitors instead of us?
  • Why not try to reach a new demographic? How could we do that?
  • What if we updated our mission statement to better reflect today’s values?
  • What if a new startup disrupts our market, as Uber did to taxis? 
  • Why not let our employees work from home? 

(Shortform note: In Start With Why, Simon Sinek says that the first question any organization should ask itself is, “Why are we here?”—in other words, “What is this organization’s purpose or mission?”. He gives several reasons for this: First, an inspiring mission will motivate your employees more effectively than paychecks or personal incentives alone. Second, your mission statement will attract customers who agree with it. Finally, a clear mission or purpose will act as a guidepost while you lead your organization through turbulent changes. Before reinventing your company (as Berger says you must frequently do), make sure any changes you make will serve your mission.)

Examples: Uber and Toys “R” Us

The rideshare app Uber came from just such a “what if?” question. Cofounders Garrett Camp and Travis Kalanick got stranded in a snowstorm in Paris, and they wondered: “What if you could use your phone to secure a ride?” However, that concept on its own was worthless—founding the rideshare company that made them billionaires first required them to answer how they were going to do that.

For an example of what happens when businesses don’t ask those questions, consider Toys “R” Us. Toys “R” Us used to be a powerhouse in the children’s toy market. Then, competitors like Walmart and Amazon started crowding the market with huge stores—online and offline—where people could get many of the same goods more cheaply and conveniently. However, Toys “R” Us’s leadership seriously underestimated the threat to their market dominance: Nobody thought to ask, “Why do people like our competitors more than us? What if online purchasing is more than a fad? How might we compete with these new business models? Why not implement them ourselves?”

Because it failed to ask and answer questions like these, Toys “R” Us was forced out of the marketplace by disruptive competitors, and the company declared bankruptcy in 2017.

The Hierarchy of Business Needs

Different authors have different ideas about how to make a business more successful. Gary Hamel and Michele Zanini propose one strategy in their business guide Humanocracy—and, while they don’t explicitly discuss the importance of questioning, their principles may be easier to implement if you also apply Berger’s ideas about fundamental questions.

Humanocracy outlines a hierarchy of needs that all businesses must fulfill if they want to succeed. Much like Maslow’s famous hierarchy of human needs, Hamel and Zanini’s hierarchy begins with fundamental needs (what a business needs to survive) and builds up to what businesses need to thrive.

Their hierarchy has six levels. The bottom three, the fundamental needs, are compliance (following laws, regulations, and best practices), conscientiousness (employees doing their jobs reliably), and proficiency (employees being skilled at their jobs). Until these needs are met, a company can’t function at all. 

However, Hamel and Zanini say that the best companies continue working their way up the hierarchy of business needs. The top three levels of the hierarchy—what a business needs in order to thrive, not just survive—are where Berger’s fundamental questions might come into play. These top three tiers are:

Tier 4: Proactiveness. Instead of waiting to be told what to do, employees are empowered to take action and solve problems on their own. This is where “why?” and “why not?” questions may come into play—employees should be asking, “Why are things the way they are?” and “Why not try something different?”

Tier 5: Ingenuity. In this tier, employees don’t only take action and solve problems—they also do so effectively by being creative. This tier is where “what if?” questions should be encouraged, as these help you make novel and creative connections—for example, “What if the company tweaked its business model in a certain way or added a certain product to its lineup?”

Tier 6: Courage. Employees are willing and able to implement risky ideas and solutions. This is the tier where they should be asking “how?”— “How can they turn their what-if scenarios from the previous tier into reality?” 

Question-Storming Sessions

Berger suggests that to encourage people to ask fundamental questions that support their company, you could try replacing brainstorming sessions with what he calls question-storming sessions. Instead of asking employees to come up with ideas, ask them to come up with questions. There’s no pressure to answer those questions right away; they’re simply possibilities for the group to explore later.

Once a fundamental question has identified a serious issue, your next step should be to ask “what if? questions, even ones that propose strange and outlandish options. Finally, choose one (or more) of those “what if? scenarios and start asking “how? you could make it a reality.

Questions to Ask in Business: Fostering Curiosity & Creativity

Elizabeth Whitworth

Elizabeth has a lifelong love of books. She devours nonfiction, especially in the areas of history, theology, and philosophy. A switch to audiobooks has kindled her enjoyment of well-narrated fiction, particularly Victorian and early 20th-century works. She appreciates idea-driven books—and a classic murder mystery now and then. Elizabeth has a blog and is writing a book about the beginning and the end of suffering.

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