PDF Summary:A More Beautiful Question, by Warren Berger

Asking questions is a crucial part of critical thinking: Questions are how you increase your knowledge, and searching for answers to your questions is the basis of creativity. However, as you grew up, you likely fell out of the habit of asking questions. In A More Beautiful Question, author and journalist Warren Berger highlights three fundamental questions—“why?”, “what if?,” and “how?”—which you almost certainly asked all the time as a child. He argues that by asking the right questions, you can discover how to succeed in both business and life.

In this guide, we’ll explore how to use these fundamental questions effectively as an adult. In our commentary, we’ll discuss research supporting Berger’s suggestions, as well as some practical tools to help you develop a curious, questioning mindset. We’ll also compare and contrast Berger’s ideas with those in other influential self-help books such as Atomic Habits and business guides like Purple Cow.

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However, to turn a creative idea into reality, you need to answer the third and final fundamental question: “how?” Berger says this is the most difficult step—fully answering “how?” often requires patience and commitment to your idea because the answers tend to be much more complicated than they seem at first.

Continuing the example of Uber, the co-founders had come up with a new concept: using a 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.

Furthermore, that answer (a relatively simple smartphone app) led to numerous other questions, as Berger says is likely to happen: For instance, how would they compensate the drivers? How could they make riding with strangers as safe as possible? How would they outcompete local taxi services? Fully answering these “how?” questions led Camp and Kalanick to found one of the world’s most successful startup companies.

A Follow-Up Question: How Can You Best Leave Your Options Open?

When Berger discusses answering a “how?” question, he’s arguably talking about making a plan: coming up with a series of actions and predicting their outcomes, with the ultimate goal of turning your “what if?” scenario into reality. That may be why answering “how?”is so much more difficult than it appears—instead of just answering one question, you’re undertaking a multi-step process that involves choosing a goal, determining how to reach that goal, and then doing it.

However, thinking too hard about your “how?” can be counterproductive. In Antifragile, risk analyst Nassim Nicholas Taleb warns against relying too heavily on predictions and plans. He says the world is so complex that predicting events is nearly impossible: For instance, consider how unreliable long-term weather reports tend to be. Further, an incorrect prediction can cause your entire plan to fall apart. Therefore, another important question to ask is, “How can I protect this plan from unexpected events?”

According to Taleb, the answer is to rely on options instead of predictions. Options protect you from the world’s uncertainty because, no matter what situation you’re in, you can choose the best option available at that moment. On the other hand, if you’ve created a strict step-by-step plan based on predictions, you become lost as soon as one of those steps doesn’t work the way you expected it to. For example, if you hire more employees based on a prediction of how quickly your company will grow but actual growth doesn’t match your projections, you stand to lose a lot of money.

So, if you’re trying to start a business (such as Uber), Taleb would say you shouldn’t rent office space until you can’t proceed without it—it might turn out you don’t need a physical office at all. Similarly, don’t hire any employees until it becomes clear that the business has become too big to handle on your own. The money that goes to pay an employee’s salary might have been better spent on, say, speaking with a business consultant or covering unexpected overhead costs.

Ask Questions in Business and in Life

Now that we’ve reviewed the fundamental questions, this section will explain how you can use those questions to find success in business and life.

Ask Questions to Succeed 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. That’s why employees and leadership alike should always be asking fundamental questions, 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 guide 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.)

You’ve already seen what happens when companies ask fundamental questions with the previous example of Uber. 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?”

Tip: Replace Brainstorming With Questioning

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.

Berger believes this practice is more effective at generating ideas than traditional brainstorming sessions because, if the only expectation is to ask questions, there’s no pressure to also come up with solutions on the spot. This reduced pressure helps people’s thoughts to flow freely, and it makes them less likely to censor their ideas. By contrast, in brainstorming sessions, people naturally feel like they have to come up with “good” answers. Therefore, they might hold back potentially transformative ideas that they feel aren’t good enough.

(Shortform note: Many experts agree with Berger that group brainstorming sessions are ineffective, and some research supports this—one study of over 800 teams found that the group produced fewer and lower-quality ideas than the same number of people would have produced while working alone. One possible reason for this is the pressure for solutions that Berger mentions. Another explanation is that groups tend to seek compromises before deciding on a course of action, and those compromises lead to unexceptional, uncreative, “safe” decisions. Questioning sessions can avoid this latter pitfall because the group isn’t committing to a course of action. You don’t need to compromise on a decision, because no decision is being made yet.)

It may seem like Berger’s method would only generate problems and not solutions. However, Berger urges you to remember that questions themselves—especially “what if?” questions—can directly lead to solutions. That’s why, 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.

“Question-Storming” Versus Brainstorming

Berger’s “questionstorming” sessions may not be too dissimilar to some brainstorming sessions—arguably, the only major difference is that participants phrase all of their thoughts as questions.

For comparison, in Purple Cow, Seth Godin explains his process for brainstorming a remarkable new product or idea:

1. Come up with the most extreme ideas possible. For example, if you’re brainstorming how much to charge for a product, the most extreme possible price is “free.” This parallels Berger’s “why not?” questions—“Why not give our product away for free?”

2. Determine which of those ideas will get you the results you want and how close you can come to that idea. Clearly, giving away a product for free won’t generate any profit—but how low could you make the price? This parallels Berger’s “what if?” questions—“What if we only charged people for the cost of production? What if we gave a cheap product away for free to attract new customers?”

3. Figure out how you can turn that idea into reality. This step is identical to Berger’s “how?” questions.

Ask Questions to Find Fulfillment

Questions aren’t only useful in business. Berger says that asking questions about your own life can help you discover what makes you happy or your purpose in life.

Consider activities that take up a lot of your time like work, school, or a particular hobby. Over time, those activities simply become habits, so it’s worth periodically asking yourself, “Why am I doing this?” Answering that question honestly helps you learn whether you truly find that activity rewarding—or if you’re doing it for a less fulfilling reason, such as habit or because it’s expected of you.

(Shortform note: When following Berger’s advice here, you might find that you don’t know why you’re doing something. Some studies have shown that practicing mindfulness—paying attention to your thoughts and feelings without trying to control them—can help you to understand your personality and motivations. Meditation is a common way to practice mindfulness; just five minutes of mindfulness meditation each day can help you to connect with your inner thoughts and cultivate better self-understanding.)

Another powerful question Berger suggests asking is, “What if I changed just one thing about my life?” Such questions are especially useful for breaking out of old routines and habits, as well as finding new ways to seek fulfillment.

For example, what if you cooked just one healthy meal each week? What if you read a book before bed, instead of scrolling through social media? What if you volunteered for a cause you believe in?

How Small Changes Add Up

It may not seem like making one change could make much of a difference to your sense of fulfillment and happiness. However, some experts argue that small adjustments create larger impacts than you might think.

In Atomic Habits, James Clear says that forming small, helpful habits can add up to big changes in your life. He explains that behaviors compound on themselves: Doing the same positive behavior over and over creates ever-increasing benefits. For example, saying one nice thing to your spouse won’t have a huge impact on your marriage; however, if you get into the habit of paying your spouse a compliment every day, you’ll greatly strengthen your relationship.

In The Power of Habit, productivity expert Charles Duhigg adds that changing one of your habits can trigger a chain reaction that encourages you to change other habits. For instance, improving your sleep habits will give you more energy, which could make you more motivated to exercise—and getting more exercise, in turn, will help you sleep better at night.

The Question That’s Key to Finding Happiness

Finally, Berger says that while asking questions can help you find added fulfillment in your life, this practice can also help you to be happy with the life you have right now. The key question to ask yourself is, “What am I grateful for?”

(Shortform note: Some research supports the idea that practicing gratitude increases your happiness. For example, a 10-week study on gratitude divided people into three groups. One group was asked to write a few sentences each week about good things that had happened to them, the second group was asked to write about bad things that happened each week, and the third was simply asked to write about significant events, whether good or bad. At the end of the 10 weeks, people in the first group (who wrote about what they were grateful for) were significantly happier and more hopeful than the people in the other two groups.)

Berger writes that while “What am I grateful for?” isn’t one of the fundamental questions, it did emerge from a fundamental question posed by filmmaker Roko Belic: “Why are people who struggle with poverty or other hardships often happier than those who are more fortunate?”

(Shortform note: Belic may have been working with an incorrect assumption when posing this question. Some studies have shown that wealthier people are happier, at least up to a point. For instance, a study from 2010 concluded that the average person’s happiness increases with their annual earnings up to about $75,000 per year, at which point increased earnings have much less effect. A more recent study from 2022 said the cutoff point may be much higher—up to $500,000 in annual earnings.)

According to Berger, the answer to that question is gratitude. Struggling people tend to find happiness however they can—for instance, by spending time with their loved ones or volunteering for causes they believe in. On the other hand, wealthy people tend to obsess over acquiring more wealth or more possessions.

In other words, the happiest people aren’t those who have the most “stuff” but those who appreciate what they have. Berger concludes that regularly asking yourself what you’re grateful for is an effective way to recognize and appreciate what you have.

Get Off the Hedonic Treadmill

Following Berger’s advice and practicing gratitude may help you overcome a phenomenon that psychologists call the hedonic treadmill. This “treadmill” is an endless cycle of chasing what we think will make us happy, experiencing a brief moment of pleasure from attaining it, and then chasing the next thing when the pleasure wears off. Psychologists call it a treadmill because we’re constantly “running” after happiness, but we keep winding up in the same place emotionally.

Berger’s suggestion of practicing gratitude is one way to break out of this cycle—learning to be happy with what you already have helps you control the urge to chase after more “stuff.” To further help you escape the cycle, here are two other strategies:

1. Before buying something new, stop and ask yourself “Do I really need this, or do I just want it?” If you don’t need it, wait a few days and see if the urge to buy it starts to go away. Remember, you can almost always buy it later.

2. Find pleasure in simple things. You can find contentment and tranquility without spending money or a great deal of effort. Instead of always chasing after big, showy possessions and accomplishments, try enjoying the simple pleasures of taking a walk or watching your favorite TV show.