• Toby Sinclair

A More Beautiful Question Summary by Warren Berger

Updated: Jul 17

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⭐ Rating: 9/10 - Recommended For: Leaders and Managers


3 Big Ideas from A More Beautiful Question 💡


  1. The best businesses “run on questions”. Studies have shown that the most creative, successful business leaders have tended to be expert questioners. Questions are spades that help to unearth buried truths. One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking. Answers, on the other hand, often end the process.

  2. Despite their power, many businesses do not encourage questions. In fact, they actively discourage it. Asking questions can be perceived as a sign of weakness. Of not being informed. Leaders face a challenge in shifting from a commanding, know-it-all culture to one of curiosity.

  3. People think of questioning as simple, but it’s a very sophisticated, high-level form of thinking. Leaders must learn not only to ask more questions but also to ask the right kind. The most common type of question in business are closed questions (How many? How much? How fast?). Leaders must learn to ask the more sophisticated open questions (Why? What if? How?) to thrive in an environment that demands a clearer sense of purpose, a vision for the future, and an appetite for change.



2 Best Quotes from A More Beautiful Question by Warren Berger 💬


A beautiful question is an ambitious yet actionable question that can begin to shift the way we perceive or think about something—and that might serve as a catalyst to bring about change. Google cannot easily anticipate or properly answer these questions for you.

We face a “certainty epidemic”—wherein many people overestimate their knowledge, put too much faith in their “gut instinct,” and walk around convinced they have more answers than they actually do. If you feel this way, you’re less likely to ask questions.

A More Beautiful Question Summary


Tobys Top Takeaway


The best businesses run on questions.

Despite their power, in many workplaces questions are not encouraged.

Five reasons why people don’t ask questions.

  1. Questions can be seen as “inefficient” by many business leaders, who are so anxious to act, to do, that they often feel they don’t have time to question just what it is they’re doing.

  2. Questions can be hazardous to one’s career: to raise a hand in the conference room and ask “Why?” is to risk being seen as uninformed.

  3. Questions challenge authority and disrupt established structures, processes, and systems, forcing people to have to at least think about doing something differently.

  4. Questions require leaders to give up control. That they might not have all the answers. Or that others might come to an answer that they fear.

  5. Questions can make people impatient and even uncomfortable. The answers might lead to places they don’t want to go.

To overcome these barriers requires skill and bravery.

You can lead the way. By becoming a master questioner.

In fact, I’d argue you cannot lead well unless your master the ability to ask great questions.


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Big Ideas Expanded 💡



What If You Asked More Questions?


The best businesses “run on questions”. Studies have shown that the most creative, successful business leaders have tended to be expert questioners.


There are many examples of leaders who asked questions that led to breakthroughs.


Questions are spades that help to unearth buried truths. One good question can give rise to several layers of answers, can inspire decades-long searches for solutions, can generate whole new fields of inquiry, and can prompt changes in entrenched thinking. Answers, on the other hand, often end the process.


The industrial economy was all about knowing the answer and expressing confidence. If you did your homework, you were supposed to know. If you had unanswered questions, that meant you did a bad job and wouldn’t get rewarded. The problems faced by leaders today are very different. There is rarely “one right answer”. This is where questions help. They act like a flashlight illuminating possible options and guiding the way. Better questions lead to better results. If we think of “questions” and “answers” as stocks on the market, then we could say that, in this current environment, questions are rising in value while answers are declining.


Why Don’t Leaders Ask More Questions?


A recent study found the average four-year-old British girl asks 390 questions a day; the boys that age aren’t far behind. As you grow older, the number of questions drops dramatically.


Most business leaders aren’t asking enough questions, especially the right kinds of questions.


Few companies encourage questioning in any substantive way. There are typically no departments or training programs focused on questioning; no policies, guidelines, best practices. On the contrary, many companies—whether consciously or not—have established cultures that tend to discourage inquiry in the form of someone’s asking, for example, Why are we doing this particular thing in this particular way?


Five reasons why questions aren’t so common:


  1. Questions can be seen as “inefficient” by many business leaders, who are so anxious to act, to do, that they often feel they don’t have time to question just what it is they’re doing.

  2. Questions can be hazardous to one’s career: to raise a hand in the conference room and ask “Why?” is to risk being seen as uninformed.

  3. Questions challenge authority and disrupt established structures, processes, and systems, forcing people to have to at least think about doing something differently.

  4. Questions require leaders to give up control. That they might not have all the answers. Or that others might come to an answer that they fear.

  5. Questions can make people impatient and even uncomfortable.


If you don’t have that disposition to question you’re going to fear change. But if you’re comfortable questioning, experimenting, and connecting things—then change is something that becomes an adventure.


How Can You Ask Better Questions?


I’m always searching for a question that is hard (and interesting) enough that it is worth answering and easy enough that one can actually answer it.

Edward Witten


People think of questioning as simple, but it’s a very sophisticated, high-level form of thinking.


We face a “certainty epidemic”—wherein many people overestimate their knowledge, put too much faith in their “gut instinct,” and walk around convinced they have more answers than they actually do. If you feel this way, you’re less likely to ask questions.


One of the many interesting and appealing things about questioning is that it often has an inverse relationship to expertise—such that, within their own subject areas, experts are apt to be poor questioners. The comfortable expert must go back to being a restless learner.


In the beginner’s mind, there are many possibilities, but in the expert there are few.


You don’t have to hold a position of authority to ask a powerful question. In some ways, it can be more difficult or risky for those in authority to question.


Business leaders who question have a blend of humility and confidence. They are humble enough to acknowledge a lack of knowledge, and confident enough to admit this in front of others.


Often the worst thing you can do with a difficult question is to try to answer it too quickly. When the mind is coming up with What If possibilities, these fresh, new ideas can take time to percolate and form.


To ask powerful questions you must:

  • Step back

  • Notice what others miss

  • Challenge assumptions (including our own)

  • Gain a deeper understanding of the situation or problem at hand, through contextual inquiry.

  • Question the questions we’re asking.

  • Take ownership of a particular question.


It’s becoming increasingly difficult for people to find time “to step back and ask a large question like, ‘What do I want from life, anyway?’”

Gretchen Rubin, author of The Happiness Project


Questions need space. A pause or an interruption in the meeting, a halt of “progress,” a quiet moment looking out the window on the bus. Often, these are the only times when there is time to question. Asking Why requires stepping back from “doing,” it also demands a step back from “knowing.”


When people fail to see what’s right in front of them, it’s often because “they stopped looking too soon.


Every time you come up with a question, you should be wondering, What are the underlying assumptions of that question? Is there a different question I should be asking?


The most common type of question in business are closed questions (How many? How much? How fast?). Leaders must learn to ask the more sophisticated open questions (Why? What if? How?) to thrive in an environment that demands a clearer sense of purpose, a vision for the future, and an appetite for change.



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