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Notes From: The Book of Beautiful Questions

Here are my notes from The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead, by Warren Berger.




The simplest and most powerful thing that happens when we ask questions is that it forces us to think.


The goal of this book is to encourage a questioning habit. Our questioning ability is like a muscle. We need to use it and train it.


One reason people don't ask questions is the fear of revealing that they don't know something. This fear can be especially strong in the workplace.


If fear is the first enemy of questioning, running a close second is knowledge. The more you know, the less you feel the need to ask. We can easily fall into the trap of expertise, wherein knowledgeable people begin to rely too much on what they already know and fail to keep expanding upon and updating that knowledge. We don't know as much as we think we do.


The third and fourth enemies of questioning are bias and hubris.


If you lack humility, you'll probably do less questioning.


The last enemy of questioning is time. We just don't make time for questioning. We are conditioned to do, do, do, without asking why. The irony is that stopping to ask the right questions can prevent us from wasting time going down the wrong path.


We will be swamped with unreliable and false information for the rest of our lives, so we're going to need to rely on our built in bologna detectors, which run on questions. We should think critically about many of the decisions we make, not just political and consumer choices. Whether we accept a job offer, take a risk on a new venture, or opt to pursue a new calling, the same kind of rigorous thinking and questioning is needed. And while most of our everyday decision making is not as subject to outside influences, those decisions are subject to a distorting influence that comes from within - our cognitive biases. To make better decisions in all aspects of our lives, we must be aware of those biases and subject them to rigorous questioning.


Through questioning, we can more accurately assess risks, overcome irrational fears, and figure out what's in our long term best interest. We can detect bologna and ferret out phonies. We can begin to clarify what matters most to us and identify passions to pursue. We can do all of that by making better decisions, and we can do that by first asking better questions about those decisions.


5 all purpose questions for better thinking:

  • How can I see this with fresh eyes?

  • What might I be assuming?

  • Am I rushing to judgement?

  • What am I missing?

  • What matters most?


Our skillsets evolved to make quick decisions based on limited information, such as a rustling in the leaves, and when we follow those instincts while making decisions, it can lead us to respond more quickly than is necessary. We developed our cognitive sense to deal with a world that was much simpler in terms of the amount of new information and the pace of change. This resulted in a fixedness in the brain, and it doesn't serve us well today when we're making decisions. We're also a bit lazy cognitively speaking. We don't like to spend our mental energy entertaining uncertainty.


The path to better decision making begins by questioning one's own beliefs, biases, and assumptions. It's something people rarely do, and it's certainly not easy to do. There are some biases that are likely to remain invisible to us no matter how hard we search for them.


"Why do I believe what I believe?"


"What did I once believe that is no longer true?"


In questioning what you believe, don't overlook the desirability bias, which is quite powerful, perhaps even stronger than the much discussed confirmation bias. To figure out what your desirability bias is on any given issue, ask yourself this simple question: "What would I like to be true?" To much wishful thinking can crowd out critical thinking.


Think about whatever you believe on a particular issue, then consider that the opposite might be true. "What are some reasons that my initial judgement might be wrong?"


Questions to test your intellectual humility:

"Do I tend to think more like a soldier or a scout?" A soldier's job is to defend, while a scout's job is to explore and discover.

"Would I rather be right, or would I rather understand?" If you place too much importance on being right, it can put you in defense mode and close off learning and understanding.

"Do I solicit and seek out opposing views?" Don't ask others if they agree with you, ask if they disagree and invite them to say why.

"Do I enjoy the pleasant surprise of discovering I'm mistaken?" Finding out you were wrong about something is a sign of intellectual openness and growth.

"Why should I accept what I'm told?"


Critical thinking questions are designed to root out logical fallacies that may be based on faulty assumptions, or worse still, may be tricks designed to lead you to a false conclusion.


Use these five questions to detect BS:

  • "How strong is the evidence?"

    • "Does this evidence come from a solid source?"

    • "Is there an agenda behind it?"

  • "What are they not telling me?"

  • "Does it logically follow?"

  • "What is the opposing view?"

  • "Which of the conflicting views has more evidence behind it?"


Carl Sagan offered a list of 20 tricks to always watch for, including arguments that rely on authority, false dichotomies, and slippery slope arguments.


Since one of the keys to critical thinking is fair-mindedness, which is a willingness to consider multiple perspectives, critical thinkers are trained to ask, "what's the other side of this issue?"


We may chose to phrase a question in binary, yes/no, terms because it limits the possibilities we must consider. It makes it easier to decide. If you can change your closed question to an open question, it can profoundly alter the decision you're making.


To expand your range of thinking on a decision, ask "If none of the current options were available, what would I do then?" This questions forces you to consider new possibilities by temporarily removing existing ones.


Use these 5 questions to open up possibilities:

  • "How can I open up the question to be decided?"

  • "What is the great, the good, and the ugly?"

  • "If none of the current options were available, what would I do?"

  • "What is the counterintuitive choice?"

  • "What would an outsider do?"


There's a common problem evaluating the issue at hand because we're too close to it. A simple yet effective way to adopt a fresh perspective is by asking, "If my friend had to make this decision, what advice would I give?" We often give more sensible advice to others than we give ourselves.


Try distancing yourself from decisions about yourself by asking yourself questions in the third person. Or try asking what someone else would do, like Warren Buffet for example.


When you've decided to make an important decision, try to make it twice. Once, then make the same decision a day or two later.


Two questions to test the soundness of a decision are, "Is it possible to shoot holes in this decision?" And, "If I had to defend this decision at a later time, how would I do so?"


Courageous questions to overcome fear or failure:

  • "What would I try if I knew I could not fail?"

  • "What is the worst that can happen?"

  • "If I did fail, what would be the likely causes?"

  • "How would I recover from that failure?"

  • "What if I succeed? What would that look like?"

  • "How can I take one small step?"


Whether you're starting out or considering a possible change in direction, you can use targeted questions to try to get a better sense of what you're meant to do. Before looking at some of the questions designed to identify your true passion in life, it's worth considering a contrarian question: "Should I even be asking, 'what's my passion?'"


Passion is not something you follow, it's something that follows you as you put in the hard work to become valuable to the world.


Think about specific times when you've been at your best, then inquiring more deeply about those successful episodes. "What personal strengths did I display when I was at my best?" "Did I show creativity, good judgement, kindness?" "What are my superpowers?"


6 questions to help you find your passion:

"What is my tennis ball?" Identify the thing that pulls you. The thing that holds your attention as single-mindedly as a dog chasing a tennis ball.

"What makes me forget to eat?"

"What did I enjoy doing at age 10?"

"What are my superpowers?"

"In what way do I wish the world were different?"

"What is my sentence?"


These three ideas, that creativity matters to all of us, that we're all capable of being more creative in our work and our lives, and that there are basic steps we can take to stimulate our creativity and guide it toward productive results, are the focus of this section.


If you're trying to decide whether to pursue a project and want to make sure you're doing it for the right reasons, ask yourself, "What if I knew at the outset that there was no possibility of fame or fortune from this work? Would I still want to do it?"


It may seem that eureka moments come out of nowhere, but they don't come out of the blue. Your ability to make new connections is limited by the amount of knowledge you have. So if your goal is to be struck by new ideas you first have to do the relevant homework in whatever field you hope to be innovative. While doing research, focus on "why" questions to try to gain a better understanding of the issue at hand. "Why does this problem matter?" "Why does it exist in the first place?" "Why hasn't someone solved in already?" "Why might that change now?"


Museums are custodians of epiphanies.


"Am I rearranging the bookshelves?" Train yourself to recognize when you're using excess preparation to delay the scary inevitability of facing the big task at hand. "What can I do with what I have/know now?"


A creativity starting technique is to try to think of wrong ideas at the start of a project. In 180 degree thinking you start out by making something wrong and then see if you can turn that bad thing into something good.


When formulated and asked the right way, questions can enhance relationships. Questions show interest, create understanding, and build rapport.


Skip the advice. Ask these 7 questions to help someone figure it out for themselves.

  • "What is the challenge that you're facing?"

  • "What have you tried already?"

  • "If you could try anything to solve this, what would you try?"

  • "And what else?" Repeat 2-3 times as needed.

  • "Which of these options interests you most?"

  • "What might stand in the way of this idea and what can be done about that?"

  • "What is one step you could take to begin acting on this right away?"


"What can I learn from those I do not understand?"


Be humble about your biases, but also own them. "How might I own my own biases?" Try to factor in your biases when you take in new information or make judgements. "Knowing that I tend to lean in one direction, how might that be altering my view of this new information or situation?"


Having allowed the other person to state their case without judgement, ask for the same for yourself. "Can I briefly lay out for you what I think?" After you've made your case, try to immediately shift the conversation to a common ground discussion, as opposed to "let's take turns demolishing each others' arguments." Do this by using bridge questions that encourage people to find positive aspects and shared values within opposing arguments. "Can you find anything in your position that gives you pause?" "Is there anything in your position that you're attracted to or find interesting?" Be sure to answer both questions yourself at well.


When you and your partner disagree, try and see if you can articulate each others' feelings and perspectives. "Can I try to explain what I think your position is? And then you can do the same for me?"


Questions to ask your best bud:

  • "What do you struggle with on a day to day basis?"

  • "What have you always wanted to try?"

  • "If you could start your own non-profit, what would it be?"

  • "What would be the title of your autobiography?"

  • "If you had to live in another country for a year, where would that be?"


"What's the one thing, that if I did it differently, would make a difference to you?" "What is most important on your list of things to accomplish today, and is there any way I can help?"


One of the best questions a manager can ask their employees is, "What questions do you have for me?"


"Why do I choose to lead?" "How do I want to leverage my special talents and interests to make the world a better place?"


"Can I learn to keep learning?" "Am I courageous enough to abandon the past?"


"If we disappeared tomorrow, who would miss us?"


"What do we do that other organizations can't or won't do?"


"What is the one thing I can do that would make everything else easier or unnecessary?"


As you formulate your own beautiful questions, keep in mind these 3 main themes from the book. They may help you as you craft your own questions.

  • First, assumption-busting is one of the first and most important jobs to be done.

  • Second is the shifting of perspective. Either from another person's point of view, or a different time perspective.

  • Third is the counterintuitive effect. Think about the opposite of what is expected.


Challenging assumptions, shifting perspectives, and considering opposites are worth keeping in mind as you think of new questions to add to your list.


In order to do more questioning you must confront the enemies of questioning: fear, knowledge, bias, hubris, and time.

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