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Toby Sinclair

Summary: How To Know a Person by David Brooks

Updated: Nov 1

 

📚 Should You Read This?


Toby's Rating: 9/10


How to Know a Person by David Brooks is a profoundly reflective exploration of what it means to connect with others on a meaningful level. For leaders, it offers tools and perspectives to deepen workplace relationships, build empathy, and navigate conversations with authenticity. David provides a framework for leaders to foster a culture of understanding—valuable in today’s complex, often fragmented, work environments.


Toby Sinclair Book Summary Introduction
 

✅ Toby's Top Takeaway From How To Know a Person by David Brooks


Stop it with the bore bombs.


Being a mediocre conversationalist is easy. Being a good conversationalist is hard.


The challenge is the common view of what makes a good conversationalist.


It's easy to assume they are someone who tells funny stories, commands the rooms, and gives piercing insights.


I met someone like this earlier today.


The problem was that their stories were not funny, their insights were lecturing, and they didn't stop for a breath. I listened for ten minutes. Then, after a quick exchange, it happened again—another lecture.


I received what Calvin Trilling calls a "bore bomb": people who think they think the conversation is them giving you a lecture.


I'm not the kind of person to interrupt, so I try my best to listen. But frankly, after 10 minutes of a bore bomb, I start thinking about what's for lunch.


In contrast, a good conversationalist is a master at fostering a two-way exchange. They lead people on a mutual expedition towards understanding.


In How To Know a Person, David Brooks describes these communicators as illuminators. They see people in all their fullness. Different cultures have words for this way of being. The Koreans call it nunchi, the ability to be sensitive to other people's moods and thoughts. The Germans have a word for it: herenzbildung, training one's heart to see the full humanity in another.


David offers a straightforward way to illuminate a conversation.


Don't ask: What do you think about x?

Ask: How did you come to believe X?


This framing invites people to tell a story about what events led them to think the way they do.


Here is another example:


Don't ask: What are your values?

Ask: Tell me about the person who shaped your values the most.


Better questions don't mean you won't need to sit patiently and listen for ten minutes. However, the quality of the question reduces the chance of a bore bomb. The answers will be illuminating.


And if you are lucky, you will meet one of those special people who will ask you illuminating questions, too.


🤖 Turn This Book Into Action


Despite reading this book, I still have a problem. I’m not converting the knowledge into action. To solve this problem, I’m turning to the solution everyone is looking for at the moment: artificial intelligence. I’ve developed a set of AI tools to turn knowledge into action.



 

💡 3 Big Ideas From How To Know a Person by David Brooks


  1. Seeing Beyond the Surface - How to Know a Person introduces the concept of “Illuminators” and “Diminishers,” describing how we can either bring out the best in others or unintentionally minimise their worth. For leaders, “seeing” someone goes beyond surface-level interactions—it requires full presence, understanding someone’s context, and recognising their unique strengths. This approach creates a foundation for trust, allowing employees to feel genuinely valued.

  2. The Power of the Right Questions - Asking open-ended, meaningful questions is the key to truly understanding someone. These questions should invite storytelling and reflection, helping leaders uncover their team members' motivations, challenges, and values. Questions like “What’s something you care about that you feel isn’t understood?” open doors to empathy and deeper connections, shifting the dynamic from transactional to transformational.

  3. Addressing the Crisis of Disconnection - According to David Brooks, a “crisis of loneliness” increasingly isolates people, often manifesting as mistrust and disengagement in the workplace. Leaders who prioritise connection, foster inclusivity, and engage employees meaningfully help counter this isolation. He highlights the need to normalise vulnerability, inviting leaders to acknowledge personal struggles and allow others to do the same. This creates a foundation of mutual support and resilience.


 

💬 Best Quotes From How To Know a Person by David Brooks


David Brooks How To Know a Person Cover

Being an illuminator, seeing other people in all their fullness doesn't just happen. It's a craft, a set of skills, a way of life. Different cultures have words for this way of being. The Koreans call it nunchi, the ability to be sensitive to other people's moods and thoughts. The Germans have a word for it: herenzbildung, training one's heart to see the full humanity in another.


Being a mediocre conversationalist is easy. Being a good conversationalist is hard. As I've tried to understand how to become a better conversationalist, I've had to overcome weird ideas about what a good conversationalist is. Like. Many people think a good conversationalist is someone who can tell funny stories; that's a raconteur, but that's not a conversationalist. A lot of people think a good conversationalist is someone who can offer piercing insights on a range of topics. That's a lecturer, but not a conversationalist. A good conversationalist is a master at fostering a two-way exchange. A good conversationalist is capable of leading people on a mutual expedition towards understanding you.


I often find myself on the receiving end of what the journalist Calvin Trilling called "bore bombs", people who think they think the conversation is them giving you a lecture.


Be a loud listener: When another person is talking, you want to be listening so actively that you're practically burning calories.


Fin the disagreement under the disagreement: When arguing, the natural thing is to restate your point of view until the other person sees the issue the way you do. The more exciting thing to do is to ask why we disagree at heart. What is the value disagreement underneath our practical disagreement?


Around 2018, many books have been published tracing the catastrophic decline in social relationships. They have titles like Lost Connections, The Crisis of Connection and The Lonely Century. In different ways, they present us with the same baffling mystery: the thing we need most is relationships. The thing we seem to be stuck at Most is relationships. I


I left this hard conversation feeling like I should have done more to understand her point of view, but I also should have done more to assert my own. To clarify and explore any disagreements that we might have.


The first thing I learned is that prior to entering into any hard conversation, it's important to think about conditions before you think about content. What are the conditions in which this conversation is going to take place?


With every comment, you either make me feel a little more safe or a little more threatened. With every comment, I show you either respect or disrespect. With every comment, we reveal something about our intentions. It is the volley of these underlying emotions that will determine the success or failure of the conversation.


Curiosity is the ability to explore something, even in stressful and difficult circumstances.


The authors of Crucial Conversations observed that in any conversation, respect is like air. When it's present, nobody notices, but when it's absent, it's all anybody can think about


Dennis Profitt, a psychologist at the University of Virginia, studies perception. He wants to know how people construct their realities, sometimes at the most elementary level. For example, He has done extensive research on a curious phenomenon: people generally vastly overestimate how steep hills are, even in places like San Francisco, where the hills are, in fact, pretty steep. Profit was conducting experiments in which he asked groups of students to estimate the grades of various hills around the UVA campus. A hill on campus might actually have a 5% grade, but a typical participant would estimate that I had a 20% grade one day. Prophet took a look at the most recent batch of experimental data and was stunned to find that suddenly; the students had got much better at estimating the grade of a particular Hill. Prophet and his team delved into the mystery and discovered the latest batch of questionnaires had been filled out by members of the UVA women's varsity soccer team. The Hills didn't look so steep because they were extremely fit athletes who would have had little trouble walking up the hill.


How you see a situation depends on what you are capable of doing in a situation.


People with heavy backpacks see steeper hills than people without backpacks because it's harder to walk up the hill with a backpack. People who have just consumed energy drinks see less steep hills than people who have not. People who have listened to sad music see steeper hills than people who have listened to happy music. Overweight people see distances as longer than people who are not overweight. We project our individual mental experience into the world and, therefore, mistake it for the physical world, oblivious to the shaping of perception by our century, systems, personal histories, goals, and expectations. You


People vary widely in their ability to project empathy. The Psychologist Simon Baron Cohen, one of the leading scholars in his field, argues that there's an empathy spectrum and that people tend to fall within one of seven categories on it, depending on their genetic inheritance, the way life has treated them and how hard they've worked to become empathetic. At level zero, people can hurt or even kill others without any feeling at all. At level one, people can show a degree of empathy, but not enough to break their cube. Cruel behavior. They blow up at others and cause emotional damage without restraint. At level two, people are simply clueless. They say rude and hurtful things without awareness. At level three, people avoid social encounters when possible because it is so hard for them. At level four, people can interact easily with others, but they do not like it when the conversation shifts to emotional, personal topics. Level five people have many intimate friendships and are comfortable expressing support and compassion. Level six are people who are wonderful listeners and intuitive about other people's needs.


It's common for conversations to fall into the trap of comment-making conversations rather than storytelling conversations. The psychologist Jerome Bruner distinguished between two different modes of thinking, which he called the paradigmatic mode and the narrative mode. The paradigmatic mode is analytical. It's making an argument. It's a mental state that involves amassing data, collecting evidence and offering a hypothesis. A lot of us live our professional lives in the paradigmatic mode, making presentations, writing legal briefs, issuing orders and cobbling together opinion columns. Paradigmatic thinking is great for understanding data, making the case for a proposition, and analyzing trends and populations; it is not great for seeing an individual person. Narrative thinking, on the other hand, is necessary for understanding the unique individual in front of you. Stories capture the unique presence of a person's character and how he or she changes over time. Stories capture how thousand little influences come together to shape a life, how people struggle and strive, how their lives are knocked about by lucky and unlucky breaks. When someone is telling you their story, you get a much more personal complicated and attractive image of the person. You get to experience their experience.


When I'm conversing with someone now, I'm trying to push against that and get us into narrative mode. I'm no longer content to ask What do you think about x? Instead, I ask, how did you come to believe X? This is a framing that invites people to tell a story about what events led them to, the way that to think they the way they do similarly, I don't ask people to tell me about their values. Tell me about the person who shaped your values the most. This prompts a story.


📹 How To Know a Person by David Brooks Video





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