Derek Sivers
How to Know a Person - by David Brooks

How to Know a Person - by David Brooks

ISBN: 9780593230077
Date read: 2025-11-26
How strongly I recommend it: 8/10
(See my list of 430+ books, for more.)

Go to the Amazon page for details and reviews.

First part was great - so empathetic - about how and why to really get to know someone. I skipped the middle part about difficult conversations in the Culture Wars. Last part was great, about what it is to be wise.

my notes

Sure it works in practice, but does it work in theory?

Building a friendship or creating a community involves performing a series of small, concrete social actions well:
* revealing vulnerability at the appropriate pace
* being a good listener
* end a conversation gracefully
* ask for and offer forgiveness
* let someone down without breaking their heart
* sit with someone who is suffering
* host a gathering where everyone feels embraced
* see things from another’s point of view.
All these different skills rest on one foundational skill: the ability to understand what another person is going through.

See someone else deeply and make them feel seen.
Accurately know another person, to let them feel valued, heard, and understood.

The #1 reason people don’t see others is that they are too self-centered to try.
“I’m all about myself. Let me tell you my opinion. Let me entertain you with this story about myself.”
Many people are unable to step outside of their own points of view.

Illuminate them with a gaze that is warm, respectful, and admiring.
Offer a gaze that says, “I’m going to trust you, before you trust me.”
A gaze that says, “I want to get to know you and be known by you.”

Resist the urge to project your own viewpoint.
Do not ask, “How would I feel if I were in your shoes?”

Morality is mostly about how you pay attention to others.

We are constantly representing people to ourselves in self-serving ways, in ways that gratify our egos and serve our ends.

look at everyone with a patient and discerning regard,

Inspiration knocks softly and then goes away if we don’t answer the door.

Offer the kind of attention that can change people.

90% of life is just going about your business: supermarket, small talk while there are other people around.
In these normal moments of life, you’re not staring deeply into another’s eyes or unveiling profound intimacies.
You’re just doing stuff together - not face-to-face but side by side.
You are accompanying each other.
When you’re first getting to know someone, you don’t want to try to peer into their souls right away.
It’s best to look at something together.
Not studying a person, just getting used to them.
Getting a sense of each other’s energy, temperament, and manner.
Subtle, tacit knowledge about each other that is required before other kinds of knowledge can be broached.
Becoming comfortable with each other, and comfort is no small thing.
Until the situation feels safe and familiar.

Be willing to let the relationship deepen or not deepen, without forcing it either way.
Act in a way that lets other people be perfectly themselves.
Patience: Trust is built slowly.

People are more fully human when they are at play.
Play isn’t an activity; it’s a state of mind.

Accompaniment is a humble way of being a helpful part of another’s journey.
Let others voluntarily evolve.

Writers are at their best not when they tell people what to think but when they provide a context within which others can think.
Man listens more willingly to witnesses than teachers, and if he does listen to teachers, it’s because they are witnesses.

An extrovert walks into a party and sees a different room than an introvert does.

A person is a point of view.
We take the events of life and, over time, create a very personal way of seeing the world.
Each person takes the experiences of a lifetime and integrates them into a complex representation of the world.
A distinct way of seeing.
People don’t see the world with their eyes; they see it with their entire life.

Someone who can tell funny stories?
That’s a raconteur, but it’s not a conversationalist.
Someone who can offer piercing insights on a range of topics?
That’s a lecturer, but not a conversationalist.
A good conversation sparks you to have thoughts you never had before.

There is a “novelty penalty” when we speak.
People have trouble picturing and getting excited about the unfamiliar, but they love to talk about what they know.

People aren’t specific enough when they tell stories.
They tend to leave out the concrete details.
But if you ask them specific questions...
(“Where was your boss sitting when he said that? And what did you say in response?”)
... they are likely to revisit the moment in a more vivid way.

The experience of being listened to all the way on something - until your meaning is completely clear to another human being - is extremely rare in life.

Nobody escapes high school. Whatever your high school fears were, they are still there.

Asking good questions can be a weirdly vulnerable activity.
You’re admitting that you don’t know.
Sometimes a broad, dumb question is better than a smart question, especially one meant to display how well-informed you are.
The worst kinds of questions imply, “I’m about to judge you.”

Encourage the other person to take control and take the conversation where they want it to go.

Big questions interrupt the daily routines people fall into and prompt them to step back and see their life from a distance.

* “What crossroads are you at?”
* “If you died tonight, what would you regret not doing?”
* “Can you be yourself where you are and still fit in?”
* “What is the no, or refusal, you keep postponing?”
* “What have you said yes to that you no longer really believe in?”
* “What forgiveness are you withholding?”
* “How have you contributed to the problem you’re trying to solve?”
* “Tell me about a time you adapted to change.”
* “What’s working really well in your life?”
* “What are you most self-confident about?”
* “Which of your five senses is strongest?”

People are longing to be asked questions about who they are.

Social disconnection warps the mind.
When people feel unseen, they tend to shut down socially.
People who are lonely and unseen become suspicious.
They start to take offense where none is intended.
They become afraid of the very thing they need most.
People become proud of their bitterness.
To be moral in this world, they think you just have to feel properly enraged at the people you find contemptible.
It’s a sadistic striving for domination.
Love rejected comes back as hatred.

As a society, we have failed to teach the skills and cultivate the inclination to treat each other with kindness, generosity, and respect.
How to restrain their selfishness and incline their heart to care more about others.
How to find a purpose, so their life has stability, direction, and meaning.
Basic social and emotional skills so you can be kind and considerate to the people around you.
The breakdown in basic moral skills produced disconnection, alienation, and a culture in which cruelty was permitted.

If you want to know someone well, you have to see the person in front of you as a distinct and never-to-be repeated individual.
But you’ve also got to see that person as a member of their groups.
And you’ve also got to see their social location - the way some people are insiders and other people are outsiders, how some sit on the top of society and some are marginalized to the fringes.
The trick is to be able to see each person on these three levels all at once.

Every conversation takes place on two levels: the official conversation and the actual conversation.
The actual conversation occurs in the ebb and flow of underlying emotions that get transmitted as we talk.
With every comment you are either making me feel a little more safe or a little more threatened.
With every comment I am showing you either respect or disrespect.
With every comment we are each revealing something about our intentions:
“Here is why I am telling you this. Here is why this is important to me.”

Every conversation exists within a frame: What is the purpose here? What are our goals?
A frame is the stage on which the conversation takes place.
I should have stayed within her frame a little longer, instead of trying to yank the conversation back to my frame.
The person who is lower in any power structure than you are has a greater awareness of the situation than you do.

The achievements which society rewards are won at the cost of a diminution of personality.

Get into narrative mode.
Don’t ask, “What do you think about X?”
Instead, “How did you come to believe X?”
This is a framing that invites people to tell a story about what events led them to think the way they do.
Don’t ask people to tell their values.
Instead, “Tell me about the person who shaped your values most.”
“Where’d you grow up?”
“When did you know that you wanted to spend your life this way?”

Ask about intentions and goals.
I’m asking myself as people tell me their stories: What’s the plot here?
I’m not just listening to other people’s stories; I’m helping them create their stories.

Culture is a shared symbolic landscape that we use to construct our reality.

People who are descended from those who practiced plow-heavy agriculture tend to live in cultures that have strongly defined gender roles, because it was mostly men who drove the plow.
People who are descended from those who did non-plow farming tend to have less defined gender roles.
People descended from sheepherding cultures tend to be individualistic, because a shepherd’s job requires him to go off on his own.
People descended from rice-farming cultures tend to be very interdependent, because everybody has to work together to raise and harvest rice.

For Jews, argument is a form of prayer.

When I’m trying to know you, I’m going to want to ask you how your ancestors show up in your life.
That means asking certain key questions:
* Where’s home?
* What’s the place you spiritually never leave?
* How do the dead show up in your life?
* How do I see you embracing or rejecting your culture?
* How do I see you creating and contributing to your culture?
* How do I see you transmitting your culture?
* How do I see you rebelling against your culture?
* How do I see you caught between cultures?

WISE PEOPLE:
Wise people don’t just possess information; they possess a compassionate understanding of other people.
Wise people don’t tell us what to do; they start by witnessing our story.
They take the anecdotes, rationalizations, and episodes we tell, and see us.
They see the way we’re navigating the dialectics of life - intimacy versus independence, control versus uncertainty - and understand that our current self is just where we are right now, part of a long continuum of growth.
They’re really good confidants - the people we go to when we are troubled - are more like coaches than philosopher-kings.
They take in your story, accept it, but push you to clarify what it is you really want, or to name the baggage you left out of your clean tale.
They ask you to probe into what is really bothering you, to search for the deeper problem underneath the convenient surface problem you’ve come to them for help about.
Wise people don’t tell you what to do; they help you process your own thoughts and emotions.
They enter with you into your process of meaning-making and then help you expand it, push it along.
Wise people create a safe space where you can navigate the ambiguities and contradictions we all wrestle with.
Receptivity, the capacity to receive what you are sending.
Creating an atmosphere of hospitality,
Free to be yourself, encouraged to be honest with yourself.
Wise people help you come up with a different way of looking at yourself, your past, and the world around you.
Very often they focus your attention on your relationships.