#language #communication

Real talk, this could be 5 or 6 pages but I've put everything here.

Conversations

Be a engaged listener. Watch for the body language if the other person wants to speak (or end the conversation entirely). Many conversations go on longer than either party wants.

Leave the other person wanting more, not less. If you're meeting someone at a social event (like a party) and you talk for 30 minutes before making an excuse, you're more interesting than if you talk for 3 hours.

Ask follow up questions, and open-ended ones. Don't make it sound like an interview. If conversation lulls, move on.

People like to talk about themselves and feel seen. Show interest.

"Say more about that"

Repeat back a word as an open ended prompt. "We went to Korea last summer" "Korea?"

Use people's names (but not too often)

FORD

Ask about Family, Occupation, Recreation, Dreams.

Avoid topics like religion, abortion, politics, economics.

Responsiveness

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Whenever the halal truck guy says something—anything—to her, she reacts as if she’s just heard the most delightful inquiry in her life, worthy of an equally thoughtful and delightful response. “You from Brazil?” is usually the kind of question that merits an apathetic “no” or a displeased “yeah.” She says “I am Brazilian! Yes! Oi!” with a theatrical wave of the kind issued by dignitaries on parade floats. He follows it up with by asking, ludicrously enough,  in an example of either low-quality banter or condescension, whether she knows Ronaldo—one of the most popular athletes in the world. She makes him look good by following it up with a joke about how “he’s my family member.” Talking with her is like dancing lead with a really good follow.

have a good friend who is somewhat similar to this TikTok person. People fall in love with her like I’ve never seen before with anybody. What she has, unlike a lot of Angeleno automata, is the same keen responsiveness. When you say anything at all, she turns her whole person towards you, and you are the fixed point of the universe. The moment after you speak, she replies in a way that makes it clear she’s listened to you with every ounce of her.

There’s a guy in publishing I place in this category, a person who you’d never select as “the charismatic guy” from a lineup. He is remarkably compelling, largely because he seems captivated by everyone and everything around him. Everywhere he goes, there is more ambient energy. He is almost universally desired and liked, and he’s enjoyed a kind of meteoritic success that makes people suspicious until they meet him and are charmed like everyone else.

Everyone wants to know how to be liked. But I think we all know, actually, how to be liked, it’s just that it’s hard. It takes attention and openness, and the confidence to present your character like it’s a fun mask you’re wearing rather than a lesson you’re desperate to teach someone. If you have that, it’s simple: when people put energy into you, attune to it, and give them harmonious energy back.

"If you put behavior into the world, you get behavior out.”
Responsiveness is a core human need/desire. It is, perhaps, required for happiness. People are happy enough rich, and people are happy enough poor. But it’s hard to imagine anyone happy without a feeling that their actions have some impact, however small. Even if you’re not going to be remembered by history, you want to be remembered by your barista. The prisoner, though largely robbed of power, is probably happier if he can vex his captors, or skirt the rules somehow. Life is good if it squishes nicely when you poke it.

Burnout is a failure of responsiveness

A major factor in burnout is “broken steering”: people feeling, for a long period of time, that their efforts to exert control don’t do anything. They show up to work, click their mouse, make suggestions, and nothing happens, and it’s hard to tell if their work ultimately matters. There is a classic phrase for this—being a “cog in the machine.” But there are even worse feelings than being a cog—at the very least, that role involves the transfer of mechanical energy. What’s worse is just feeling like a banana lying in the dust.

Video games are pure responsiveness and clarity

Grasping for responsiveness is responsible for a lot of chaos. When relationships are locked in a seemingly unbreakable pattern, paramours cause drama. When people feel imprisoned by an impersonal environment, they vandalize. When the downtrodden feel that the political system doesn’t represent their interests, they elect lunatics who pretend to.

To Listen Well, Get Curious

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A common piece of interacting-with-people advice goes: “often when people complain, they don’t want help, they just want you to listen!”

For instance, Nonviolent Communication:✻

It is often frustrating for someone needing empathy to have us assume that they want reassurance or “fix-it” advice.

I've found it useful to ask people if they want empathy or solutions

Frequently the “just listen” advice comes with tactical tips, like “reflect what people said back to you to prove that you’re listening.” For instance, consider these example dialogues from Nonviolent Communication:§

Person A: How could you say a thing like that to me?

Person B: Are you feeling hurt because you would have liked me to agree to do what you requested?

Or:

Person A: I’m furious with my husband. He’s never around when I need him.

Person B: So you’re feeling furious because you would like him to be around more than he is?

I say this with great respect for Nonviolent Communication, but these sound like a 1970s-era chatbot.

This advice is similarly repeated in The Like Switch, and the negotiation MasterClass by the same author

Recently, I realized why people keep giving this weird-seeming advice. Good listeners do often reflect words back—but not because they read it in a book somewhere. Rather, it’s cargo cult advice: it teaches you to imitate the surface appearance of good listening, but misses what’s actually important, the thing that’s generating that surface appearance.

The generator is curiosity.

When I’m curious about what someone’s saying, I often do repeat things back to them in my own words. But it’s because I’m genuinely curious, not because I’m checking off the “reflect words” box in my “be a good listener” checklist. That means I do it in a way that sounds like my natural speech, instead of mimicking them like a chatbot.

When done this way, reflective listening feels validating rather than alienating. It’s a way of demonstrating that I care a lot about what someone has to say. Putting their idea into my own words shows them that I’ve fully digested it, and helps us establish a shared language in which to talk about it. That, in turn, makes the conversation fluent and collaborative, rather than a zigzag of bad assumptions and corrections.

So the right advice isn’t “listen harder and repeat everything back”—you won’t be genuine if you’re just imitating the surface appearance of a good listener. Instead, be humble and get curious! Remind yourself that there’s a ton of detail behind whatever you’re hearing, and try to internalize all of it that you can. Once you’ve done that, your advice will be more likely hit the mark, and you’ll be able to communicate it clearly.

Understand the other person

In each case, the “helper” tried to learn about the “complainer’s” reality in as much detail as possible—not just the problem, but the whole person and whatever else was behind the immediate issue. And that’s what made it possible for them to actually help.

It often feels like I understand enough to be helpful without knowing all those details. But when I think that, I’m usually wrong: I end up giving bad advice, based on bad assumptions, and the person I’m talking to ends up having to do a bunch of work to argue with me and correct my bad assumptions. That makes the conversation feel disfluent and adversarial instead of collaborative.

Intentionally Making Close Friends

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It’s easy to slip into a passive mindset here, to think of emotional connections as ‘something that take time’ or ‘need to happen naturally’. That to be intentional about things is ‘inauthentic’. I think this mindset is absolutely crazy. My close friendships are one of the most important components of my life happiness. Leaving it up to chance feels like passing up an incredible opportunity. As with all important things in life, this can be optimised - further, if done right, this adds a massive amount to the lives of me and of my future close friends.

One of the core parts of my life philosophy now is the skill of agency, of actually doing things. The skill of going out of your way to make opportunities. To identify what’s missing in my life, and in the world. Finding the actions that I don’t need to take, that no one else will make me take, or do for me, and deciding to take them anyway. Fixing that which is broken. Finding that which is not broken, and deciding to make it better anyway. Exploring and trying new things. Challenging my self-image and growing. Fundamentally escaping the mindset of needing permission, and breaking past the illusion of doing nothing. I think this is one of the most valuable skills anyone can learn, and one I cherish, though I am far from perfect at it. And this experience is a large part of why I value it. Not realizing I could make close friends was a failure of agency, an unknown-unknown that cut out a massive amount of potential happiness, without even realizing it.

One decent way of engineering an authentic 1-1 conversation is to go through a bunch of personal and vulnerability-inducing questions together, a la 36 Questions that Lead in Love (after cutting the ⅔ of questions that I found dull). So I made a list of questions I considered interesting, which I expected to lead to authentic and vulnerable conversations. And then went up to the 10-20 people I felt most friendly with, explained the experiment, and asked if they’d be interested in blocking out a few hours, and going through the list together.

Some of my favorites:

You can't just launch into these with strangers. Gotta set ground stage first or people will think you're strange.

I still somewhat cringe looking back on that. I think having a literal list of questions made the interactions much more artificial.

Advice

I argue for being much more intentional about social things than normal. When doing this, it’s easy to come across as cold and calculating. I think it’s super important to try to remain authentic, and to signal authenticity. I find it helpful to generally be friendly, make jokes, be honest and transparent, and be willing to be vulnerable. Eg, being open about the strategies I’m running and why, if it ever comes up.

This strikes me as robotic, even with the disclaimer.

Seek Excitement

A key mindset I use when forming connections via conversation is: “If we aren’t both excited about this conversation, do something differently”. This applies especially when talking to someone I don’t know well, and want to figure out whether we might become good friends.

Most social norms optimise for conversations that feel safe, not ones that feel exciting, so I need to do something differently! This means asking the other person questions. This means taking a genuine interest in what we’re talking about - and if I can’t take a genuine interest, then I am doing something wrong.

A tactic I find helpful here is what I call recursive curiosity. I lead by asking an open-ended question that invites a detailed answer. Then, I introspect and try to notice excitement, find the part of their answer I find most interesting, and ask a follow-up open-ended question about it. Then, I repeat this process on their new answer. After about 3-4 iterations, we’ve normally gotten somewhere that feels alive and novel, where we’re both learning, rather than the same stale conversations they have all the time. The follow-up questions don’t need to be thoughtful or elaborate, often just ‘[specific detail] sounds interesting, tell me more’ or ‘[specific detail] didn’t really make sense to me, can you clarify? Did you mean [naive interpretation]?’ are more than enough. Introspecting on confusion or curiosity also works well. Often, rather than having a clear purpose to my questions I try to maximise surface area - just asking questions that point at my confusions and try to maximise the new information I gain, and the amount that I learn. This tends to feel fairly reactive - just responding to whatever was most interesting in the last thing said.

Boring conversations

Sometimes I feel trapped in a boring conversation direction because the structure of small talk feels hard to break out of. When this happens, I like to go meta, eg observing ‘man, I feel like I keep having the same kinds of conversations at these places’ or ‘let’s get the boring questions out of the way - [standard small talk done rapidly]’. If they seem to empathize, this is a good opener for a more fun question, eg: ’what kind of things do you get excited about?’, ‘what’s something cool you learned recently?’, or ‘have you had any particularly memorable conversations in [this context]?’

Do something unexpected

I also find that both are effective for breaking people’s social scripts/default ways of acting by being weird and unexpected - I find this is often a good first step to actually having a meaningful conversation. I find that sharing anxieties and insecurities can work particularly well here - almost everyone has them, it feels stigmatized to discuss them but people tend to respect you when you do, and they’re often much more common and relatable than people think.

This is a very, very different mindset from standard social norms, which push me towards being bland and inoffensive, and minimising the probability of bad interactions. A bad interaction (so long as it doesn’t damage my reputation) is just as useless as a mediocre interaction for finding potential friends. Instead I want to maximise the probability that, if someone is compatible with me, we have an awesome interaction. This is a key part of why I push for excitement and vulnerability - many people won’t vibe with that, but it makes it much more likely that I hit it off with the right kind of person.

Warning: This logic does not apply with people who I will need to interact with regularly anyway, eg co-workers/classmates. Social norms around minimising weirdness/potential for bad outcomes make much more sense in those situations, since downside risk is much higher. These mindsets work best when eg meeting people at a party or meetup or friends of friends, where I won’t necessarily interact with them again.

Take Social Initiative

Follow up with people to arrange a meetup!

Keep in touch!

The author of this piece uses a spreadsheet and calendar to write down "reach out to so-and-so X days after our last chat". This feels a little too inauthentic for me, but I used to schedule texts months in advance, so pot/kettle perhaps.

Spend time together, pay attention to friends' interests

Make time together.

Don't be afraid of seeming weird, and honor the other person's norms and boundaries (re: bluntness, politeness, etc.)

My main tip is to avoid jumping to conclusions about the problem and what is needed, and instead to explore the problem more than feels necessary. I often explicitly ask ‘what kind of help are you looking for?’ - sometimes they want a solution, sometimes they just want to vent.

Making Normal Conversations Better

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Most conversations suck, especially between new people.

The majority of people, I think, want to connect with people and open up about something. Almost everyone is full of some vital matter they’d like to express but that exceeds the capacity of the average conversational venue.

Some people don't want to connect deeply, or not with you. That's fine! But some conversations can be made better.

But many conversations can be nudged in the direction of openness, spontaneous complexity, and shared emotionality. And a surprising number of conversations, thus encouraged, can become quite connective. These are the conversations where you’re likely to find yourself laughing, rambling excitedly, engaging in extended weird riffs, crystallizing old knowledge in new patterns, feeling comprehended, feeling loved, and, generally, having the sensation that you’ve temporarily stepped outside the walls around your being.

This wasn't intuitive:

The method of conversation I had for a bunch of my life was babbling about whatever I was interested in until my interlocutor wandered away. That’s how I did things, until I noticed, after a decade, that people don’t like this, and, what’s more, I didn’t like it. When, occasionally, I met people who managed to induce me to have a more connective conversation, I enjoyed myself much more than I would have if I’d set the tone.

Small Talk is Vital

I used to think that the way towards more genuine conversation was advancing the schedule of intimacy instantly by plunging into difficult, weird, or controversial topics, usually by asking some intense question, like, “what are you most afraid of.” I think lots of aspiring conversationalists—especially men—do this when they’re new to intentionally cultivating human connection. Essentially, this approach treats people’s barriers as a problem to solve. This is stupid.

That's not the point!

Some people get frustrated with small talk because the words themselves are not enlightening. But they’re focusing on the wrong thing. The spoken content of small talk is, it’s true, mostly vapid. However, the relevant information underneath the spoken content is fascinating if you learn to care about it. What you’re doing is mutually establishing tone and finding boundaries. You’re getting a sense of the person’s mood, energy level, vibe, willingness to talk to you, style of talking, and so on, and they’re getting the same from you. Also, it’s a basic sanity check. The person you’re talking to, implicitly, is assessing whether you can do basic social norms—in this case, small talk. If you can’t pull it off, it’s probably not safe for them to share anything beyond their feelings about the weather.

80% of the time, what you’re looking for is non-verbal, or barely verbal. “I’ve been okay lately,” spoken briskly, could mean nothing. With a pregnant pause, or a little facial tension, this could mean that they’re either totally not okay, or they’re happy and excited but want to downplay it. “Work has been insane lately,” said emphatically, could mean “I’m thrilled about my new startup” or “I’m reevaluating my priorities in life because I’m miserable.”

The best invitations are usually casual and vague, if you’re at the stage of a conversation where you’re establishing a connection, which can be anywhere between 2-15 minutes in. “Say more” and “care to elaborate” are magical phrases. You can also repeat what they said. “Work has been crazy lately.” “Work has been crazy lately?” That can do a lot. The question “why is that important to you,” while more intense, can get you really far, really fast, if you sense a mood of openness, especially if you learn to ask it casually.

But it has to be genuine or it will come off as robotic and false. You have to want to know.

Attention

People love attention, almost more than anything. Part of what makes people open up, conversationally, is the sense that someone is paying them more attention than normal. This is usually conveyed by shared body language, shared speech patterns, and granular responses — like, for an incredibly banal example, if someone tells you they used to live in Paris, you can say “I hear it’s beautiful, do you miss it” rather than, “oh cool.” Generally, treat people as if they’re important, and, if you can hack it, feel that they are important.

There's a balance. Too much attention too early puts them on the spot, or like an interview, or subservient (like if they're a fan of your work).

Non-verbals

The Power of Silence

A common conversational anxiety is the feeling that you need to fill every moment with sound, otherwise the person is going to get bored and walk away. But good, deep conversations usually contain silences where you can reorganize your thoughts or simply occupy the flow of time together.

You can signal that this is permissible, and thus that your interlocutor has space to relax into, by leaving good silence in a conversation: friendly silence where there’s some degree of maintained eye contact, receptive body language, and so on. Interestingly, I find that it’s often after these brief silences that conversations get profound.

Don't have to fill the space.

The meta level

Something that not a lot of people do, but that seems to work well for me, is noting properties of the conversation within the conversation. This creates a sense of shared space and mutual understanding. “It’s really nice talking to you,” works, or, “I didn’t expect this to get so intense,” or, “it’s great to connect about this,” or “okay here’s a funny question.” You’re pointing out that you’re another human being, feeling similar to how your interlocutor is feeling, which is not always obvious. It’s a dimension of affirmative language that’s one step beyond “I hear you” or “I see that.”

Monologues

Good conversations often contain moments that, on paper, look like monologues, which is to say, one person divulging something for a period of time, or telling a story. But the key thing is that they can’t feel like monologues.

There’s a marked difference between someone sharing something of emotional importance in a resonant way, and someone talking at you. The difference is attention: whether they’re weighing your reactions and modulating (consciously or subconsciously) their pace and tone to match where you’re at, whether they’re noticing if you’d like to interrupt with a question or comment, etcetera.

It’s pretty easy for cerebral, verbal people to lapse into monologue mode, myself included. The only real solution is awareness. Be aware of the potential and let it go when you’re doing it. That’s all you can do. When I find myself there, I tend to say something like “okay wow I’m talking a lot, what is your reaction to all of this,” and that lightens the mood and brings it back to the present.

Breaking up other people's monologues

To remedy this, beyond creating a connective environment as described above, you can signal that they’ve already earned your attention. A lot of the time, this looks like prosocial interruption— breaking the flow but in a kind way that makes them feel good (or, you could say, a way that raises their status). If they mention, on autopilot, that they like tactical shooting, you could say, “oh so you’re basically an action hero,” or ask them a question about that, or whatever. This indicates that you’re still interested in them if they go off-script or if the cadence is interrupted: they don’t need to do their song and dance.

Not sure about this one.

Other notes

Be surprised

If something floats across your mind that’s unexpected, like a conversational tangent jogs a memory or idea you didn’t foresee appearing, make it part of the conversation. “For some reason, this makes me think of [x]” is fine. Similarly, if your interlocutor says something that seems tangential or off-topic, ask them about it, encourage them to follow that path.

Talk about 50% of the time. Match their disclosure level.

Gently incline your current mood towards the mood of the conversation, rather than try to "wallpaper over yourself with whatever mood you think might be demanded."

This is good advice, but a hard skill to pull off. Can avoid being perceived as condescending, but risks being 'too flippant', etc.

People don't want to debate you, pretty much ever.

Don't always make everything about you and your stories.

Endings are good! "It was great talking with you, I'm going to XYZ."

Good Conversations have lots of doorknobs

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It's hard to improv an entire song, but if you can do a verse while another team member thinks of a chorus, it's an impressive trick.

"Take and take" of focus. Conversations can use the same technique.

Givers vs takers

Givers think that conversations are a series of invitations, while takers think that they're a series of declarations.
Like to like works well, but
If the two meet, frustration ensues: (why won't he ask me a question?) or (she thinks I'm interesting) or (why does he keep asking me about my boring job?)

Conversations need to keep moving.

Turn-taking is different in 1:1 vs multi person conversations.
Givers try to spark it laboriously: "let's all say our favorite thing about the show!" while takers just go ("That movie sucked grrr!")

If you never take the spotlight, your conversational partner has to do all the work. It's why "what's up?" is a terrible text to get. "entertain me!"

At this point the author uses the language of The Design of Everyday Things, except, as is common, conflates affordances and signifiers. Alas, the battle has been lost.

Good doorknobs invite conversation: I get creeped out when couples treat dogs like babies vs let me tell you about the plot of Air Bud.

Questions without doorknobs are bad ("What are you doing?" "How many living grandparents do you have?"), but questions with doorknobs are good ("Why do you think you and your brother turned out so differently?")

You can turn a 'bad' question into a handle: I have one living grandmother, and I think about how much knowledge she has that will be lost when she goes.

We like when people respond to us very quickly (see responsiveness, above).

People prefer hearing about mundane stuff we did together than exciting stuff we did apart (I went to Venice vs remember when we got stuck changing that lightbulb for 2 hours?)

Bad conversation is just telling people what's exciting to you.

The main reason we don’t create more affordances, however, is pure egocentrism. When we just say whatever pops into our heads, we may think we’re making craggy, climbable conversational rock walls, when in fact we’re creating completely frictionless surfaces. For example, I’m thrilled to tell you about the 126 escape rooms I’ve done, but my love for paying people $35 to lock me in a room blinds me to the fact that you probably do not give a hoot. I may even think I’m being generous by asking about your experiences with escape rooms, when my supposed giving is really just selfishness with a question mark at the end (“Enough of me talking about stuff I like. Time for you to talk about stuff I like!”).

See Also

Improv
Nonviolent Communication

It's not about the nail