Daniel's been thinking about something we touched on earlier today, in that episode about how bilateral diplomacy gets scripted. We mentioned briefing books, and he's latched onto one detail in particular — the personality notes. The stuff that's not the formal agenda, not the policy positions, but the quiet observations about the human being on the other side of the table. That the person enjoys bird watching. That they have a specific sense of humor. That there are topics you should absolutely not bring up. He points out that this is essentially an intelligence-gathering process — foreign ministries actively curating personality dossiers on world leaders for future use — and asks whether this is a real, institutionalized thing. But he's also got a more personal angle here. He brings up his own experience of conversations with well-meaning relatives who don't know him well, where he's had to steer discussions away from his experience growing up Jewish in Ireland and the anti-Semitism he encountered — raw territory he'd rather not revisit in casual settings. His point is, if someone had quietly noted that preference in advance, those conversations would have been better for everyone. So he's asking: are these personality dossiers real, how do they work, and is there a way we can borrow from that practice in our own lives — building mental models of relationships, whether we write them down or not — that captures the useful parts without the weirdness?
They're absolutely real. And they're not even that secret — the existence of this practice is pretty well documented, it's just that nobody talks about the contents. Every foreign ministry has what amounts to a living file on every significant counterparty. The State Department calls them "scene-setter" memos or briefing memoranda. The British Foreign Office has been doing this for centuries — they have a whole taxonomy.
A taxonomy of people.
A taxonomy of what you need to know about a person before you're in a room with them. And it goes well beyond "enjoys bird watching." The depth is... look, when the Obama team was preparing to hand over to Trump in 2016, the transition briefing materials included extensive personality profiles. Not just policy positions — actual behavioral notes. How the incoming president processes information, what kind of arguments land with him, what triggers defensiveness. That's a domestic transition. Now imagine what a foreign ministry compiles on a leader they've been observing for twenty years.
So it's not just hobbies and dietary restrictions.
No, it's a full operational manual for the human being. The Wikileaks diplomatic cables gave us a glimpse of this, actually. Some of those cables were essentially personality assessments of foreign leaders — written by ambassadors who'd spent years interacting with them, filed back to Washington, and presumably incorporated into the briefing books for the next meeting. The cables described temperaments, decision-making styles, what flattery worked and what didn't, who had whose ear.
And the fact that those leaked and the world didn't end is interesting in itself.
Well, some of them were embarrassing. There was a famous cable where an ambassador described a certain leader as having a "thin skin" and being susceptible to flattery about his intellect. That made news for about forty-eight hours. But you're right — it wasn't explosive in the way you'd expect. Partly because the assessments were, frankly, accurate. Everyone already knew.
The dossier said what everyone in the room already thought but couldn't say out loud.
And that's the first thing to understand about this practice: it's not a spy operation in the traditional sense. Most of what goes into these files comes from direct observation over years of meetings. A diplomat sits down with a foreign leader, notices that they light up when someone mentions their grandchildren, files that away. Next meeting, different diplomat, same observation. Eventually it becomes an institutional fact: this person's grandchildren are a reliable icebreaker. It's not clandestine — it's just systematic.
So the "intelligence" here is mostly pattern recognition over time.
Largely, yes. Though there's a more formal component too. Most foreign ministries have something called a "protocol office" or "visits office," and their job includes compiling what's called a "program of the visit" — but that program document has annexes. One of those annexes is the personality brief. And the protocol office doesn't just write it from scratch each time. They pull from a central repository. Every meeting the leader has ever had with anyone from that country, every state dinner, every phone call — someone wrote a memo afterward, and the personality-relevant bits get extracted and filed.
This is starting to sound like a CRM for world leaders.
That is... not a bad way to put it. A customer relationship management system where the customers are heads of state. And the "account managers" are ambassadors who rotate out every three years, so the institutional memory has to live somewhere.
Which is the part that makes it necessary, right? If you don't write it down, it walks out the door when the ambassador retires.
That's exactly the argument for why this exists. Diplomats rotate. A new ambassador shows up in a country, they've read the files, they know that the foreign minister has a son with a medical condition and that the topic is sensitive, they know the president prefers meetings before eleven in the morning because he fades in the afternoon. That's not gossip — it's operational continuity. Without it, you're reinventing the relationship every three years.
And offending the same people in the same ways.
Right. Which brings us to the "do not discuss" list, which is what Daniel was really getting at. Every good personality brief has one. Sometimes it's obvious — don't bring up the corruption scandal, don't mention the estranged brother. But sometimes it's deeply specific and counterintuitive. A leader might be perfectly happy to discuss their country's human rights record but absolutely cannot abide questions about their university years. You'd never know that without the file.
Daniel's example was personal — not wanting to discuss anti-Semitism in Ireland. Something that wouldn't be obvious to a well-meaning relative but that he'd rather someone noted in advance.
And that's where the practice gets uncomfortable for people, because it feels manipulative. But I think Daniel's instinct is right — there's a version of this that's just being thoughtful at scale. If you're going to spend an hour with someone, and you know in advance that a certain topic is painful for them, avoiding it isn't manipulation. It's basic decency. The dossier is just how you scale basic decency across an institution where the person who knows the thing and the person who needs to know the thing are never in the same room.
Let's talk about what actually goes into these files, because I think people imagine something much more sinister than the reality.
The reality is surprisingly mundane, mostly. You'll get a section on family — names, ages, anything notable. A section on interests and hobbies — genuine ones, not the curated public version. A section on communication style: does this person want small talk first or do they want to get straight to business? Do they respond better to data or to narrative? Do they make decisions in the room or do they need to consult and come back?
The decision-making style one seems useful.
It's arguably the most important section. If you're trying to negotiate something, knowing whether the person across the table can actually say yes right now, or whether they need to take it back to a committee, changes your entire approach. Some leaders are decisive in the room; others are conduits to a process you'll never see. If you don't know which one you're dealing with, you can spend three hours extracting a "yes" that was never theirs to give.
And you've just wasted the meeting.
And you've frustrated them, because they can't tell you they can't decide — that would be losing face. So they nod along, and you leave thinking you've got a deal, and nothing happens. The personality brief is supposed to prevent exactly that.
What about the weirder stuff? The personal observations?
There's a famous example — and I'm going to be careful here because the specifics are contested — but the general shape of it is well-attested. A certain Middle Eastern leader was known to respond very poorly to being touched on the shoulder. A friendly gesture in many cultures, but for this person, it was a dominance challenge. That was in the briefing book. Every diplomat who met him knew: hands visible, no contact. Is that invasive to document? Maybe. Is it better than an ambassador accidentally triggering a diplomatic incident with a friendly pat? Absolutely.
It's the difference between gossip and a safety briefing.
That's a good way to frame it. Some of this is about safety — physical safety, psychological safety, the safety of the relationship. And some of it is just about not wasting time. If you've got forty-five minutes with a head of state, you don't want to spend the first twenty minutes accidentally stepping on landmines.
So how does the information actually get collected? You mentioned ambassadors filing reports, but there's got to be more to it.
Multiple streams. The primary one is direct diplomatic contact — every meeting produces a cable or a memo, and the author is expected to include personal observations. Then there's open-source intelligence — what's the person saying in interviews, what are they posting, what are their former colleagues saying publicly. Then there's liaison with allied intelligence services — "we're meeting your guy next month, anything we should know?" That's routine. And then there's the protocol advance teams.
The people who show up a week before the visit.
They're goldmines. They walk through the venue, they meet with the counterpart's staff, and they pick up all the unspoken stuff. The counterpart's assistant mentions that the minister prefers a certain kind of tea, or that they'll need a prayer break at a specific time, or that they've been having back trouble and would appreciate a chair with armrests. None of that is classified, but it all goes into the file.
The chair with armrests is a perfect example of something that seems trivial but actually communicates something important.
It communicates that you paid attention. That you saw them as a human being with a back, not just a policy position with a flag. And that's the entire point of the exercise. The personality brief exists to make the other person feel seen and respected — or, in the more cynical reading, to manufacture that feeling. But the outcome is the same either way.
Daniel's question was whether we can do this in our own lives without being weird about it.
I think we already do, just less systematically. You have a mental model of everyone you know well. You know which topics are off-limits with which friends. You know that one colleague hates being put on the spot in meetings and another thrives on it. You adjust your behavior accordingly. That's not manipulation — it's social cognition. The only difference is that you're not writing it down.
But maybe we should be, in some contexts.
There's an argument for it. Not for everyone — you don't need a dossier on your neighbor. But if you're in a role where you manage relationships across a large network, or if you have a terrible memory for personal details, keeping some kind of lightweight record is useful. I know people who keep a simple note on their phone — "met at the conference in March, has two kids, wife's name is Sarah, allergic to shellfish." Next time they see that person, they can ask about the kids by name and not accidentally order shrimp.
And the person feels remembered.
And the person feels remembered. Which is the entire point. The weirdness comes from the asymmetry — the fact that in diplomacy, one side has a file and the other side doesn't know it exists. But in personal relationships, if you're upfront about it, the asymmetry disappears. "I'm terrible with names and details, so I write things down after we talk — hope that's okay." Most people are fine with that.
The transparency changes the valence completely.
It does. The same practice, done secretly, feels like surveillance. Done openly, it feels like care. And that's the line that diplomacy walks constantly — the files are secret by necessity, because you can't exactly hand the foreign leader a copy of their own personality assessment. But the intent is the same. You're trying to be a better conversation partner.
Let's talk about what happens when these files go wrong. You mentioned the Wikileaks cables — were there cases where the assessments were just flat wrong?
Oh, constantly. The most common failure mode is projection. A diplomat from one culture assesses a leader from another culture through their own cultural lens, and gets it completely backwards. There's a well-known example from the Cold War where American analysts kept describing Soviet leaders as "inscrutable" and "hard to read" — which was partly a cultural gap in how emotion is displayed, not a personality trait.
So the file says "inscrutable" but the reality is "doesn't emote the way I expect."
And that bad assessment then shapes years of diplomatic encounters. Every new ambassador reads the file, shows up expecting inscrutability, and interprets everything through that frame. The file becomes self-reinforcing.
The other failure pattern has to be staleness.
People change. The leader who loved golf in 2010 has bad knees now and hasn't played in five years, but the file still says "avid golfer." You bring it up, and now you've reminded them of something they can't do anymore. That's worse than not knowing.
Or the "do not discuss" topic that stopped being sensitive a decade ago, and now you're awkwardly dancing around something they'd actually love to talk about.
Which is why the best foreign ministries treat these files as living documents. Every interaction updates the record. "Mentioned golf — seemed less enthusiastic than in previous meetings. May want to retire this talking point." That level of detail exists. It's granular.
I'm trying to picture the person whose job it is to write "seemed less enthusiastic than in previous meetings" about a head of state.
It's usually a junior foreign service officer, often someone in their twenties or early thirties, sitting in on the meeting to take notes. They're trained to capture not just what was said but how it landed. Body language, tone shifts, moments of visible engagement or disengagement. That note-taker is the entry point for most of what ends up in the personality file.
So there's a twenty-six-year-old somewhere whose job is to notice that the prime minister's eyes glazed over during the trade statistics.
And that observation, if it's consistent across three meetings, eventually becomes a line in the briefing book: "Responds poorly to extended data presentations. Prefer narrative framing with numbers as supporting evidence." Which is useful information that probably changed how that prime minister was briefed for the rest of his career.
The sloth in me appreciates the long time horizon of this. One note-taker's observation, filed away, shapes diplomatic encounters five years later.
The institutional patience of it is remarkable. Foreign ministries think in decades. The personality file on a rising opposition figure might sit mostly unused for fifteen years, and then they become prime minister and suddenly it's the most-read document in the building.
Okay, so we've established these are real, they're fairly comprehensive, they're mostly built from direct observation, and they serve a genuine operational purpose. Daniel's second question was about whether we can adopt something like this in our own lives. And I think the answer is yes, but with some important guardrails.
The guardrails are everything. Because the personal equivalent of a diplomatic dossier, done wrong, is just creepy. Done right, it's what good friends do naturally — they remember what matters to you.
So what's the difference between a mental model and a dossier?
I think it comes down to three things. First, consent and transparency. If you're keeping written notes on people, they should know you're doing it, or at minimum it should be the kind of thing they'd be fine with if they found out. Second, proportionality. The level of detail should match the depth of the relationship. A file on your spouse that rivals a State Department briefing book is... maybe not the healthiest thing. A few notes on a new colleague to help you remember their name and what they're working on — that's just being organized.
And the third thing?
Purpose. The diplomatic files exist to make interactions better for both parties. If your personal notes exist to manipulate people or gain advantage, that's a different enterprise entirely. The test is: would the other person, on reading your notes, feel cared for or feel managed?
That's a good test. "Feel cared for or feel managed."
And it's not always a bright line. But I think most people can tell the difference intuitively. If you're writing down that your friend is going through a divorce so you remember to check in, that's care. If you're writing it down so you can exploit their vulnerability in a negotiation, that's... something else.
Daniel's example was specifically about the "do not discuss" list. He said he wouldn't object to someone having a note not to bring up his experiences with anti-Semitism in Ireland. That feels like a clear case of the first category — it's a note that exists to prevent pain, not to exploit it.
And that's the part of the diplomatic practice that translates most cleanly to personal life. We all have topics we'd rather not discuss with certain people, or in certain contexts. The difference is that in diplomacy, someone's job is to know that in advance. In personal life, we usually find out by accidentally stepping on the landmine.
And then apologizing profusely while the other person says "no, it's fine" and it's clearly not fine.
Right. So the question becomes: is there a way to know without the landmine? And I think the answer is that you can ask. Not "give me a list of your traumas" — that's not a conversation starter. But in any relationship that's deepening, there's a natural moment where you can say, "Are there things you'd rather I didn't bring up?" Most people have an answer to that question, and they're relieved to be asked.
That's the transparent version of the dossier. You're just asking directly instead of compiling observations from third parties.
And it's better, honestly. The diplomatic version exists because you can't just call up the foreign leader and say "what should I not talk about?" But in personal relationships, you absolutely can. The dossier is a workaround for a constraint that doesn't apply to us.
What about the positive side? The "this person loves bird watching" part. How do we capture that without being weird?
That one's easier, because people usually tell you what they're interested in. The challenge is remembering it. And that's where lightweight note-taking can actually be a superpower. I know someone who, after every social event, spends five minutes jotting down what they learned about the people they met. Nothing invasive — just "Sarah's training for a marathon," "James's daughter just started college." Next time they see Sarah, they ask about the marathon. Sarah feels great. The note wasn't creepy because it was just... paying attention.
Writing down what someone told you about themselves isn't surveillance. It's listening.
That's the reframe. The diplomatic dossiers feel strange because we imagine them being compiled from secret sources. But the vast majority of what's in them came from the person themselves, in conversations over years. The "intelligence" is mostly just remembering what was said.
So the practice Daniel's describing — building mental models of relationships — is really just systematized listening.
With an emphasis on "systematized." Most of us listen and then forget. The system is what makes the listening stick. And the system doesn't have to be a dossier. It can be a note on your phone. It can be a habit of reviewing before you see someone. It can be as simple as, before a difficult conversation, taking sixty seconds to think: what do I know about how this person communicates, and what should I avoid?
The pre-meeting mental review. That's the personal equivalent of reading the briefing book.
And I'd argue most people already do a version of this before high-stakes conversations. You're about to ask your boss for a raise — you're thinking about their mood, their communication style, what arguments have worked with them before. That's a personality brief. You just wrote it in your head in the elevator.
The difference is that the diplomat's version is written down, reviewed, and updated across an institution. Ours is ad hoc and disappears the moment the conversation ends.
Which is fine for most purposes. Most of us aren't managing diplomatic relationships that span decades and outlast our own tenure. But for the relationships that do matter over the long term — family, close friends, key professional connections — there's a case for being a little more deliberate.
I'm thinking about the "do not discuss" list specifically. Daniel mentioned that he's had to steer well-meaning relatives away from painful topics, and that it's awkward when they don't get the hint. That's a failure of the mental model on their side, but it's also a failure of communication on his side. He knows what he doesn't want to discuss, but he hasn't told them.
And that's the asymmetry problem again. The diplomatic version works because one side does all the work of figuring out the boundaries. In personal relationships, that's exhausting and unfair. The better approach is to state the boundary. "I'd rather not talk about that" is a complete sentence. The other person doesn't need a dossier — they just need to be told.
But that's hard for a lot of people. Daniel's example is emotionally charged — saying "I don't want to discuss my experiences with anti-Semitism" in the middle of a family gathering is a heavy thing to drop.
It is. And that's where the advance work helps. If you can communicate the boundary outside the moment — in a quieter setting, without the pressure of a conversation already in progress — it's much easier. "Hey, just so you know, I'd rather not get into this topic when we're all together." That's not a dossier. That's just being clear.
And if you're on the receiving end, and someone tells you that, the appropriate response is "thanks for letting me know" — not "why not?" or "but I'm curious."
Right. The diplomatic briefing book doesn't include justifications for why a topic is sensitive. It just says "do not discuss." And the diplomat reads it and moves on. They don't demand to know the backstory. That's a norm we could import usefully into personal life.
Let's talk about the scale question. Daniel asked whether we can create mental models of relationships — plural. How many of these can one person reasonably maintain?
Dunbar's number hovers over this whole conversation. The anthropologist Robin Dunbar argued that humans can maintain about a hundred and fifty stable social relationships — that's the cognitive limit. Beyond that, you're not really tracking individuals anymore; you're tracking categories.
So the mental model approach breaks down past a hundred and fifty people.
Which is exactly why institutions need written files. A foreign ministry is tracking thousands of individuals across hundreds of countries. No single human brain can hold all of that. The dossier isn't a replacement for social cognition — it's an extension of it, past the point where social cognition stops scaling.
For an individual, though, a hundred and fifty is plenty. Most of us are managing a much smaller set of relationships that actually matter.
And for those, the mental model is usually sufficient. You don't need a file on your closest friends — you know them. The practice Daniel's describing is most useful for the middle tier: people you interact with regularly but don't know deeply. Colleagues, extended family, professional contacts. The people where a little bit of deliberate remembering goes a long way.
The Dunbar middle class.
For that tier, I think the most useful thing you can steal from diplomatic practice is the post-meeting debrief. Diplomats write up their meetings immediately afterward, while the details are fresh. Most of us walk out of a conversation and immediately start forgetting it. Taking two minutes to note what you learned — what mattered to them, what they're working on, anything you should remember — that's a small habit with a big payoff.
I do something like that, actually. Not for people — for ideas. If I have a good conversation, I write down the interesting threads before they evaporate.
Same practice, different focus. And it works because memory is unreliable. You think you'll remember the important stuff, but you won't. The act of writing it down is what makes it stick — even if you never read the note again.
The note is the process, not the product.
The value is in the attention you paid while writing it. The file on the other side is almost secondary.
If Daniel wanted to implement something like this — a lightweight personal version of the diplomatic personality brief — what would you tell him to actually do?
I'd say start with the relationships where the cost of getting it wrong is highest. For most people, that's family. Not because family relationships are transactional, but because they're the ones where small misunderstandings compound over decades. Know the topics that are tender. Know the communication styles that work and don't work. You don't need to write a dossier — but before a family gathering, it's worth thirty seconds of reflection. Who's going to be there, and what do I know about where they are right now?
The pre-gathering mental briefing.
Then after, the debrief. What did I learn? What surprised me? What should I remember for next time? That cycle — brief, engage, debrief — is the diplomatic method stripped down to its essentials. It works for state visits and it works for Thanksgiving dinner.
The scale is different but the structure is the same.
The structure is the same because the problem is the same. You're a human being trying to interact well with another human being, and you have limited information and a limited window of time. Anything you can do to arrive better prepared makes the interaction better for both of you.
I think the one thing I'd add is that there's a humility piece here that often gets missed. The diplomatic files exist because the institution knows it doesn't know everything. It's an admission of ignorance — we need to write this down because we will forget, we will misread, we will project. The file is a hedge against institutional arrogance.
The best briefing books are written with an awareness of their own limitations. "Based on our observations to date, subject to revision." The personal equivalent is holding your mental models lightly. You think you know what your brother-in-law cares about, but people change, and your model might be three years out of date. The file is a starting point, not a conclusion.
The moment you treat it as a conclusion, you've become the person who's still talking about golf to someone with bad knees.
Right. The file is a hypothesis. The conversation is the experiment. And you update the hypothesis based on what you learn.
The practice isn't "compile a dossier and trust it." It's "pay attention, write it down, stay humble, and update constantly."
Which is, honestly, just good relationship hygiene. The fact that diplomacy does it with more paperwork doesn't change the underlying principle.
Hilbert: It's more common than you're making it sound.
The practice?
Hilbert: The personal version. People keeping files on other people. I did a stint at a... it was a high-end concierge service, late nineties. Rich people who wanted things. We kept profiles on every client. Not just preferences — actual psychological profiles. What kind of flattery worked. What time of day they were pleasant and what time they were... not. Who in their family they actually liked versus who they felt obligated to.
That's a concierge service?
Hilbert: That's a concierge service that charges five figures a year. The service wasn't the restaurant reservations. The service was knowing that Mr. Albrecht tips badly when his wife is present because he doesn't want her to know how much money he has. So you don't put him in a position where tipping is visible.
How many clients did you have files on?
Hilbert: About four hundred active. Another two thousand in the archive — people who'd used the service once or twice. Each file was maybe eight to ten pages. Updated after every interaction.
Eight to ten pages per person.
Hilbert: Minimum. Some were thirty. The longer someone had been a client, the thicker the file. There was one woman — she'd been with the service since the seventies. Her file was basically a biography.
The clients knew you were keeping these?
Hilbert: They knew we remembered things. They didn't know the extent of it. Nobody asked. They just enjoyed the experience of dealing with people who seemed to know them perfectly.
That's the asymmetry again.
Hilbert: It worked. The clients were happy. The staff were less happy — reading files before every shift, updating them after. It was exhausting. But the clients thought we were mind readers. That was the product.
Do you still have any of those files?
Hilbert: No. Shredded when the company sold. Standard procedure.
What did you learn from doing that, though? About how to track this stuff?
Hilbert: Two things. One, most people are not that complicated. You think you need thirty pages, but really there are about five things that actually predict how an interaction will go. Mood, time of day, who else is in the room, whether they've eaten recently, and whether they feel respected. Get those five right and you're ninety percent of the way there.
And the second thing?
Hilbert: The second thing is that the file makes you lazy. You stop paying attention because you think you already know. The best concierges ignored the files and just talked to the person. The files were for the new people who didn't know how to read a room yet.
That tracks with what we were saying about holding the model lightly.
Hilbert: The model is a crutch. Useful when you're learning, dangerous when you think you've graduated.
You're saying the diplomatic practice is really a training tool, not an operational one.
Hilbert: I'm saying the file is for the junior foreign service officer who's never met the person. The experienced ambassador doesn't need it. They've done the meetings. They know.
But the ambassador rotates out. That's the whole reason the file exists.
Hilbert: Fair. I'm not saying don't keep them. I'm saying don't confuse the file with the person. The file is a photograph. The person is still moving.
That's a good line to land on. The file is a photograph. The person is still moving.
I think that's the answer to Daniel's question about whether we can borrow from this practice. Yes, but borrow the method, not the artifact. The method is: pay attention, write down what you learn, review before you engage, update after. The artifact — the dossier — is just the institutional version of that. For an individual, a few notes on your phone will do the same work.
The misconception people have about this practice is that it's inherently manipulative — that knowing someone's preferences and sensitivities in advance is a form of psychological warfare.
The reality is that it's mostly just remembering. The manipulation isn't in the knowing — it's in what you do with the knowing. If you use it to make the other person feel seen and respected, that's hospitality. If you use it to exploit them, that's something else. The file is neutral. The intent is everything.
Daniel, I think the short answer is yes, these files are real, they're more mundane than you'd expect, and the useful parts are absolutely portable to personal life — with the caveat that transparency beats secrecy every time. Ask people what they'd rather not discuss. Tell them you're writing things down if you are. And remember that the goal isn't to manage people. It's to show up prepared enough that you can actually be present with them.
The best briefing book in the world can't replace paying attention in the room. But it can sure make the room less of a minefield.
Thanks to our producer Hilbert Flumingtop for keeping this show running, and for the concierge files we will never stop thinking about.
This has been My Weird Prompts. If you want to send us your own questions — about diplomacy, about relationship dossiers, about anything else that's been rattling around in your head — you can reach us at show at my weird prompts dot com.
We'll be back soon.
