Story Time for CXOs
Story Time for CXOs
INT. EXECUTIVE CONFERENCE ROOM - MORNING
The room features exposed brick and floor-to-ceiling windows. Dominating the room: a table that seats fourteen and costs more than a Honda Civic. Catering: La Croix, untouched fruit, pastries no one will eat because ewww, carbs.
Twelve executives arranged around the table. Combined annual compensation: $15 million. Along the walls there is a second ring: VPs, Senior Directors. The courtiers. They have laptops open but no one is taking notes.
9:47 AM
SARAH (52, Director of Strategy, exhausted) stands at the screen. She advances to slide 3. She has known for some years that she should NOT read slides word for word. She also knows that no one in this room but her and her small staff have actually read this slide, or any of these slides. So, she reads it aloud. Almost word for word, but not quite.
The slide is on every laptop in the room. The same slide was also emailed to all attendees two days ago.
The CFO is checking his brokerage portfolio under the table. He thinks no one notices. Everyone notices.
9:52 AM
Slide 7. Sarah is still reading. The COO hasn’t looked up in four minutes. A VP along the wall is openly scrolling LinkedIn.
SARAH: “…and so our go-forward strategy is to…”
Everyone can hear but no one is listening. The words fill the room like Girl From Ipanema in the elevator.
10:03 AM
The CEO checks his watch. Then checks it again eleven seconds later.
10:14 AM
A hand goes up. MARK (38, VP of Product, annoyingly eager) asks a question.
MARK: “Have we thought about the integration timeline?”
Sarah smiles the smile of someone who has answered this question in the document no one read, debated by her small staff for the last two weeks.
SARAH: “Great question. We’ll get to that.”
She advances to slide 12. She reads it aloud. It answers Mark’s question. Mark nods like he’s hearing it for the first time. He is.
10:27 AM
The CFO speaks for the first time.
CFO: “I think we’re aligned.”
Heads nod but no one asks: aligned on what? The question would break the spell.
10:38 AM
The meeting ends. Laptops close. Bodies disperse. What was decided? No one knows. No document will record an outcome, because nothing was agreed (or disagreed) on. Positions were taken by no one. Objections were raised by no one. This is called being a team player.
Sarah gathers her laptop. She spent forty seven and a half hours writing the deck. It was performed in fifty-one minutes. It will never be opened again.
In the hallway, two executives peel off. They find a small conference room. The door closes.
This is the meeting after the meeting.
This is where the actual decision will be made.
FADE TO:
An inbox. Unread. The memo sits there, fully formed, carefully reasoned, completely ignored.
I watched this happen. I sat in those rooms. I did the math on hours burned while someone read bullet points aloud. I calculated the cost of 19 brains (20 if you count Allan) sitting idle while information that could have been absorbed in twelve minutes got stretched into an hour and a half.
Recently I realized: this is Cargo Cult Civilization, but for organizations.
The Thermodynamic Diagnosis
In Cargo Cult Civilization, I argued that the algorithmic feed is replacing your cognitive machinery with something cheaper. The feed found your brain’s minimum-energy path and paved it. Reaction replaced reasoning. You perform thinking (opinionated, confident, often reactive) without the metabolic cost of actual thought.
Organizations used to run on written artifacts. Memos. Staff papers. Decision briefs routed up and down a hierarchy. Writing that forced explicit assumptions, coherent causal chains, accountability over time.
Then something shifted. Between roughly 1975 and 1995 (and decisively in the 1980s) large organizations crossed a threshold. Decisions started happening live, in rooms. Documentation became retrospective. Authority became ambiguous and negotiated live, luchadors in blue suits.
Why did the meeting replace the memo? Cuz it’s cheaper.
It’s cheaper in cognitive effort, and cheaper in political exposure.
Writing is expensive! You have to think before you type. You have to structure an argument. You have to commit to a position in words that can be quoted back at you later. You have to be right, or at least marginally coherent, because the document persists.
Meetings optimize for other things (that damn Moloch is back): social alignment, power signaling, emotional consensus, and (critically) plausible deniability. You can gesture vaguely at agreement without anyone pinning down what was agreed. (More on this below.) You can nod at the right moments. You can look smart.
The organization that stopped requiring written justification before decisions didn’t become faster. It became dumber. It lost the self-feedbacking error-detection mechanism that writing provides.
(As an aside, and this belongs in a different essay: Writing often is the process of thinking itself. Not coincidentally, the act of developing software is, quite literally, synonymous with coming to understand the problem and solution domains. This seems important when we’re talking about tossing software construction out, as a human endeavor. But I digress…)
Writing is a constraint system.
Remove the constraint, and you don’t get freedom. You get fog.
The Meeting-Industrial Complex
At BigCo, meeting culture wasn’t a problem. It was the whole fucking operating system.
Alignment meetings. Meetings to schedule meetings. Meetings with no agenda, no action items, with dozens of people. Meetings to deliver information in one-way half-duplex form, as if email hadn’t been invented. Meetings where attendance was the deliverable.
And those Story Time sessions. Sweet Mama Pajama, those Story Time sessions.
Some document (usually pretty decent) would in fact exist. Someone would have done the work. But instead of trusting a roomful of expensive adults to read and respond asynchronously, we’d convene a ritual ceremony where the document got performed aloud while everyone performed rapt attention.
Because that’s what was really happening. The reading-aloud was cover for the real activity: gauging reactions, calibrating takes, figuring out which way the room was tilting before committing to a position.
The document was a prop. The meeting was a performance of decision making. But no actual cognition occurred.
DSM Checklist for Story Time Syndrome
You might be at a Story Time organization. Here is the diagnostic rubric:
All HIPPOs are booked. Forever. Not “busy this week.” Booked for the next six weeks solid, with a waiting list. The calendar isn’t a coordination tool; it’s gladiatorial combat. Bribe their assistant with food or your urgent strategic question will be addressed sometime in late Q3.
“I’ll find time on calendars.” This phrase, spoken aloud, as if locating seventeen minutes of overlapping availability across six executives is a quest requiring incense, candles and prayer. If you hear this said more than once a week…
Slide deck rodeo. There are forty slides with twelve presenters. Each person “owns” their three slides and reads them aloud, verbatim, while everyone else zones out until it’s their turn. No one has read the full deck. No one will. The deck is not a document; it’s a talking stick passed around the circle. Your turn, Allan.
Square-root participation. This is one of those meetings with thirty-six people where six people talk. The other thirty are “in the room” for reasons no one knows. They’re witnesses? Audience? No… maybe they’re alibis?! Calendar blocks required. Brain? Optional.
“We need to socialize this.” Let me Google Translate that one for ya: the decision cannot be made based on its merits. It must be pre-sold through a sequence of one-on-ones and small-group previews so that by the time the “decision meeting” happens, the decision is already fait accompli and the meeting is kabuki theater. If socialization is the national sport of your company…
The meeting after the meeting. The real conversation happens in the hallway, in the Slack DM, in the “quick sync” between the two people who actually have authority. The official meeting was the stage play. The meeting after the meeting is where the script gets written. There’s a particularly pernicious version of this, where 40 people do slide rodeo, then 32 leave, leaving the 8, who ostensibly have decision making power, but will definitely kick the can down the road. Tune in next week, we’ll do it all over again.
“Who decided this?” No one. Everyone. It remains unclear. The meeting as a tool for obfuscating accountability. You cannot point to a person, a document, or a moment where the choice was made. The decision emerged from the fog, fully formed, owned by no one. This is not an accident. This is strategic diffusion. This is CYA as organizational design. When the decision blows up, there’s no one to blame.
If you recognized three or more of these, my condolences. Your organization has substituted ritual for reasoning. The disease is advanced. Prognosis: not good.
Alignment: The Organizational Counterfeit
I fucking hate the word “alignment.”
At BigCo, it was a cancer. Everything was about alignment. Getting aligned. Staying aligned. Alignment meetings. Alignment decks. Check-ins to ensure continued alignment.
Here’s what alignment actually means: the organizational counterfeit of agreement.
Agreement requires: explicit positions, documented reasoning, acknowledged tradeoffs, someone’s name on the decision.
Alignment requires: bodies in a room, heads nodding at approximately the same time, no written record of who took what position.
Agreement can be audited and alignment can’t.
Alignment on the other hand, is a political act:
“I will neither agree nor disagree. I will wait until a later date, when I might launch spears at you. Or not. We’ll see.”
Alignment is the preservation of optionality. It’s strategic non-commitment dressed up as teamwork. You’re not saying yes. You’re not saying no. You’re saying I reserve the right to claim I was never really on board if this goes sideways, while also taking credit if it succeeds.
The aligned executive can pivot in either direction depending on how things unfold. Project succeeds? “I was a big fan from the start.” Project fails? “I had concerns that weren’t fully addressed.” The meeting provides no record of which.
When the decision goes sideways six months later, agreement is incontrovertible. “Here’s the memo. Here’s the counterargument. Here’s who decided and why.” Accountability! Voila!
Alignment has nothing. “We were all aligned.” Who decided? “We did.” Based on what argument? “We discussed it.” What were the dissenting views? Who knows.
The meeting is the Winston Wolf from Pulp Fiction: crime scene cleaner. Whatever reasoning happened (or didn’t) gets wiped. What remains is the social fact that people were present. That’s it.
Worse yet, here’s the trap: you can’t dissent from alignment without being difficult.
The person who writes “I disagree with this direction and here’s why” in a memo is doing their job. They’re creating a record. They’re offering a competing analysis. That’s how institutions are supposed to work.
The person who raises their hand in an alignment meeting and says “This doesn’t make sense to me,” is not a team player. They’re breaking the ritual. They’re making the room uncomfortable. They’ll be coached about their “collaboration style.”
Alignment optimizes for zero recorded disagreement. That’s omertà.
Debate: The Lost Art
To clarify: I’m not against people being in rooms together. I’m not against synchronous conversation. I’m against meetings.
Debate is different. Debate is an elegant weapon from a more civilized age.
A debate has explicit positions. Someone argues X. Someone else argues not-X. The positions are stated clearly enough that they can clash. Contrast that with a meeting, which has “perspectives” and “input” that somehow never directly contradict each other, just sort of… coexist in a quantum probabilistic fog of ur-agreement.
A debate has stakes. One position wins, or the positions synthesize into something neither party started with, or the participants agree on what they still disagree about. Something resolves. A meeting ends when the calendar says it ends. Nothing needs to be resolved. “Let’s continue this offline” is a valid (and popular!) meeting outcome. It is not a valid debate outcome.
A debate creates a record by its nature. The arguments are the record. “You claimed X because of Y. I disputed Y on grounds Z.” The clash itself is documentation. A meeting creates no record except “we met.” The positions taken, the arguments made, the counterarguments ignored… all of it evaporates when the room empties.
A debate requires commitment. You have to say what you actually think, out loud, in a form that can be challenged. Then, you have to defend it. You might be wrong, publicly. A meeting requires only presence. You can nod through the whole thing and never commit to anything.
I am a huge fan of debate. In person. On Zoom. In the hallway. In the comment sidebar of a shared document, where your objection sits there in black and white and the author has to either address it or visibly ignore it.
That last one matters. A document with vigorous comments is a debate. It’s asynchronous. It’s written. It’s preserved. And it forces engagement with opposing views in a way that meetings never do. The comment sits there, waiting. You have to respond.
Debate is cognitive conflict in service of truth-seeking. The clash is the point. Iron sharpens iron. You learn something, or you defend your position well enough that it deserves to survive, or you change your mind because someone made a better argument. Imagine that! Learning something!
Meetings are adversarial too? Sorta? But in service of positioning. The clash is covert. The weapons are covert: tone, timing, who speaks after whom, which concerns get “noted” and which get addressed. It’s politics masquerading as collaboration.
Debate is a black art now, passed from all memory like the One Ring. Most people in most organizations have never experienced it. They’ve experienced meetings where people disagreed, sure. But disagreement is not debate. Debate has structure. Debate has resolution. Debate has consequences.
Bring back debate. Kill meetings. They ain’t the same thing.
The Historical Collapse
How did we get here? This didn’t happen by accident. Three forces broke the memo (and debate) regime.
Speed compression. Globalization, deregulation, and financialization shortened decision cycles. Quarterly earnings pressure made multi-week memo review feel intolerable. Writing is slow. Reading carefully is slower. Meetings feel fast (even when they aren’t).
Managerial ideology shift. The rise of “professional management” culture reframed leadership as interactive rather than deliberative. Consultancies normalized alignment meetings, executive offsites, real-time consensus building. Written argumentation got quietly reframed as “academic” or “over-intellectualized.”
Communication technology paradox. Email and conferencing tools made synchronous interaction cheaper, but not more deliberate. Instead of enabling better writing, they lowered the cost of interruption, encouraged conversational decision-making, and penalized long-form thought.
Jack Welch’s GE was the canonical example: speed, informality, constant meetings valorized as virtues. Welch explicitly attacked bureaucracy, and the memo baby got tossed out with the bathwater.
Early stage Silicon Valley inherited a discussion-first culture from places like Xerox PARC, where innovation happened through whiteboards and hallway conversations. Lemming startups, in cargo cult fashion, have copied the surface behavior without the intellectual rigor underneath.
By the 1990s, the transformation was complete. Organizations stopped being machines of reason and became conversation machines.
The Modern Pathology
Today’s equilibrium is worse than meetings alone. Meetings replace memos. Slides replace arguments. Chat replaces follow-up. No durable decision record exists.
Organizations now run on: Calendar availability, narrative control, who was in the room.
This is why you see endless decision re-litigation. This is why no one, six months down the road, can point to why something was done. This is why institutional memory is, today, a sudoku puzzle grandma does.
The org chart says there’s a hierarchy, but the real currency is space on the calendar. If there is an explicit power structure, it’s: whoever controls the meeting cadence controls the organization.
From what I’ve witnessed, the people who thrive in this environment aren’t the best thinkers. They’re the best performers. The ones who can read a room, calibrate a take, land a sound bite, and dunk on someone without remorse (or understanding). The ones who see that alignment is a social achievement, not an intellectual one. Generally, these people seem to be narcissists of one stripe or another.
The thinkers (the ones who would have thrived in the memo era) either adapt, leave, or get ground down.
The Missing Configurator
In my essays on AI architecture, I keep returning to the Configurator problem. Yann LeCun’s JEPA framework proposes a module that sets parameters, decomposes tasks, and switches modes. But when asked how this Configurator actually learns, he punts: “I shall leave this question open for future investigation.”
The Configurator is the part that questions premises. The part that notices when the search space is wrong. The part that doesn’t just execute but asks “should we be doing this at all?”
In times past (the Cretaceous, apparently) the memo was the organizational Configurator.
It forced you to articulate assumptions before acting. It created a record that could be challenged. It made bad reasoning legible. It was the constraint system that kept institutional cognition vital and honest.
Without it, organizations do what transformers do: pattern-match against cached takes, execute confidently in the wrong direction, never notice that the premises were garbage.
The meeting is stimulus-response at organizational scale. The room convenes, reactions happen, outputs emerge, no one is quite sure how or why.
The Context Graph Delusion
It’s January 2026, and every enterprise AI pitch deck has the same white whale: capture the context graph.
The idea: all those meetings, Slacks, emails, Powerpoint decks on OneDrive, Sharepoint, wikis, Tableau queries, yada yada. There… we’ll find it there. They contain valuable “context” about how decisions were made. Small problem. This context is scattered, illegible, trapped in the heads of people who might leave. But wait, a solution! Use LLMs to capture, synthesize, and reconstruct the decision graph. Feed it the meeting transcripts. Feed it the Slack threads, git commit messages, Teams, Outlook, OneDrive! Let the AI surface the reasoning that led to Decision X.
This is presented as progress. It is actually a confession.
The context graph only needs “capturing” because you stopped creating it in the first place.
A memo is a context graph. It’s explicit. It says: “We decided X because of Y, despite concerns about Z, and we’ll revisit if W changes.” The reasoning is right there. It doesn’t need to be reconstructed by an AI forensics team sifting through collaboration data exhaust.
The “context” everyone wants to capture is the residue of illegible communication. It’s the ghost of the reasoning that would have existed if anyone had bothered to write it down. You’re not capturing context. You’re trying to reverse-engineer context from the scattered artifacts of its absence.
Here’s the thing: it won’t work.
The context in meetings is often strategically illegible. Remember alignment? “I will neither agree nor disagree, and reserve the right to launch spears later.” Remember the collective alibi? “Who decided this? No one. Everyone. It remains unclear.”
You cannot capture what was deliberately not committed. The fog is the feature. An AI that transcribes the fog just gives you a more detailed record of the fog. It doesn’t recover the reasoning, because the reasoning didn’t happen. Or it happened in the meeting-after-the-meeting, in the hallway, in the DM, in the places the transcript doesn’t reach.
The context graph fantasy is the organization saying: “We refuse to do the hard work of thinking clearly and writing it down. Instead, we’ll let AI reconstruct clarity from our confusion after the fact.”
News flash: clarity is not a post-processing step. Clarity is a discipline. It happens in the writing, or it doesn’t happen at all.
The cruelest part (or maybe it’s poetic?) is the organizations most desperate to “capture context” are the ones that have most thoroughly destroyed the practices that would create it. They’re actively hostile to memo culture, cuz they replaced debate with alignment. They let meetings metastasize into the entire operating system. “Help us, AI-wan, you’re our only hope.” Now they want the machine god to give them back what they threw away.
It won’t. You can’t reconstruct institutional memory from institutional amnesia. The context graph isn’t hidden in your Slack logs. It was never created.
The Context Graph startups are just trying to weaponize institutional apophenia.
Resist! Write the memo. Have the debate. Make the decision. Sign your name.
That’s your context graph. Everything else is cope.
Is There an Antibody?
Jeff Bezos famously banned PowerPoint at Amazon and required six-page narrative memos. Meetings begin with everyone reading the memo silently. Together, yes, but reading, not listening to someone perform.
This is widely cited as chef’s kiss. Yes, it’s better than Story Time for CXOs. But: notice what it concedes: the executives still won’t read the memo on their own time. They still require the synchronous ritual. Light the incense. The meeting is preserved; only its content has changed.
It’s a half-measure, like vaping, a harm-reduction strategy for organizations addicted to meetings. Better than nothing, but not a cure. An actual cure would be: decisions require written justification before the meeting. The meeting exists only to interrogate the document, not to consume it. Dissent is documented. The decision and its reasoning persist.
But this requires something most organizations have lost: the expectation that expensive adults will engage with written arguments asynchronously, and use their two brain cells simultaneously.
It requires understanding that thinking is expensive, and paying for it anyway.
A Valid Objection: Amazon’s Memo Dystopia
I can hear the objection forming: Amazon is also, by most accounts, a brutal place to work.
There was that New York Times exposé. Yep, there’s stack ranking and (shudder) “purposeful Darwinism.” There’s a churn rate that derives from treating humans as fungible inputs. Stories of people crying at their desks. Performance improvement plans are wielded like swords.
So what gives? If memo culture is the answer, why does the memo-culture company have a reputation for grinding people into slurry?
A few possibilities:
The memo is necessary but not sufficient. Written reasoning improves decision quality. It doesn’t automatically create psychological safety, humane management, or sustainable pace. You can have rigorous documents and a culture that treats people like shit. Amazon might be evidence that memos work for decisions while being orthogonal to whether the organization is good for humans.
In a low-trust, high-competition environment, the document can be weaponized. Your six-pager is a permanent record that can be used against you. “You wrote X in Q2. X was wrong. Explain yourself or die.” The memo culture that was supposed to enable honest reasoning instead enables forensic accountability. People don’t write to think; they write to defend.
Stack ranking poisons everything it touches. When your peers are also your competitors for a fixed number of “top performer” slots, every interaction is political. The memo doesn’t escape this. It becomes a performance, optimized for making you look smart relative to others rather than for collective clarity. The document is rigorous; the rigor serves career survival, not institutional cognition. (Hello, Moloch.)
Bezos was the Configurator. Maybe Amazon’s memo culture worked because Bezos himself was the forcing function. He read the memos. He interrogated them. He remembered what you wrote three years ago. The culture was “write well because Jeff will read it,” not “write well because writing clarifies thought.” When the forcing function is a single exceptional individual, you don’t have an institution; you have a court.
I don’t know which of these is most true. Probably all of them, in varying degrees.
But here’s what I take from it: the memo is not a sufficient condition for organizational sanity. It might be necessary. An organization that cannot produce written reasoning is definitely broken. But an organization that produces written reasoning in a climate of fear, competition, and disposability is broken in a different way.
The goal isn’t “memos.” The goal is institutional cognition, by which I mean the capacity for an organization to think, remember, learn, and correct itself over time. Memos are a tool that can serve that goal. They can also be perverted into weapons, performance objects, or bureaucratic theater.
To me, Amazon proves that memo culture has value. It doesn’t prove that memo culture is humane, or that the humans inside it thrive.
Maybe that’s the real lesson: you can have the constraint system and still be Moloch. The document forces rigor, but it doesn’t force kindness. The memo makes you think. It doesn’t make you good.
Wrapping This Long-Ass Essay Up
I know what I saw because I sat in the doggone rooms where the document existed and no one had read it, and where alignment judo-chopped agreement. I’ve been there when the meeting was the product and thinking was on vacation in Tahiti.
Story Time for CXOs. Execs with sippy cups. Somewhere, in an inbox no one opened, a well reasoned memo sat waiting patiently. Hoping, someday, an executive would adopt it and take it home. Sad story.
To recap: the feed paved your brain’s minimum-energy path. Meetings did the same move on the organization. Same wretched disease, same thermodynamics, same outcome. What remains is the performance of institutional cognition. A choreography of decision-making without the substrate that made decisions sensible.
Memo-destroying forces aren’t going away. If anything, they’ve gotten worse. Slack made interruption free, I don’t even have to find your cube anymore. Zoom made 8 back to back hours of meetings a reality. Something must be done.
Maybe the answer is small teams that write? Use the Bezos two-pizza rule, but focused on the memo? Keep the thinkers together. Let them use the constraint systems that have fallen into disfavor.
Maybe the answer is AI? I’m skeptical. But: as an eidetic institutional memory. “You decided X six months ago based on Y reasoning. That reasoning no longer holds. Do you want to revisit?” Maybe it’s a prosthetic for the organizational cognition we’ve lost.
Maybe there is no answer. Maybe meeting culture is a one-way ratchet. Maybe organizations, like individuals, can’t recover the capacity for deliberate thought once it’s been optimized away.
I can tell you this: if decisions can’t be traced to documents with names on them, you’ve abandoned institutional cognition and taken up “aligning”. And alignment is just omertà with expensive catering.
Colin Steele writes about cognition, coordination, and the thermodynamics of institutional degeneracy at colinsteele.org. He has sat through more Story Time sessions than he cares to count. He is not aligned.