but in this case, specifically. who are these career people thinking about orgs and their movement in years?
especially in a job economy where employees are expected to be laid off despite "staggering profits". It feels completely orthogonal to the environment I exist in.
is there room for lifers in big orgs? without getting the boot or worrying about the boot?
I liked this, although it seemed like there were unusual typos/missing words for Rands in a couple of places. Is this a book draft?
It's a good exercise to mentally go around the a meeting room and think about what each person wants from it. Given Rands' job, he obviously starts thinking about it earlier, and for longer, but even a few minutes while everyone's settling in and chit-chatting can make a difference in how you participate.
Harsh take: AI should replace most middle management. It is the easiest part of an organization to replace. The people making things should mostly communicate about company strategy, cross-team issues, and job requirements with an AI. There should be a handful of high-level strategy on top of the AI. The AI should have access to all the documents for the company. The middle management should be put in a spaceship along with HR and sent off to another planet so the people who build things can just get stuff done. This will never happen.
I've been enjoying Rands for what feels like 2 decades now. Spot on, over and over again. Great advice few newbies, great reminders for people who have been there before - just generally great.
I take this as generally focusing on the what ask (and hence give) becomes. But it reminds me of the business classic Theory of Constraints. To me the laserlike focus, or attempt to get to singular clarity is the point; in this highlight we're seeing the notion of software skills rather then a data-based approach, as it's a soft problem.
I think it's just a characteristic voice. Just like you can tell Vonnegut, DFW, or Palahniuk from a couple paragraphs, Rands developed a pretty distinct sound.
It's awfully literary. It reads like James Joyce attempting to convey advice about effective leadership for technical teams. In my opinion, it's an obnoxious, pretentious approach to writing about practical subjects, but I may be in the minority.
For a senior manager, the main problem is organizational blinders: people not seeing the direct route (through fear, ambition, loyalty, etc.) Senior people get to ask the cross-cutting questions that others can't (and let the chips fall).
For line managers, they are deluged with impossible, specific asks and they have no real way of knowing if the team will be able to perform, or be happy to. They survive by maintaining fictions and blinders, and staying just ahead in chips.
I think he's underselling to say it's instinct; in law it's called ripeness, waiting for when something really needs to be addressed, and then ideally just reflect that in a way people can take on instead of taking control. The senior's job is not to intervene unless necessary, and even then to prefer activating others.
So I feel it's a project manager mindset to always be tallying asks; while a senior manager is really tracking issues and capabilities on a different timescale, doing the prep to build the capability to address the issue when it's ripe.
I understand the following isn’t the point of this piece and yet I still can’t help wondering: How much better off we would all be if “senior management” stopped playing these games to get things done and instead spent most of that time really considering the things getting done and whether they are ultimately good for individuals and society at large. We don’t need another product from the “fruit company” and we certainly don’t need most of what our collective work is making today.
Don’t get me wrong, I absolutely love and crave the experience of working with other people to make things. And I cannot for the life of me understand why seemingly intelligent and talented people like Rands would fritter away their lives and those of others in such trivial pursuits in many cases, and downright evil doings in others.
Here I am, worrying about how I am going to afford housing after a divorce, and I’m reading insightful leadership advice from an author who has seemingly spent their career building this leadership expertise at one company that makes the most insanely technologically advanced gambling distraction devices imaginable, another company that makes war and mass surveillance products seemingly out of a corporate strategy to profit from human suffering, and the least objectionable company that only made the most distracting communication-platform-cum-torture-device when it convinced us all email wasn’t fast enough to get things done™ and that now embodies an actual AI hallucination as a company strategy. Why can we not have good leaders in making a society where divorce doesn’t threaten basic human needs? Or maybe one where healthcare is a given? Food being widely available?
Instead we band together and create more than $5 trillion worth of “value” in three companies that make absolutely nothing of worth to real human needs. And then we read about the games played inside those companies by humans who could be using their skills for anything else useful and we come here to argue about the merits of middle management.
What are we doing? How did we get here? Can any leadership help us work together to dismantle the horrors we’ve created to make room for making things that address real needs?
As someone who has been CTO at a small company, senior leadership at a scaleup, and now middle management at a large co, I can tell you that what you are imagining is not structurally possible in our current system.
That's not say leaders here and there aren't thinking about what they're building and the macro effects, but you have to understand that unless you're bootstrapped and self-funded, even the most morally minded CEO is still beholden to investors who primarily care about money. You can only be as ethical as your board allows, and that primarily comes from profitability and financial success. In the good times its easy to talk a big game (eg. Google's "Don't be Evil"), but eventually competition comes for us all, and if your morality is hurting the bottom line you will be replaced. The backstop would be customer sentiment, but most buyers (whether B2B or B2C) are also not morally motivated. That's why free + ads is the dominant model, why micro payments failed despite years of techie hand-wringing, and paid consumer apps outside of streaming are vanishingly rare.
It's not all hopeless though. If things reach a high enough threshold of public sentiment then we can put legal and cultural pressure that will actually change things top-down. I think this is where AI is probably going as it's the most universally feared and hated impact across party lines that I have seen during my life, and the leaders in charge seem incredibly tone deaf about how it's being perceived, so I do expect regulation and softer forms of social enforcement to affect that trajectory. But if you're hoping for individual CEOs and leaders to fix our systemic problems, don't hold you're breath, they are just as replaceable as the workers under them.
cos people will do things for money. Regulate money, tax better, redistribute better. Give more people the power to say "no" as opposed to "holy fuck I need to make rent next month".
Politically addressing needs has the same issue as regulating money, its unpopular either because of billionaire marketing or general ignorance and cognitive dissonance. Also resource allocation is hard when people interpret any level of cut as murder. So you're hemmed in on both sides while FPTP makes it impossible to be honest with the electorate where jetpacks for everyone and free head is what wins you elections, regardless of its delivery.
While some commenters might suggest socialism is the panacea, I think that's just a different format of the same sort of failure. The fundamental flaw in our societies is ourselves, as we build societies that reflect our own failures. We care for ourselves considerably more than we do others, sometimes aggressively against others, sometimes will utter, wilful ignorance of others. The big picture is too hard for our brains to deal with. We have no baseline emotional regulation, humans can wrap themselves into the same emotional state about leaving Britney alone as they do about the death of a loved one. This means everyone's needs seem the same, which makes resource allocation hard.
We see a similar whine about immigration where the abstract is simply: You get $10k and an immigrant moves next door, or you get $0k and an arbitrary person who isn't an immigrant moves in next door. Solve for the status quo. But people will elect governments on a policy of cruelty to think that status quo won't immediately rubber band back.
One of the rare articles that distills a lot of abstract experience into something clear and actionable. Reminds me of Spolsky's more famous blog posts on software engineering.
This is unrelated to this article, but I see such simple titles posted on HN often and given how many articles I read per day on HN, I don't know if it's worth me reading or not until I click it. I wish we had a feature on HN that semantically defined who the intended audience for an article is, specially for such opaque titles. Something like the following (used gemini for this):
Here are the 1-2 tags defining the intended audience for each article on the front page:
Five frontier LLMs disagree on 67% of 1k real-world fact-check claims
Tags: AI Researchers, Machine Learning Engineers
YouTube to automatically label AI-generated videos
Tags: Digital Content Creators, General Tech Consumers
A Eureka machine that thinks like nature and explores what AI cannot
Tags: Computer Scientists, AI Researchers
AMD pulls a bait-and-switch on Linux users with Vivado licensing changes
Tags: Linux Users, Hardware Engineers
I analysed 20 years of my chats
Tags: Data Enthusiasts, Hobbyist Programmers
I think Anthropic and OpenAI have found product-market fit
Tags: Tech Entrepreneurs, Product Managers
It's interesting to see things from a senior manager's viewpoint, especially in comparison to what I experienced as a mid-level manager. But it's funny to see that they also end up in meetings that seem to have no reason to happen. We all laugh at "this meeting could have been an email", yet we experience it on regular basis and that's just how things are done.
So, cynically, (and I say this with no disrespect intended to the author directly): a screed about how to continue justifying your existence as a—ostensibly "good"—middle manager (using, as its basis, one of the most nausea-inducing jargon terms to ever claw its way out the semi-sentient Dunning–Kruger ooze that is corporate-speak.)
And, to be clear, I do actually think a good middle manager is beneficial, if most commonly in the way of any necessary evil, as a very effective grease for the oft poorly meshing cogs of business. Not unlike the fresh breeze of an actually effective project manager or personable AND productive engineer.
I'm not a native English speaker, but have been reading and sometimes speaking English for decades. For me 'the ask' feels strange. It sounds like it's just a verb made into a noun, like saying 'the sing' or 'the eat'. "I had an eat" "Three asks".
What would make someone want to write 'the ask' and not 'request' or even just 'question'? How is it different?
There’s a common phrase in English: “what’s the ask?” As in, “what is the other party requesting?” “What does this person want?”
I can see how that would sound/read a bit strange to one coming from another culture. It’s just another way of stating the concept of the purpose behind the reason for a person’s request, actions, statement, or in this case, why they requested a meeting.
Getting to “the ask” here meant, for the author, “what the hell does this fool REALLY want out of me?”
I prefer Walt’s approach. When I was 19, I worked for a small business up in Colorado. They had this contractor named Walt that did all their email, website, all that stuff (very early 2000s). Every time he answered the phone, it wasn’t a polite “Hello?”, no! Walt got straight to the point with one loud, gruff word that immediately set the tone for all his conversations:
29 comments
[ 399 ms ] story [ 1093 ms ] threadbut in this case, specifically. who are these career people thinking about orgs and their movement in years?
especially in a job economy where employees are expected to be laid off despite "staggering profits". It feels completely orthogonal to the environment I exist in.
is there room for lifers in big orgs? without getting the boot or worrying about the boot?
It's a good exercise to mentally go around the a meeting room and think about what each person wants from it. Given Rands' job, he obviously starts thinking about it earlier, and for longer, but even a few minutes while everyone's settling in and chit-chatting can make a difference in how you participate.
I take this as generally focusing on the what ask (and hence give) becomes. But it reminds me of the business classic Theory of Constraints. To me the laserlike focus, or attempt to get to singular clarity is the point; in this highlight we're seeing the notion of software skills rather then a data-based approach, as it's a soft problem.
Both matter. I appreciate this reminder.
For line managers, they are deluged with impossible, specific asks and they have no real way of knowing if the team will be able to perform, or be happy to. They survive by maintaining fictions and blinders, and staying just ahead in chips.
I think he's underselling to say it's instinct; in law it's called ripeness, waiting for when something really needs to be addressed, and then ideally just reflect that in a way people can take on instead of taking control. The senior's job is not to intervene unless necessary, and even then to prefer activating others.
So I feel it's a project manager mindset to always be tallying asks; while a senior manager is really tracking issues and capabilities on a different timescale, doing the prep to build the capability to address the issue when it's ripe.
Not "Ask". "Ask" is a verb.
Don’t get me wrong, I absolutely love and crave the experience of working with other people to make things. And I cannot for the life of me understand why seemingly intelligent and talented people like Rands would fritter away their lives and those of others in such trivial pursuits in many cases, and downright evil doings in others.
Here I am, worrying about how I am going to afford housing after a divorce, and I’m reading insightful leadership advice from an author who has seemingly spent their career building this leadership expertise at one company that makes the most insanely technologically advanced gambling distraction devices imaginable, another company that makes war and mass surveillance products seemingly out of a corporate strategy to profit from human suffering, and the least objectionable company that only made the most distracting communication-platform-cum-torture-device when it convinced us all email wasn’t fast enough to get things done™ and that now embodies an actual AI hallucination as a company strategy. Why can we not have good leaders in making a society where divorce doesn’t threaten basic human needs? Or maybe one where healthcare is a given? Food being widely available?
Instead we band together and create more than $5 trillion worth of “value” in three companies that make absolutely nothing of worth to real human needs. And then we read about the games played inside those companies by humans who could be using their skills for anything else useful and we come here to argue about the merits of middle management.
What are we doing? How did we get here? Can any leadership help us work together to dismantle the horrors we’ve created to make room for making things that address real needs?
That's not say leaders here and there aren't thinking about what they're building and the macro effects, but you have to understand that unless you're bootstrapped and self-funded, even the most morally minded CEO is still beholden to investors who primarily care about money. You can only be as ethical as your board allows, and that primarily comes from profitability and financial success. In the good times its easy to talk a big game (eg. Google's "Don't be Evil"), but eventually competition comes for us all, and if your morality is hurting the bottom line you will be replaced. The backstop would be customer sentiment, but most buyers (whether B2B or B2C) are also not morally motivated. That's why free + ads is the dominant model, why micro payments failed despite years of techie hand-wringing, and paid consumer apps outside of streaming are vanishingly rare.
It's not all hopeless though. If things reach a high enough threshold of public sentiment then we can put legal and cultural pressure that will actually change things top-down. I think this is where AI is probably going as it's the most universally feared and hated impact across party lines that I have seen during my life, and the leaders in charge seem incredibly tone deaf about how it's being perceived, so I do expect regulation and softer forms of social enforcement to affect that trajectory. But if you're hoping for individual CEOs and leaders to fix our systemic problems, don't hold you're breath, they are just as replaceable as the workers under them.
Politically addressing needs has the same issue as regulating money, its unpopular either because of billionaire marketing or general ignorance and cognitive dissonance. Also resource allocation is hard when people interpret any level of cut as murder. So you're hemmed in on both sides while FPTP makes it impossible to be honest with the electorate where jetpacks for everyone and free head is what wins you elections, regardless of its delivery.
While some commenters might suggest socialism is the panacea, I think that's just a different format of the same sort of failure. The fundamental flaw in our societies is ourselves, as we build societies that reflect our own failures. We care for ourselves considerably more than we do others, sometimes aggressively against others, sometimes will utter, wilful ignorance of others. The big picture is too hard for our brains to deal with. We have no baseline emotional regulation, humans can wrap themselves into the same emotional state about leaving Britney alone as they do about the death of a loved one. This means everyone's needs seem the same, which makes resource allocation hard.
We see a similar whine about immigration where the abstract is simply: You get $10k and an immigrant moves next door, or you get $0k and an arbitrary person who isn't an immigrant moves in next door. Solve for the status quo. But people will elect governments on a policy of cruelty to think that status quo won't immediately rubber band back.
Does going throuh all that "AI" slop daily makes people unable to tolerate any other kind of style?
Is "it was AI generated" a replacement for "I don't like his style"?
Here are the 1-2 tags defining the intended audience for each article on the front page:
Five frontier LLMs disagree on 67% of 1k real-world fact-check claims Tags: AI Researchers, Machine Learning Engineers
YouTube to automatically label AI-generated videos Tags: Digital Content Creators, General Tech Consumers
A Eureka machine that thinks like nature and explores what AI cannot Tags: Computer Scientists, AI Researchers
AMD pulls a bait-and-switch on Linux users with Vivado licensing changes Tags: Linux Users, Hardware Engineers
I analysed 20 years of my chats Tags: Data Enthusiasts, Hobbyist Programmers
I think Anthropic and OpenAI have found product-market fit Tags: Tech Entrepreneurs, Product Managers
Hallucinate – Massively Multiplayer Online Rave Tags: Gamers, Creative Coders
AI sticker shock hits corporate America Tags: Corporate Executives, IT Managers
SimCity 3k in 4k (2025) Tags: Retro Gamers, Game Developers
Rapira (Рапира) – Soviet programming language interpreter Tags: Programming Historians, Language Enthusiasts
What Apple and Google are doing to push notifications Tags: Mobile Developers, Privacy Advocates
Commission fines Temu €200M for breaching the Digital Services Act Tags: E-commerce Professionals, Tech Policy Analysts
Ruby vs. Java vs. TypeScript: my experience on building a Cowork DOCX plugin Tags: Software Engineers, Web Developers
I'm Getting into Mesh Networks (Meshtastic, MeshCore, and Reticulum) Tags: Network Enthusiasts, Maker/DIY Community
More Whimsical OEIS Sequences Tags: Mathematicians, Recreational Math Enthusiasts
Libwce: The entropy layer of a wavelet codec, on its own Tags: Compression Engineers, Systems Programmers
The Ask (the article you previously asked about) Tags: Engineering Managers, Tech Leaders
Seeing Around Corners Using Smartphone-Grade Lidar Tags: Computer Vision Researchers, Optics Engineers
Rust (and Slint) on a Jailbroken Kindle Tags: Hardware Hackers, Rust Developers
DuckDuckGo search saw 28% more visits after Google said people love AI mode Tags: Search Engine Marketers, Privacy Advocates
Investigating how prompt politeness affects LLM accuracy (2025) Tags: AI Prompt Engineers, NLP Researchers
Go: Support for Generic Methods Tags: Go Developers, Systems Programmers
Biff is a command line datetime Swiss army knife Tags: System Administrators, CLI Power Users
FBI Arrests CIA Official with $40M in Gold Bars in His Home Tags: General Audience, Intelligence Buffs
RamAIn (YC W26) Is Hiring Tags: Job Seekers, AI Engineers
Warm up your MacBook (2019) Tags: Mac Users, Hardware Hobbyists
Incident with Pull Requests, Issues, Git Operations and API Requests (GitHub) Tags: DevOps Engineers, Software Developers
A New Typst Template for Pandoc (2025) Tags: Academic Writers, Technical Writers
Stress disrupts hippocampal integration of overlapping events, memory inference Tags: Neuroscientists, Psychology Researchers
Google employee charged with $1M Polymarket insider trading bet on search term Tags: Tech Finance Enthusiasts, General Tech Consumers
And, to be clear, I do actually think a good middle manager is beneficial, if most commonly in the way of any necessary evil, as a very effective grease for the oft poorly meshing cogs of business. Not unlike the fresh breeze of an actually effective project manager or personable AND productive engineer.
https://web.archive.org/web/20170918052437/http://www.jerkci... https://bonequest.com/715
https://web.archive.org/web/20170918052444/http://www.jerkci... https://bonequest.com/712
I'm not a native English speaker, but have been reading and sometimes speaking English for decades. For me 'the ask' feels strange. It sounds like it's just a verb made into a noun, like saying 'the sing' or 'the eat'. "I had an eat" "Three asks".
What would make someone want to write 'the ask' and not 'request' or even just 'question'? How is it different?
I can see how that would sound/read a bit strange to one coming from another culture. It’s just another way of stating the concept of the purpose behind the reason for a person’s request, actions, statement, or in this case, why they requested a meeting.
Getting to “the ask” here meant, for the author, “what the hell does this fool REALLY want out of me?”
I prefer Walt’s approach. When I was 19, I worked for a small business up in Colorado. They had this contractor named Walt that did all their email, website, all that stuff (very early 2000s). Every time he answered the phone, it wasn’t a polite “Hello?”, no! Walt got straight to the point with one loud, gruff word that immediately set the tone for all his conversations:
“WHAT?!”