The Ask (randsinrepose.com)
123 points by digitallogic 3 days ago
redelbee 6 hours ago
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?
jmole an hour ago
The $5 trillion didn't come from nowhere. People spend money on the products because they are helpful.
However, you're right that most people at these companies are so accustomed to the "free money faucet" from ads, huge margins, etc. that it's incredibly easy to end up totally disconnected from reality. That's probably what frustrates you the most.
I will say - after having left Google just about a year ago now - that there is literally no better time to make money in tech than right now. AI is eroding the moat of all large tech companies, and skilled individuals with passion and drive can make a huge impact on the world with an incredibly small budget.
You'll make it. All of us will.
allknowingfrog 34 minutes ago
I think "because they are helpful" is OP's point of contention. Tobacco isn't helpful, but it's a product that people spend money on.
throwway120385 2 hours ago
We flipped from an Epicurean mindset to a Stoic or Nihilistic mindset. IOW, we stopped talking about helping people lead good lives and started talking about how we can all weather stress and work hard and deprive ourselves of good things to build something. Or we're talking about how nothing matters so why bother?
cush an hour ago
Sounds like you’re really going through it. Sorry to hear
keybored an hour ago
Some people long for a savior-leader to come along and right the ship. An Obama that can from the top make all the stuff underneath right. They can’t do it themselves because structurally they, the middle or lower layer, are deadlocked, or the system makes things unsurmountable. But then it turns out that the savior-leader can’t make things right because they too are a product of the system. Just as convinced that the system is too broken for them to fix.
SpicyLemonZest 2 hours ago
There's an intuitive appeal in having a coordination mechanism where good leaders decide which problems are important to work on and then get the smart people to work on those problems. But historically, societies structured that way haven't worked well; they struggle to get good signals on whether the solutions make sense, and the coordination mechanisms are vulnerable to subversion by bad leaders. The Soviet Union famously forbade anyone from researching genetics for decades because a crank named Trofim Lysenko who didn't think it was real happened to become politically popular.
jon-wood an hour ago
There is probably a middle ground somewhere between literal Soviet communism and unregulated capitalism. There are quite a lot of countries happily functioning in that middle ground, and while they're not making 15 people incredibly wealthy they're also not grinding the rest of the population into the ground.
SpicyLemonZest an hour ago
dnnddidiej 5 hours ago
You need socialism. That is not a snark. I am serious. It is getting rarer in the world. Even the "left" is very capitalist.
w10-1 9 hours ago
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.
TomMasz 30 minutes ago
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.
LeftHandPath 4 hours ago
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.
singingtoday 10 hours ago
Something about this writing feels off, but for the life of me I can't say exactly what.
allknowingfrog 22 minutes ago
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.
Cthulhu_ 9 hours ago
It's the writing of someone who has been writing articles like this for decades now, instead of your average blogger or journalist. Just enjoy the difference.
gradstudent 7 hours ago
Can confirm! I've been reading Rands for 20 years now
Cthulhu_ 7 hours ago
joenot443 39 minutes ago
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.
ikari_pl 9 hours ago
To me, as a non-native speaker it feels like a series of interruptions and focus changes with no natural flow. Hard to follow.
andyjohnson0 7 hours ago
This is just how he writes. Busy-executive-bullet-point style. Its not AI.
drcongo an hour ago
It's that opening paragraph.
> Coffee in hand, I sit down in the Cave. Any Tuesday during the work week, a sip, and I parse the calendar.
How many Tuesdays are there in his work week?
ForHackernews 8 hours ago
Terminal LinkedIn brain
sdevonoes 9 hours ago
Very. Short. Sentences. That’s AI
Cthulhu_ 7 hours ago
AI is trained on but more importantly prompted to write in that style. It's not just annoying⸻it's a choice.
chrisweekly 2 hours ago
Wrong. Look at the author's long history of posts.
whowasmark 9 hours ago
Look up the organizational chart meme. Look at Amazon's chart. You'll know what's off.
JSR_FDED 15 hours ago
This is either very profound or not at all. Can’t figure out which.
leokennis 7 hours ago
Apart from the tone which is not my cup of tea either, I think what these types of articles/advice try to convey is that we (the working population) are still the monkeys we were thousands of years ago.
Sometimes we do stuff well because we like the other monkey we're doing it with. Sometimes we do stuff badly because we are an angry monkey. Sometimes we do the right thing but we cannot really explain why. We can sort of predict what the future will be like but not really well.
Management is pretending to "execute programs" and "align value chains" and "strategize on market trends" because the suits they wear are very expensive. But the reality is that they are also monkeys, who try to manage the emotions and urges and pitfalls of other monkeys by guiding interactions between the monkeys.
This kind of slightly wooly, slightly look-at-me-being-business-y kind of writing feels to me like selling your "I'm a monkey who can sometimes make other monkeys interact more effectively" as some cold hard logical skill.
Hugsbox 22 minutes ago
Just felt like a pointless LinkedIn post, I don't understand what everybody else sees in this article.
jaggederest 15 hours ago
I think much of this kind of management faffery might be like advertising - I know half is useless, but I'll be damned if I can figure out which half.
SoftTalker 13 hours ago
Half useless, half unnecessary.
whowasmark 9 hours ago
We never found out who Mark was. Or what the problem with Rachel was. Or what and why behind and ahead of the pressure to meet either were in place. So going with not at all. They've literally described their job as having too much cruft that could have been partially solved by the non-existence of their role.
aswegs8 7 hours ago
Well at least it led to you finally creating an account on HN. Welcome!
randallsquared 4 hours ago
If they aren't doing this role, then each of the 10 people they directly manage will end up doing 20% of it, and there will be another 30% that no one does and causes large but untraceable-to-this-absence issues in a year.
1123581321 14 hours ago
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.
cik 11 hours ago
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.
Both matter. I appreciate this reminder.
nottorp 4 hours ago
Interesting reaction to Rands' style.
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"?
jdw64 13 hours ago
How did you start freelancing? -> The Ask: I want to become a Korea-based freelancer securing work from the US
gjvc 6 hours ago
QUESTION / REQUEST / REQUIREMENT -- all nouns.
Not "Ask". "Ask" is a verb.
jeremyjh 6 hours ago
"The Ask" is in widespread usage as a noun.
gjvc an hour ago
that does not in any way make it correct
greekrich92 5 hours ago
The nouning of verbs is a very annoying type of corpo speak
throw0101c 3 hours ago
“Verbing weirds language.” — Bill Watterson, Calvin and Hobbes, https://www.gocomics.com/calvinandhobbes/1993/01/25
aswegs8 6 hours ago
Ask is a noun
sarabande 8 hours ago
This is extremely difficult to read. Can someone summarize the point?
aswegs8 6 hours ago
I had the same instinct. Was about to copy paste it into ChatGPT to summarize. But powered through it. tl;dr: your job as a senior manager is to listen to people
corndoge 11 hours ago
Seems like a good use of time
subygan 14 hours ago
I hate middle management as much as the next guy.
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?
jimbokun 12 hours ago
Relationship oriented workers keep their network as they move from job to job. Never know who you might be able to help or be helped by in the future.
chipsrafferty 11 hours ago
Well, nobody said lifers. But you can't really get a management job without already having management experience. You typically have to be promoted internally, not just go look for a management job elsewhere with no experience.
busterarm 13 hours ago
I'm in a big org and while we had a lot of COVID-related turnover, before and after COVID our average engineer tenure went from ~1.6 years to something like 6-7. I'm at the upper end of my part of the org at 8+ (one at 9, one at 11 one at 13). Only like 3 people in my group are below 6.
I would like to move on but also given the current climate that seems ludicrous.
People I talk to in similar places are in the same boat. Hiring is frozen, there's not enough people to manage everything we have, and everyone remaining is hanging on for dear life.
terabytest 9 hours ago
The atrocious writing style makes it at least obvious this wasn’t written by AI. Silver linings.
clueless 3 hours ago
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
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
danjl 14 hours ago
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.
andrewmutz 13 hours ago
I don't agree with this.
But I also found the article really unsatisfying. The idea that middle management should spend enormous amounts of time building relationships because other middle managers got vibes that one day it might be useful is insane. I think the article represents the worst of big, slow tech bureaucracies.
Replacing middle management with AI would not work, but using AI to avoid managers needing to have all these meetings would probably work really well. The idea that there's some AI system that has access to all the documents/email/task management systems at the company is a good one, and it could identify situations (like the one in the article) where two projects on opposite ends of the organization are colliding.
Instead of two middle managers needing to do 1:1s with no clear need for years because other middle managers got vibes that they should could be replaced by an AI system that uncovered situations like the ones mentioned in the article.
This wouldnt replace middle managers, but it might help them do their jobs better.
fallous 13 hours ago
Adding AI to an organization that is somehow making process decisions based on "vibes" isn't going to solve problems, it's simply going to add yet another problem generator to a dysfunctional system.
danjl 13 hours ago
I mostly agree. I'm curious to hear more details about why you think AI cannot replace middle management?
busterarm 11 hours ago
> The idea that middle management should spend enormous amounts of time building relationships because other middle managers got vibes that one day it might be useful is insane. I think the article represents the worst of big, slow tech bureaucracies.
If your org has anywhere north of 100 engineers across separate teams, intelligence gathering and relationship/trust-building is the only way to effectively do work that crosses the boundary of your team's area of responsibility. It's also the only way to protect your team from stepping headfirst into hot bullshit cooked up by clueless product managers, junior executives and other engineering teams who've unilaterally decided your area of responsibility is in their critical path.
> Instead of two middle managers needing to do 1:1s with no clear need for years because other middle managers got vibes
This isn't actually how this happens in practice. These 1:1s happen after their teams consistently have to share ownership over something or their work conflicts. It's more of a standup saying what your team is doing and what you're concerned about than a typical 1:1. You also calibrate the frequency as needed. For most of these it's a QBR but for some teams this will be monthly or even weekly. It's not "because vibes".
simonw 12 hours ago
A key job of management is to figure out what's actually going on, as opposed to just what people tell you is going on.
LLMs are inherently gullible.
roenxi 8 hours ago
Human managers are inherently gullible; we've got no plausible path to unbias them. LLMs have at least one plausible path which is to train them to be a little bit cynical.
We're not going to call it "management" necessarily, but there is no question that LLMs are going to take over decision making from managers eventually. Why choose a monkey guessing what the evidence says you should do when you could have an optimised evidence-weighted statistical model making the bets? The only reason to use humans is there are still technical limits on how general the models are, limits that seem to be falling away at a pleasing rate.
ben_w 4 hours ago
motoxpro 4 hours ago
diatone 3 hours ago
2b3a51 7 hours ago
passive 13 hours ago
Firm, but partial, disagreement.
People, especially in remote jobs, benefit from being organized into groups intentionally, with distinct rituals that enable them to operate effectively while they get to know each other better. Another person needs to design and oversee all that.
While you can provide templates for that structure that allow oversight to scale so that one person can oversee larger groups, that tends to be more effective in non-remote, and more predictable, work environments. Modern software development is very little of that.
I don't have much in-person experience with middle management in contexts outside of software development, and I suspect there are some opportunities to use AI to bring engineers closer to customers.
nottorp 4 hours ago
> with distinct rituals
If you do rituals you'll get ritual compliance, not people getting to know each other better.
DonHopkins 7 hours ago
AI Orchestrated Waffle Parties
cweagans 14 hours ago
I have a theory. How close does the following describe you?
* You're an engineer with 3-6 years of experience in a primarily IC role
* Maybe you've done some tech lead stuff, but you've never actively worked in engineering management.
* You feel that management (and HR for some reason?) is constantly in the way of you getting stuff done, and that your life would be easier if you could simply decline every meeting and only communicate through pull requests.
Humor me, please. I'll explain after.
atherton94027 12 hours ago
Middle-management as we knew it at the turn of the 2010s is probably gone forever. You don't need to coordinate many many teams as you used to. Same as huge frontend team with dedicated support for graphql, etc. AI made most of that redundant.
By extension we're going to need a lot less middle managers as coordination problems decrease.
As for the point I think you're trying to make, the problem with middle management and other chokepoints in general (like PM teams) is that often they become an antipattern. They soak in all the information and then dole it out parsimoniously, so the typical experience as an IC is to be barely able to see the full picture
LPisGood 13 hours ago
For the sake of moving this along, that describes me perfectly. Please, continue.
motoxpro 4 hours ago
danjl 13 hours ago
I have 35+ years experience as a manager and engineer at large enterprise tech companies (what the kids now call FAANG, though some of the company names were different back then), and was a Founder, CEO and CTO at a $7M VC funded company and several other "differently-funded" startups.
cweagans 12 hours ago
jimbokun 12 hours ago
busterarm 13 hours ago
Couple decades in with some leading but still remaining an IC officially.
The right work just doesn't get done without staff engineers and architect types having frequent conversations & meetings as well as constant code reviewing. Or long-term ICs effectively doing this role without the title and expectations/responsibilities (raises hand). You can identify these people because they ask questions relentlessly. Always well-considered ones, but even the ones that might make them look stupid in a meeting.
Coding is a small percentage of the work but also just as important. That's the sweet spot. The "non-stop meetings/socializing" people and the "headphones on & grind PRs" types are both two extremes of behavior that are boat-anchors in any organization and will bring productivity/customer-impact to a screeching halt if it goes unchecked for long enough.
And it's _always_ those stupid-seeming questions that uncover showstopping problems that would have bit you if left ignored.
Edit: Not to greenlight anything Palantir is doing, but in my opinion the FDE/FDSE model is probably everyone's near-future if your company is B2B. You can't be an "ignore meetings" type of person and do that.
qsxfthnkp2322 13 hours ago
It’s a trap.