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The Ask

124 points by digitallogic

by redelbee

7 subcomments

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?

by w10-1

0 subcomment

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.

by LeftHandPath

0 subcomment

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.

by TomMasz

0 subcomment

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.

by singingtoday

9 subcomments

Something about this writing feels off, but for the life of me I can't say exactly what.

by JSR_FDED

4 subcomments

This is either very profound or not at all. Can’t figure out which.

by 1123581321

0 subcomment

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.

by cik

0 subcomment

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.

0 subcomment

by nottorp

0 subcomment

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"?

by jdw64

0 subcomment

How did you start freelancing? -> The Ask: I want to become a Korea-based freelancer securing work from the US

by gjvc

3 subcomments

QUESTION / REQUEST / REQUIREMENT -- all nouns.
Not "Ask". "Ask" is a verb.

by sarabande

1 subcomments

This is extremely difficult to read. Can someone summarize the point?

by corndoge

0 subcomment

Seems like a good use of time

by subygan

3 subcomments

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?

by terabytest

0 subcomment

The atrocious writing style makes it at least obvious this wasn’t written by AI. Silver linings.

by clueless

0 subcomment

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

by danjl

4 subcomments

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.