Reading up on management
20 deep · digging since nov 19, 25
- John Cleese on Creativity in Management [video]
John Cleese argues that creativity requires a calm, playful, and open mental state, which management cultures often suppress through urgency and interruption.
- Sabotaging projects by overthinking, scope creep, and structural diffing
Overthinking, scope creep, and structural diffing sabotage projects by encouraging endless research and perfectionism instead of shipping.
- Should I Dress Like My Younger Co-Workers? - The New York Times
A fashion critic suggests older workers should resist pressure to mimic younger colleagues' attire, emphasizing personal style over conformity.
- AddyOsmani.com - Bias Toward Action
Bias toward action means taking the smallest responsible step with guardrails, using reversible decisions, error budgets, and safety nets to learn faster without catastrophic failure.
- AI Doesn’t Reduce Work—It Intensifies It
New research shows AI tools consistently intensify work by increasing pace, scope, and hours, leading to cognitive fatigue and burnout despite initial productivity gains.
- How I estimate work
Software estimates are political negotiations where engineers should treat them as time ranges that match management expectations, not accuracy exercises.
- No management needed: anti-patterns in early-stage engineering teams
Early-stage engineering teams often fail when they adopt corporate rituals like rigid standups and recurring 1:1s, which demotivate engineers and slow progress.
- Why Senior Engineers Let Bad Projects Fail - Lalit Maganti
Senior engineers let bad projects fail because being right and being effective differ; they strategically spend influence only when it matters.
- The Boss Who Hates Sick Day Requests - The New York Times
A boss's aversion to sick day requests highlights workplace tensions and the impossible demands placed on middle managers.
- I'm a Tech Lead, and nobody listens to me. What should I do?
A tech lead who feels unheard should build influence through visible impact and trust rather than relying on hierarchical authority.
- Most technical problems are people problems
Hacker News commenters debate how technical debt and system failures often stem from human factors like communication, politics, and organizational silos.
- Why Your CTO Might Start Coding Again - by Dave Griffith
As AI makes code generation cheap, former development managers—skilled in orchestration, review, and business judgment—are becoming more valuable as developers than specialists who only wrote code.
- Estimates – a necessary evil? - Erik Thorsell
Estimates become harmful when treated as deadlines rather than tentative guides, creating tension between developers and product owners.
- Transparent leadership beats servant leadership
The HN commenters largely argue that the author's 'transparent leadership' is just a rebranding of true servant leadership, which already includes teaching and empowerment.
- How to Attend Meetings
HN commenters largely agree with slide-deck advice on declining useless meetings but cite cultural resistance and lack of enforcement as barriers.
- Seeing like a software company
Large software companies sacrifice efficiency for legibility to control scale and enable enterprise deals, despite slowing engineering velocity.
- The Math of Why You Can't Focus at Work
Interruption rate, recovery time, and minimum focus block size mathematically determine whether a workday yields deep work, with simulations showing small parameter changes drastically shift productivity.
- Feedback doesn't scale
As organizations grow beyond 100 people, feedback becomes overwhelming noise because personal relationships don't scale, requiring structured systems like proxy relationships and working groups to replace direct trust.
- What Good Execution Looks Like - Yusuf Aytas
Good execution is defined by quiet, low-noise operations where clear direction, stable context, clear ownership, and trust enable teams to deliver without friction or management theater.