Drawer 13 · 461 notes · 69 people · 2005–2026

Org design & culture

Team topologies, operating models, culture, and scaling organizations

Q:
Answers from Org design & culture notes, cited
Lenny’s Newsletter · Free post♥ 65

On taking time off

Apr 20, 2021 · 12 min

“Q: I’ve always wanted to take extended time off from work – a sabbatical – but have never mustered up the courage to do so. Is it a good idea? How do I get the most out of my time off, and what pitfalls should I avoid? I took a sabbatical while at Airbnb and it was one of the most transformative experiences of my life. I wouldn’t be doing this newsletter if not for that experience. I took three months off (after seven long years), and…”

SVPG · Marty CaganAug 21, 2008

Product Management Certification?

Aug 21, 2008 · 4 min

Marty Cagan argues that product management certification is premature and counterproductive for the software industry. He notes that the field is far from scientific, that software product success rates are poor, and…

Lenny’s Podcast78 min

How have I been complicit in creating the conditions I say I don’t want?

Jerry Colonna · May 8, 2025
Key learnings
  • Ask how you have been complicit, not responsible, in creating the conditions you say you don't want; this evokes personal agency…
  • Use radical self-inquiry to examine what you claim to want versus what you actually feel, such as saying you dislike busyness…
  • Notice whether your drive comes from proving your worth; separate the enjoyment of the work from the need to feel like somebody.
Lenny’s Podcast54 min

TiboSottiaux

TiboSottiaux
Key learnings
  • Expect most actions on the internet to be taken by agents, so build products that can serve agent traffic at scale and handle the…
  • Design for the capabilities you expect in roughly a year (about 10x better than today), not just what current models can do, to…
  • Favor systems that learn from your goals and feedback over hand-tuned agent loops and workflows, which Tibo thinks will be…
HEY World · Jason FriedJun 2, 2025

Turning back can be getting ahead

Jun 2, 2025

Jason Fried argues that when we meet a simpler system, idea, or implementation, our instinct is often to dismiss it as insufficient. He suggests a better response is to ask why our own work has become so complicated and…

SVPG · Marty CaganMar 21, 2023

Disruptive Technologies

Mar 21, 2023 · 4 min

Marty Cagan argues that the rapid rise of generative AI tools like ChatGPT, Midjourney and GPT-4 is a disruptive technology wave comparable to personal computers, the Internet, and the iPhone. He notes that disruptions…

SVPG · Marty CaganMay 6, 2010

The Office Of Silicon Valley

May 6, 2010 · 4 min

Marty Cagan describes a shared workspace he helped create in Silicon Valley for very early-stage startups, which often struggle with the time and money needed to set up an office. The space offers flexible…

Lenny’s Newsletter♥ 187

New data on the product job market

Jul 23, 2024 · 8 min
Subscriber post — summary only

Lenny Rachitsky shares near-real-time U.S. job-market data on product and product-adjacent roles, gathered via a third-party data firm. The post argues that growth roles are expanding fastest, PM hiring has plateaued…

SVPG · Marty CaganMar 14, 2005

Platform Product Management

Mar 14, 2005 · 3 min

Marty Cagan argues that platform product management, which means building foundation software that other companies use to create end-user solutions, is among the hardest and highest-leverage jobs in product. He first…

Lenny’s Podcast96 min

How to build deeper, more robust relationships

Carole Robin · Apr 25, 2024
Key learnings
  • Relationships sit on a continuum from contact-without-connection to functional, robust, and exceptional; you can build the skills…
  • Practice progressive disclosure using the 15% rule: step slightly outside your comfort zone, observe the response, then gradually…
  • Share appropriate vulnerability, such as admitting uncertainty or mistakes, rather than either oversharing or hiding everything…
SVPG · Marty CaganMar 19, 2022

Coaching vs. Mentoring

Mar 19, 2022 · 3 min

Marty Cagan distinguishes coaching from mentoring using a distinction he learned from Bill Campbell. Both are valuable, but mentoring is offered as honest opinion the mentee may or may not act on, so the mentor carries…

produxlabs.com · Melissa PerriJul 13, 2020

Onboarding in the Age of COVID-19

Jul 13, 2020 · 7 min

The author, who onboarded fully remotely at Produx Labs during the COVID-19 pandemic, argues that starting a job virtually is daunting but has real upsides. Remote hiring signals the company values the role, offers…

SVPG · Marty CaganAug 30, 2006

Usability vs. Aesthetics

Aug 30, 2006 · 3 min

Cagan argues that most websites are hard to use, ugly, or both, and that even companies that invest in design often fall short. He observes that interaction designers tend to produce usable but dull sites, while visual…

Lenny’s Podcast66 min

The role of AI in product development

Ryan J. Salva · Sep 4, 2022
Key learnings
  • Ring-fence a dedicated R&D team for long-horizon, uncertain bets, reserving roughly 5-10% of capacity for audacious experiments…
  • Hand off research prototypes only after customer signal exists, and move researchers back to R&D based on a trained replacement…
  • Let the team that owns the product day to day control its own roadmap; don't outsource innovation entirely to an R&D group.
Lenny’s Podcast91 min

Inside OpenAI

Logan Kilpatrick · Feb 8, 2024
Key learnings
  • Products built on general-purpose AI should either be radically better than ChatGPT in specific ways or focus on a narrow…
  • Give models rich context about who you are, your goals, and your audience; Logan argues context is the main lever for getting…
  • Treat prompt engineering like briefing a capable human with no background: explain the situation, the audience, and what good…
Lenny’s Newsletter♥ 13

One team, one roadmap - Issue 30

Jun 16, 2020 · 3 min
Subscriber post — summary only

Lenny answers a reader's question about having separate design and engineering roadmaps, arguing that cross-functional teams should converge on one source-of-truth roadmap. He outlines the core benefits of a shared…