Drawer 06 · 560 notes · 139 people · 2005–2026

Leadership & management

Managing people, feedback, coaching, and leading product teams

Q:
Answers from Leadership & management notes, cited
HEY World · Jason FriedFeb 21, 2025

Hiring judgement

Feb 21, 2025

“In the end, judgment comes first. And that means hiring is a gut decision. As much science as people want to try to pour into the hiring process, art always floats to the top. This is especially true when hiring at the executive level. The people who make the final calls — the ones who are judged on outcome, not…”

Lenny’s Podcast72 min

How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products

Dmitry Zlokazov · May 15, 2025
Key learnings
  • Treat product managers as end-to-end owners of their area, closer to local CEOs, with authority over the roadmap, team direction…
  • Hire for raw intellect and an unquenched hunger to build things, rather than for years of experience, since experienced hires…
  • Look for people who have founded startups or worked as tech co-founders, since they tend to be hands-on across many areas and…
Lenny’s Podcast145 min

Making Meta

Boz · Mar 3, 2024
Key learnings
  • Ask your manager for help earlier; your job is to get the work done well, and managers hold tools and context you may be missing.
  • Frame updates for busy leaders with 'no response required' messages, and say exactly where you are blocked and what specific help…
  • Communication is the job: your impact comes only through artifacts or words that move other people, and when things fail, examine…
Lenny’s Podcast98 min

Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member

Uri Levine · Jun 9, 2024
Key learnings
  • Start with a meaningful problem you feel personally passionate about, since the journey is long and hard and passion sustains…
  • Validate a problem by speaking with many people outside your close circle; if they describe the problem in their own words, it is…
  • Expect a journey of failures and iterate quickly; failing fast leaves time for more attempts, which raises the odds of success.
Lenny’s Newsletter♥ 97

When they hired their first PM

Nov 14, 2023 · 16 min
Subscriber post — summary only

Lenny Rachitsky surveys about 30 companies on when they hired their first product manager, finding the typical wait was two to three years, often before product-market fit. The post shows that someone always does PM…

Lenny’s Newsletter · Free post♥ 306

How Perplexity builds product

Apr 30, 2024 · 15 min

Lenny Rachitsky interviews Johnny Ho, co-founder and head of product at Perplexity, about how a fast-growing AI search company builds product with a very small team. Perplexity uses AI to answer its own operational…

SVPG · Marty CaganMay 30, 2013

Funnels vs. Umbrellas

May 30, 2013

Marty Cagan argues that product managers face a constant flood of requests from well-meaning colleagues, and that a product manager who simply funnels all of them into the roadmap will slowly kill the product. He…

Lenny’s Podcast98 min

Building a meaningful career

Jason Shah · Sep 18, 2022
Key learnings
  • Reframe pushback as shifting direction toward shared goals: first identify what the other person actually cares about, then align…
  • Use Amazon's working-backwards PR/FAQ: write the press release, customer quote, and leadership quote before building, forcing…
  • Cut vague adjectives like 'great' and replace them with concrete numbers and specifics, since fewer, heavier words force sharper…
Lenny’s Podcast124 min

Behind the founder: Drew Houston (Dropbox)

Drew Houston · Jan 9, 2025
Key learnings
  • Viral growth can be engineered: Houston credits a demo video, referral loops, and a beta waitlist that grew from 5,000 to 85,000…
  • When a product is broadly useful, competitors can bundle it free into their platforms; Houston argues the real defense is…
  • Borrow strategy from classic books: Houston credits Playing to Win and Only the Paranoid Survive for pushing him to narrow focus…
Lenny’s Podcast87 min

Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more

Gokul Rajaram · Jun 13, 2022
Key learnings
  • Do core work well but stay curious about other teams; serendipity and relationships built by helping people often create the next…
  • When choosing a company, prioritize a founder who authentically lives the mission, a problem you feel energy for, and a company…
  • Early-stage teams should plan weekly, then add quarterly and annual layers as they grow; keep tooling simple like a spreadsheet…
Lenny’s Podcast128 min

The rituals of great teams

Shishir Mehrotra · Aug 14, 2022
Key learnings
  • Map your product's growth as loops rather than linear funnels, and draw a diagram of how users bring in other users; Shishir says…
  • Remove friction from the moment users share, as Coda did by charging only for document makers, not for people they share with.
  • Treat publishing as a discovery channel: users who publish something useful for their niche can expose the product to new…
Lenny’s Newsletter♥ 33

Setting goals - Issue 23

Apr 29, 2020
Subscriber post — summary only

Lenny Rachitsky argues that a product leader's core job is aligning everyone on the same direction, and that goals are the tool for this. He places goals in a chain from mission to vision to strategy to goals to…

Lenny’s Podcast87 min

Netflix CPTO on AI and the future of product and tech roles

Elizabeth Stone · Jul 19, 2026
Key learnings
  • Expect a 'storming' phase with new technology; don't abandon AI, but be deliberate about capturing benefits while limiting costs…
  • Let product, design and data people prototype early against a clearly defined business problem, while still working with…
  • Invest in source-of-truth data, guardrails for shipping and testing, and review processes where AI output needs verification, and…
SVPG · Marty CaganNov 30, 2018

Common PM Problem Areas

Nov 30, 2018 · 5 min

Marty Cagan describes the most common confusions he sees in product teams, drawn from a dinner conversation with product leaders who recognized the same patterns. He argues that product teams should discover solutions…

Lenny’s Podcast97 min

Julie Zhuo on accelerating your career, impostor syndrome, writing, building product sense, using intuition vs. data, hiring designers, and moving into management

Julie Zhuo · Jun 7, 2022
Key learnings
  • Growth often comes from being in uncomfortable, unfamiliar situations; Julie notes that feeling like an imposter tends to…
  • Seek environments that are scaling, since growing companies create more opportunities to volunteer for new responsibilities and…
  • Share your struggles openly with peers, mentors, and reports; vulnerability builds deeper connections and lets others help you…
Lenny’s Podcast102 min

How to build a powerful marketing machine

Emily Kramer · Sep 11, 2022
Key learnings
  • Think of marketing as fuel (the content, positioning and assets that add value) and engine (distribution, tracking and ops), then…
  • Prioritize hiring for the business model, such as top-down sales versus product-led growth, over matching industry or audience…
  • Your first marketer should ideally be a 'pie-shaped' generalist with deep expertise in one area, usually product marketing, plus…
Lenny’s Podcast112 min

The secret to better AI prototypes: Why Tinder’s CPO starts with JSON, not design

Ravi Mehta · Sep 29, 2025
Key learnings
  • Startups win on latency, the speed from idea to validated result, not raw velocity; design tests so you can learn in days rather…
  • Early-stage companies lack the traffic for statistically significant experiments, so favor conviction built from enough data over…
  • Build an early-stage network of founders, angels, and builders early, since large-company connections often prefer staying in…
Lenny’s Podcast115 min

Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more

Kayvon Beykpour · Apr 28, 2024
Key learnings
  • Treat sacred cows as a built-in roadmap: list what the org believes can't change, then start challenging those assumptions one by…
  • Culture change requires alignment from the top; without leadership backing, pockets of the company advocating for change get…
  • Optimizing the core experience can reignite growth, but balance it with a portfolio of bold bets that add genuinely new…
Lenny’s Podcast100 min

Jenny Wen

Jenny Wen · Mar 1, 2026
Key learnings
  • Classic linear design process (research, diverge, converge) is breaking down as engineers ship prototypes quickly; designers…
  • Design work is splitting into two modes: supporting implementation and setting a vision, where the vision now often spans three…
  • Designers can use coding tools to do last-mile polish and prototype in real code, rather than waiting on engineers for every…