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
Lenny’s Podcast71 min

How to sell your ideas and rise within your company

Casey Winters · Jul 21, 2022
Key learnings
  • Escalate problems to leadership early so they can help change circumstances, rather than silently absorbing them; leaders can't…
  • Structure upward communication to start at the last point the audience already agrees with, not at the chapter-six detail or with…
  • Prepare for important meetings by role-playing each attendee and listing every possible question, ensuring you have the data to…
Lenny’s Podcast160 min

Improve strategy, influence, and decision-making by understanding your brain

Evan LaPointe · Aug 11, 2024
Key learnings
  • Send questions to the right mental mode: most people over-rely on fast, recall-based thinking, so deliberately route problems to…
  • Start meetings with priming, stating the context, shared goal, and guiding principles before jumping into decisions; mismatched…
  • Know your own personality and openness level, then be vulnerable with your team about how you naturally react to abstract vision…
Lenny’s Podcast82 min

The happiness and pain of product management

Noam Lovinsky · Mar 17, 2024
Key learnings
  • Advocate for what is best for the business even when it means shutting down your own project; in healthy organizations, that…
  • Don't hesitate to ask for a different reporting structure if it will make you more productive; Noam layered himself under a peer…
  • Set guiding principles for trade-offs, such as serving customers first, then supply, then the company, to resolve thorny…
Lenny’s Podcast101 min

Becoming a conscious leader: Leading without fear, finding your life’s objective function, and getting better at vision and strategy

John Mark Nickels · Oct 6, 2024
Key learnings
  • Treat leadership as any influence you have, not just formal management, and take responsibility for how you show up with others.
  • When stressed in high-stakes meetings, first allow the emotion and thought rather than fighting it, since resisting it tends to…
  • Stop seeking approval or self-worth from presentations and outcomes; anchoring to the mission and the product often improves both…
The Beautiful Mess · John Cutler♥ 48

TBM 426: The Trouble With Mirrors

Jun 16, 2026

John Cutler examines the difference between using mirrors and practicing mirroring, two ways of reflecting back what teams and people do. He describes how his own thinking about this distinction has evolved over the…

Lenny’s Podcast108 min

Bending the universe in your favor

Claire Vo · Apr 7, 2024
Key learnings
  • Know what you want from your career and your next role, and ask for it clearly, framed around how the role solves a real problem…
  • Time promotion conversations to the company's talent calendar and pitch concrete org-level gaps you can fill, such as an org…
  • Lean into your zone of genius by auditing your calendar, grouping activities by energy, and deliberately protecting time for the…
Lenny’s Podcast99 min

The engineering mindset

Will Larson · Jan 7, 2024
Key learnings
  • Treat engineers as capable adults by giving them hard problems and accountability, which lets them grow into senior leadership…
  • Build simple stock-and-flow models of processes like hiring pipelines, then compare them against historical data to find where…
  • Write your engineering strategy down, even imperfectly; an unwritten strategy cannot be debugged or improved, and every function…
Lenny’s Podcast116 min

The art of influence: The single most important skill that AI can’t replace

Jessica Fain · Mar 22, 2026
Key learnings
  • Treat stakeholder conversations as discovery interviews: go in to learn and strengthen your plan, not simply to get approval for…
  • Remember executives have chaotic calendars and little context on your topic, so spend under 60 seconds at the start restating why…
  • Ground your pitch in the executive's success metrics and board pressures, and show explicitly how your proposal moves those…
SVPG · Marty CaganJul 30, 2020

Keys To Successful Transformation

Jul 30, 2020 · 6 min

Lea Hickman and Marty Cagan argue that many company transformations to empowered product teams fail because key conditions are missing. They present ten keys, spanning senior leadership support, reframing technology as…

SVPG · Marty CaganApr 22, 2019

Coaching Tools – The Plan

Apr 22, 2019 · 15 min

Marty Cagan continues his coaching series by describing how managers can help product managers close specific skill gaps identified in an earlier assessment. He covers product knowledge (users, data, industry, business…

Product Talk · Teresa TorresOct 5, 2012

Remembering Steve

Oct 5, 2012

“One year ago today, Steve Jobs passed away. I can't think of any other person of whom I feel more conflicted. It's hard to argue with Steve's results. After all, he brought us the candy-colored iMacs, the iPod, iTunes, the iPhone, the iPad, and so much”

Lenny’s Podcast115 min

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more

Alisa Cohn · Jan 5, 2025
Key learnings
  • Before a hard conversation, identify what you're making it mean (e.g., fear of upsetting someone) and check your intent: the aim…
  • Frame performance feedback around observable facts and expectations, citing what you've heard from multiple people, and keep your…
  • Build the relationship with positive, specific feedback regularly so people hear criticism as coming from someone who wants to…
Lenny’s Newsletter♥ 225

How to get better at influence

Sep 20, 2022 · 12 min
Subscriber post — summary only

Lenny uses the Lord of the Rings, especially Frodo's journey, as a lens for how product managers can build influence without relying on formal authority. He walks through seven strategies, each illustrated with Airbnb…

SVPG · Marty CaganMar 10, 2021

Best vs. Rest FAQ

Mar 10, 2021 · 4 min

Marty Cagan answers reader follow-up questions after his previous article on the two product worlds he works in. He points readers to books that explain the cultures and product practices of Apple, Amazon, Google and…

Lenny’s Podcast87 min

Inside TikTok: Culture, strategy, monetization, and more

Ray Cao · Mar 7, 2024
Key learnings
  • Succeeding in global markets requires sending people in, hiring local talent, and understanding local culture, since the…
  • Adopt a 'context, not control' mindset: give teams full information and ownership, then let them proactively think and reactively…
  • Hire for curiosity, discipline, and prioritization skill; Cao notes that hiring quality over speed is a mistake he made early on.
SVPG · Marty CaganMay 14, 2020

Meaningful Transformation

May 14, 2020 · 4 min

Marty Cagan addresses the common question of how organizations move from feature teams to empowered product teams. He argues that Agile delivery methods alone are insufficient and that transformation depends first on…

Lenny’s Podcast106 min

Competing with giants: An inside look at how The Browser Company builds product

Josh Miller · Mar 19, 2023
Key learnings
  • Optimize for the feeling you want users to have (joy, speed, surprise, focus) and use metrics as an honesty check rather than the…
  • Track one tight engagement metric that captures retention, engagement, and growth together, such as how many users return five of…
  • Hire people who show up with heartfelt intensity and something to prove, then give them an ambitious prompt and get out of their…
Lenny’s Podcast101 min

Building Anchor, selling to Spotify, and lessons learned

Maya Prohovnik · Sep 28, 2023
Key learnings
  • Dogfood your product by creating content with it yourself, since building creator tools without living the creator experience…
  • Ensure the team experiences the product's pain directly, for example by having engineers and PMs make their own podcasts, to…
  • Balance data and gut instinct by treating your intuition as a legitimate data point, explaining its reasoning with evidence…