Lenny's Reads

When their team underperforms, most managers jump straight to blaming people. Molly Graham—who's worked alongside Mark Zuckerberg, Sheryl Sandberg, and Chamath Palihapitiya—explains how that's one of the biggest leadership traps there is. In this episode, she shares the Waterline Model: a diagnostic model to help uncover the real source of team problems, before touching an org chart.

In this episode, you'll learn:
• Why blaming people for structural problems is one of the biggest leadership mistakes
• The four layers of the Waterline Model, and why that order matters
• Why you should always "snorkel before you scuba"
• How self-preservation can be a rational response to a faulty environment
• How to make clean, decisive calls when you finally reach the individual layer

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References:
• "Give Away Your Legos": https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/
• Glue Club: https://glueclub.com/
• Molly Graham: https://www.linkedin.com/in/mograham/
• Molly Graham on Lenny's podcast: https://www.youtube.com/watch?v=twzLDx9iers
• Lenny's Product Pass: https://www.lennysproductpass.com/

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Read the full newsletter: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working

Subscribe to Lenny's Newsletter: https://www.lennysnewsletter.com/subscribe

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Welcome to Lenny's Reads, where every week you'll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot.


To hear more, visit www.lennysnewsletter.com

What if you could get line-by-line feedback on every interview answer you gave, predict questions before you walk in, and surface stories you didn't know you had? Noam Segal, Lenny's Community Research Lead, interviewed over 30 tech professionals about how they use AI throughout the interview process, and used the findings to build a free Claude Code-based interview coach. His coach encodes every successful interview technique he uncovered (and then some), making it an invaluable tool you can plug into your job search today.

In this episode, you'll learn:
· Why interview prep is broken (and why there's no usable feedback loop)
· How the most successful candidates built AI systems to close the gap
· What the free AI Interview Coach does and how to set it up
· How to stop sounding like every other candidate who prepped with AI
· The action checklist for before, during, and after every interview

References:
· Claude: https://claude.ai/
· Granola: https://granola.ai/
· Claude Code Interview Coach (Github link): https://github.com/noamseg/interview-coach-skill
· Lenny's Product Pass: https://lennysproductpass.com/
· Noam Segal: https://www.linkedin.com/in/noamsegal
· PM Interview Copilot: https://www.benerez.com/copilot
· Product sense guide: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering

Read the newsletter
https://www.lennysnewsletter.com/p/how-to-use-ai-in-your-next-job-interview

Subscribe to Lenny's Newsletter
https://www.lennysnewsletter.com/subscribe

Subscribe
YouTube: https://www.youtube.com/@lennysreads
Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693
Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj
Substack: https://lennysreads.com/

Follow Lenny
Twitter: https://twitter.com/lennysan
LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
Podcast: https://www.youtube.com/@lennyspodcast

About
Welcome to Lenny's Reads, where every week you'll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot.


To hear more, visit www.lennysnewsletter.com

Ever run an AI analysis on customer data, only to discover the numbers were fabricated and the insights completely generic? In this episode, Caitlin Sullivan, a user-research veteran who's trained hundreds of product and research professionals, shares her four prompting techniques for getting trustworthy, actionable insights out of any LLM. After 2,000+ hours of testing customer discovery workflows with AI, she's identified the failure modes that break AI analysis and the reliable fixes for each one.

In this episode, you'll learn:
• How to catch the two types of AI quote hallucinations
• Why AI defaults to useless generic themes and insights
• Which LLM is best for analysis work (and which one fabricates the most)
• How to turn vague signal into actual decision clarity
• The final verification pass that stress-tests everything before it hits a deck
Referenced:
• Caitlin Sullivan: https://www.linkedin.com/in/caitlindsullivan/
• Claude Code for Customer Insights (Maven course): https://maven.com/caitlin/claude-code-insights
• Claude: https://www.anthropic.com/claude
• ChatGPT: https://chatgpt.com/
• Gemini: https://gemini.google.com/
• NotebookLM: https://notebooklm.google.com/
• Maze: https://maze.co/
• Whoop: https://www.whoop.com/
Read the newsletter: https://www.lennysnewsletter.com/p/how-to-do-ai-analysis-you-can-actually
Subscribe to Lenny’s Newsletter: https://www.lennysnewsletter.com/subscribe
Subscribe:
• YouTube: https://www.youtube.com/@lennysreads
• Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693
• Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj
• Substack: https://lennysreads.com/
Follow Lenny
• Twitter: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
• Podcast: https://www.youtube.com/@lennyspodcast
About
Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot.


To hear more, visit www.lennysnewsletter.com

If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.com

Dr. Marily Nika, longtime AI PM at Google and Meta, shares a simple weekly ritual that rapidly builds AI product sense – the ability to translate probabilistic model behavior into products people can trust. In this episode, Marily walks through the framework for uncovering failure modes before users do.

Listen now: YouTube | Apple | Spotify

In this episode, you’ll learn
• Why Meta added “Product Sense with AI” to its PM interview loop
• The rituals that surface hidden failure modes
• Why generative models confidently invent structure when confronted with mess
• What minimum viable quality (MVQ) means and how to define three critical thresholds
• Five strategic context factors that raise or lower your quality bar
• Why you need to estimate your AI feature’s cost envelope early
• How to design guardrails that protect users from model shortcomings
• Four patterns that cover most real-world failure cases

Referenced
• AI PM Bootcamp & Certification
• AI Product Sense & AI PM Interview prep
• Dr. Marily Nika: https://www.linkedin.com/in/marilynika/
• How to build AI Product sense (Part 1)
• Marily’s AI Product Academy Newsletter
• Thriving as a senior IC PM in the AI era

About
Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot.


To hear more, visit www.lennysnewsletter.com

If you’re a premium subscriber, add the private feed to your podcast app at add.lennysreads.com
Your product builder's Product Pass just got even better. In this episode, we introduce the seven new premium partners joining the Product Pass, bringing the total value of a paid newsletter subscription to over $25,000. We cover all the new products, what they do, how people are using them, and the key details you need to know before subscribing.

Listen now: YouTube | Apple | Spotify

In this episode, you’ll learn:
• Key features of each of the seven new products
• Applicable, real-world examples of how people are using them
• Which products are exclusive to Insider subscribers

References:
• Affinity
• Amp
• Canva Business
• Duolingo
• ElevenLabs
• Every
• Factory
• Flourish
• Framer
• Harvey
• Kernel
• Leonardo.Ai
• Lovable
• Manus
• Meta
• Metabase
• Mozart AI
• n8n
• Nvidia
• Perplexity
• Product Pass codes
• Railway
• Sentry


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