Lenny’s Podcast102 min
Deb Liu · Aug 4, 2022
Key learnings- Treat your career like a product: write down what success looks like in five years, the milestones and skills needed, and measure…
- Keep balancing learning and impact; the expert you are today will be outpaced by someone still actively learning from the best…
- Treat setbacks as stepping stones; people who recover from hard feedback and failed products often become the strongest leaders.
Lenny’s Podcast115 min
Kevin Yien · Aug 18, 2024
Key learnings- Consider entering product management from engineering, design, or sales, since those roles teach you the front-line work a PM…
- Treat product management as converting a team's potential energy into realized customer value, and only add PMs where that work…
- Write clearly and compellingly enough that others can act on it; Kevin argues a PM who cannot sell or support their own product…
Lenny’s Podcast93 min
Tamar Yehoshua · Sep 26, 2024
Key learnings- Excel in your current role before chasing the next one; advancement follows demonstrated impact, not just hitting goals or…
- Evaluate a potential employer's engineering partner before joining, since great ideas that can't be built lead nowhere.
- Don't assume a company must be well run to succeed; hyper-growth firms often run chaotically, but prioritize companies whose…
Lenny’s Podcast120 min
Molly Graham · Jan 4, 2026
Key learnings- Keep handing off the work you've mastered so you can take on the next, bigger challenge; the job keeps growing, so you must keep…
- Name and externalize the emotional reactions to change, then give them about two weeks; anything lasting longer deserves a real…
- When a team struggles, snorkel before you scuba: check structure (goals, roles, expectations) and team dynamics before blaming…
The Looking Glass podcastApr 14, 2026
Apr 14, 2026
Key learnings- World-class designers are distinguished by judgment and taste, not just the ability to execute polished visuals.
- Excellent designers obsess over the underlying problem before jumping to solutions, which separates them from those who iterate…
- Strong designers can articulate why a decision is right, tying craft choices back to user needs and business constraints.
Lenny’s Podcast72 min
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 Podcast153 min
Marc Andreessen · Jan 29, 2026
Key learnings- Expect AI to make already-skilled people far more capable; the gains are largest for those who pair deep expertise with AI tools.
- Rather than fearing job loss, focus on task loss: jobs persist while the individual tasks composing them shift, which is how…
- Combine at least two or three domains deeply (e.g., coding, product, design); the combination of skills creates far more value…
Lenny’s Podcast26 min
Interview Q Compilation · Nov 29, 2023
Key learnings- Ask 'To what do you attribute your success?' and watch for self-awareness and curiosity rather than an answer like 'luck' (Eeke…
- Ask 'What's the hardest thing you've ever done?' to learn how a candidate defines difficulty, how they overcame it, and how much…
- Use the teleportation-device 'Eigenquestion' exercise: candidates may ask only two questions, then must plan, revealing how they…
Lenny’s Podcast118 min
Tom Verrilli · Aug 2, 2026
Key learnings- Don't hire a PM by default for every team; hire one only where there is a specific need, since engineers and designers can often…
- Product management is a trade built through repetition, so spreading PM reps to engineers and designers strengthens their…
- Map PMs to problems and six-month company priorities rather than fixed teams, so ownership follows the work and people build…
Lenny’s Podcast78 min
Jackie Bavaro · Jun 16, 2022
Key learnings- Ask your manager directly how to prepare for a future promotion, framing the goal in the future so the manager becomes an ally…
- Treat a strategy as three parts: a vision, a strategic framework with pillars and bets, and a backward-working roadmap used as a…
- A roadmap in strategy is a sanity check, not a commitment; if it can't reach the vision in time, that signals bigger bets or more…
Lenny’s Podcast68 min
Brandon Chu · Jun 27, 2022
Key learnings- Treat domain expertise as table stakes; to reach the highest levels, lean into founder skills like storytelling, motivating…
- Think of the PM role as helping teams ship the right thing at the right time in the right way, acting as a servant leader rather…
- Set annual directional plans but expect them to change; avoid sunk-cost fallacy and be willing to throw away work when the world…
Lenny’s Podcast92 min
Joe Hudson · Aug 8, 2024
Key learnings- Treat the critical inner voice as usually wrong and unhelpful; rather than trying to silence it, respond to it differently…
- Respond to a fearful inner critic with compassion, such as acknowledging it is scared and that you are there with it, instead of…
- Approach emotional change as experimentation and self-discovery, not self-improvement, since failed attempts at self-improvement…
Lenny’s Podcast108 min
Cat Wu · Apr 23, 2026
Key learnings- Shorten the path from idea to user: AI-era timelines have shrunk from six months to days or a week, so PMs should focus on…
- Ship features as clearly labeled research previews to lower the commitment of launching and get fast user feedback that can be…
- Set a clear, specific goal for who the key user is and what success means, which rules out many approaches and speeds decisions.
Lenny’s Podcast87 min
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 Podcast91 min
Sanchan Saxena · Jul 5, 2022
Key learnings- Careers rarely follow a plan; Sanchan advises taking little bets, learning fast, and pivoting rather than over-planning a…
- Choose a role that maximizes how fast you learn product management, and match the startup versus big-company choice to whether…
- During a crisis, Airbnb replaced fixed teams with one company-wide team and two-week planning cycles, reacting to fast-changing…
Lenny’s Podcast86 min
Manik Gupta · Jul 14, 2022
Key learnings- Surround yourself with exceptional people early in your career and stick with them over the long term, since shared trust built…
- Consumer products are harder than they look because builders are not typical users; you cannot force adoption, so virality and…
- Build consumer products for a global audience from day one, localizing language, pricing, and legal requirements while avoiding…
Lenny’s Podcast103 min
Laura Schaffer · Mar 9, 2023
Key learnings- Build career momentum beyond your manager by learning your customers deeply and sharing those insights, which makes you a go-to…
- Share customer insights regularly and make them visible; a recurring voice-of-the-customer report can grow into a forum that…
- Expect many ideas to be rejected; treat each refusal as a chance to bring better information, since leaders value insights they…
Lenny’s Podcast109 min
Benedict Evans · May 31, 2026
Key learnings- Treat AI as roughly as big as the internet or mobile, and recognize we are early, like 1997, with most applications not yet built…
- Expect adoption to be very uneven; survey data shows many people are not using AI at all, so don't assume the people in your…
- Ask whether a job is a task that can be automated or a deeper outcome; consultants and professionals are hired for judgment…
Lenny’s Podcast86 min
Andy Johns · Sep 10, 2023
Key learnings- Treat persistent disruption to sleep, relationships, physical health, and daily routines as a clear signal that something needs…
- Recognize that many high achievers tie self-worth to achievement; identify those adaptations that once helped you but may now be…
- Start with a therapist or counselor, and choose based on feeling safe and comfortable, ideally with someone intellectually at…
Lenny’s Podcast145 min
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 Podcast118 min
Mayur Kamat · May 22, 2025
Key learnings- Join fast-growing companies, since learning compounds much faster when you ship and learn daily rather than over multi-year…
- Identify your genuine strengths, through structured assessments or peer feedback, and seek roles where success depends on using…
- Early in your career, don't optimize for compensation; most earnings tend to come later, so prioritize learning and fit.
Lenny’s Podcast93 min
Chip Conley · Aug 3, 2025
Key learnings- When working for a founder, open meetings by aligning on the goal, what defines success, and what the meeting must accomplish…
- Build credibility with demanding leaders by getting close to customers, such as visiting hosts in their homes, so your input…
- Keep decks short and principle-focused so they still make sense when a combustible founder derails the meeting.
Lenny’s Podcast80 min
Adam Fishman · Oct 13, 2022
Key learnings- Use a competency model (growth execution, customer knowledge, growth strategy, communication and influence) to hire for a…
- Before hiring a growth leader, agree on what you need and where the gaps are, and use the model as a reverse interview to see…
- Give specific feedback by naming the exact competency to improve, instead of vague comments like 'be more strategic'.
Lenny’s Podcast142 min
Matthew Dicks · Dec 15, 2023
Key learnings- Build every story around one five-second moment of transformation or realization, and make the rest of the story context that…
- Start stories as close to the end as possible, because the ending moment determines what you need to say and where to begin.
- Apply the dinner test: tell stories the way you would at a dinner table, only slightly elevated, without performance tricks like…