Lenny’s Podcast71 min
Wes Kao · Apr 6, 2025
Key learnings- Spend less time on why an idea matters and more on the specific how: concrete steps, nuances, and examples that let people apply…
- Cut backstory and preamble; start right before the juicy part of the story, as Wes puts it, 'right before you get eaten by the…
- Recognize that formats like Twitter or keynotes allow more BS, while courses and cohort settings demand rigor because students…
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…
Lenny’s Podcast108 min
Kim Scott · Dec 10, 2023
Key learnings- Radical candor means caring personally while challenging directly; missing the first yields obnoxious aggression, missing the…
- Don't ask 'Do you have any feedback for me?'; instead ask a specific question like 'What could I do or stop doing that would make…
- Give feedback immediately, in person or by phone rather than text or Slack, and use context, observation, result, next step…
Lenny’s Podcast99 min
Nancy Duarte · Jun 1, 2023
Key learnings- Make your audience the hero of the story and approach every presentation with empathy, since the audience ultimately holds the…
- Position yourself as the mentor who helps the audience get unstuck, offering them a practical tool and an inner resolve for the…
- Use the 'what is / what could be / new bliss' contrast structure to build tension and longing for a future state, even in short…
Lenny’s Podcast143 min
Tristan de Montebello · Oct 13, 2024
Key learnings- Treat speaking as a meta skill: improving it tends to lift confidence and results across work, relationships and daily life.
- Use enjoyment as a barometer; if practice or speaking feels unpleasant, you are probably overthinking or doing it wrong.
- Focus on root causes like pressure and self-trust rather than surface symptoms such as filler words or rushing.
Lenny’s Podcast79 min
Julian Shapiro · Sep 25, 2022
Key learnings- Pursue product-led acquisition by designing features where users naturally invite others, such as settling debts, sharing…
- Build user state, like reputation, audience, or social graphs that cannot transfer off-platform, so accumulated investment makes…
- Prefer evergreen topics and keep updating old writing, since Julian treats his handbooks and posts as living assets rather than…
Lenny’s Podcast97 min
Matt Abrahams · Mar 31, 2024
Key learnings- Visualize the whole experience, from walking to the stage to stepping off, including the audience responding well, to desensitize…
- Prepare in order to be spontaneous; practice is what makes improvisation and on-the-spot speaking go well, as it does in…
- Strive for connection over perfection by daring to be dull: just answer the question and stop judging every word, which frees up…
Lenny’s Podcast122 min
Mihika Kapoor · Apr 21, 2024
Key learnings- Build a vision that ties together a user pain point, a proposed solution, and a proof point such as a testimonial or prototype…
- Pull research, design, and engineering feasibility into the vision early so it reflects what users feel and what the team can…
- Lean on prototypes and mocks before a project gets approved; seeing and feeling the future often persuades more than…
Lenny’s Podcast116 min
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…
Lenny’s Podcast76 min
Lulu Cheng Meservey · Mar 23, 2023
Key learnings- Make ideas spread by making them memorable and giving people a reason to repeat them, such as humor, a vivid mental image, an…
- Test a catchphrase by asking whether a second-grader could understand it immediately; avoid inside jokes that only make sense…
- Treat making mistakes of commission rather than omission as the better bet, since visible errors can be learned from while…
Substack podcastDec 27, 2025
Dec 27, 2025
Key learnings- Writing can sharpen thinking by forcing you to make vague ideas explicit and expose gaps in your reasoning.
- The claim 'writing is thinking' is useful but overextended; not all thinking happens through writing, and writing alone does not…
- Treat writing as one tool among several for thinking, alongside conversation, sketching, and deliberate reflection.
Lenny’s Podcast96 min
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…
Lenny’s Podcast71 min
Andy Raskin · May 28, 2023
Key learnings- Replace the 'arrogant doctor' pitch (problem, solution, why we're better) with a story that opens by naming a shift from an old…
- Name the old game in a few concise words, such as 'transactions' or 'opinions', since compact labels make the shift easy to…
- Show that winners are already playing the new game, and frame the stakes as a clear choice between a very negative and a very…
Lenny’s Podcast87 min
Anneka Gupta · Oct 17, 2024
Key learnings- Being strategic means pairing a compelling, simple 'why' behind decisions with the courage to champion hard, long-term changes…
- Reframe high-stress situations by asking what you can learn and by bringing humor into meetings, since your mood shapes how the…
- Summarize what others have said in meetings and end with a question inviting agreement or dissent; this builds trust and moves…
Lenny’s Podcast95 min
Jeffrey Pfeffer · Jun 13, 2024
Key learnings- Political skill is linked to higher pay, promotions, job satisfaction and lower stress, so treating influence as a learnable…
- Get out of your own way: stop pre-emptory apologizing, stop doubting you deserve your role, and avoid leaking disrespect or…
- Prioritize competence and respect over being liked; you were hired to get a job done, so doing the needed work matters more than…
Lenny’s Podcast133 min
Rachel Lockett · Nov 23, 2025
Key learnings- Coach instead of advising when the person has the context and skills to solve their own problem; advise only when urgency is high…
- Practice three levels of listening, especially level-three global listening that attends to emotions, body language, and context…
- Use the GROW model (goal, reality, options, way forward) as a flexible set of powerful questions to unlock someone's own solution.
Lenny’s Podcast85 min
Ian McAllister · Nov 20, 2022
Key learnings- New PMs should focus first on communicating, prioritizing, and executing, since other skills grow in importance with seniority.
- Answer first and then explain; when asked a 'when' question, give a date, and grade yourself after feedback to improve…
- Prioritization is a core PM skill across themes, projects, sequencing, scope, and personal time, and it strongly multiplies…
Lenny’s Podcast97 min
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 Podcast71 min
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 Podcast125 min
Ebi Atawodi · Dec 3, 2023
Key learnings- A vision should describe a picture of the future state, be lofty yet attainable, be free of today's technical limits, and be…
- Distinguish vision from mission: the vision is what the destination looks like, while the mission is the purpose and guiding…
- Write the vision as a 'once upon a time' story (current problem, a turning point, and the resulting changed world), or write the…
Lenny’s Podcast109 min
Ami Vora · Jun 23, 2024
Key learnings- Sublimate your ego: prioritize reaching the right outcome over being right, since others often hold information you lack.
- Respond to disagreement with curiosity by asking the other person to explain their reasoning, and pause before reacting to avoid…
- Keep product reviews short, bring a clear recommendation, and use them to calibrate on reusable principles rather than to approve…
Lenny’s Podcast115 min
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 Podcast113 min
Maggie Crowley · Nov 5, 2023
Key learnings- Great PMs simplify relentlessly: find the one thing to do and stick with it long enough to actually finish it.
- Read your documents out loud and cut anything complicated; if you can say it in conversation, write it that way.
- Follow up on results after launches by setting calendar reminders to check metrics weeks and months later, and share what you…
Lenny’s Podcast144 min
Phyl Terry · Sep 12, 2024
Key learnings- Join or form a small Job Search Council of six to eight peers who meet regularly, since shared accountability turns job-search…
- Write a short 'Mnookin two-pager' listing what you want and don't want, then refine it with peers before taking it to the market.
- Run a listening tour with reverse exit interviews, broader network, and recruiters, asking 'If you were in my shoes, how would…