Lenny’s Podcast115 min
Tom Conrad · Nov 26, 2023
Key learnings- Choose where to work by the people you'd collaborate with, not just the product; your satisfaction tracks team relationships more…
- Trust your gut about a team's values and working style early; Conrad says he has consistently sensed mismatches before joining…
- Build a model of the whole business equation (investment in, returns out, over a time horizon) so you can see which levers have…
Lenny’s Podcast107 min
Luc Levesque · Jun 15, 2023
Key learnings- Focus relentlessly on impact over activity: measure outcomes against the north-star metric rather than hours worked or work…
- Hire the top 1% by looking for repeated 'signs of excellence' in a candidate's history, such as multiple standout achievements…
- Recruit with the whole executive team and involve the candidate's spouse or family, since changing companies is a family…
Lenny’s Podcast91 min
Judd Antin · Jan 4, 2024
Key learnings- Much research sits in a 'middle range' of questions that are interesting but rarely drive business decisions; push for macro…
- Integrate researchers from the beginning of product processes rather than calling them in at the end as a service function; their…
- Watch for 'user-centered performance': late-stage requests to validate assumptions or check boxes that signal customer obsession…
Lenny’s Podcast93 min
Ken Norton · Jul 24, 2022
Key learnings- Executive coaching is a partnership where the client defines success; the coach brings listening, curiosity, and challenge rather…
- Advice often delivers a short-lived boost, like cotton candy; lasting growth usually requires confronting the underlying problem…
- Leadership shifts are largely internal: reframing your operating system matters as much as learning new frameworks once you reach…
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 Podcast124 min
Jake Knapp + John Zeratsky · Feb 11, 2024
Key learnings- Start each day by choosing a highlight: imagine the day is over and decide what you'd want to call the highlight, then protect a…
- Don't rely on willpower; change your environment by logging out of apps, deleting infinity-pool apps from your phone, or adding…
- Use your calendar as a design tool by blocking focus time, meals, exercise, and personal priorities, then adjust the template…
Lenny’s Podcast86 min
Annie Pearl · Feb 26, 2023
Key learnings- When sharing a scheduling link, first invite the other person to share their availability, and paste your open times directly…
- Break into product via internal transfer: show curiosity, help with product work on the side, and build relationships with PMs…
- Start from a clear product strategy that defines where you play and where you don't, including the markets, segments, and…
Lenny’s Podcast92 min
Petra Wille · Nov 27, 2022
Key learnings- Define what a good product person looks like in your specific context, since many leaders only hold this as an implicit feeling…
- Start coaching with a development plan for each PM, even before a formal assessment, because most people already know what they…
- Identify the next bigger challenge for each direct report each quarter and deliberately assign it to help them grow faster.
Lenny’s Podcast119 min
Sriram and Aarthi · Mar 12, 2023
Key learnings- Meet peers across your org for coffee with no agenda, asking about their work and who else to meet; two coffees a week compounds…
- Follow up after good first meetings and check in every six months or so; most people never follow through, which wastes the…
- Put your work out publicly (threads, posts, talks, GitHub, video); it acts as a signal that attracts serendipitous opportunities…
Lenny’s Podcast98 min
Kenneth Berger · May 19, 2024
Key learnings- Treat your complaints as clues: every complaint implies a dream, so reverse it into the better future you actually want.
- Articulate your wants out loud, checking whether the dream is both inspiring and credible rather than embarrassing or unrealistic.
- Hold a high bar for yes: anything short of an enthusiastic 'hell yes' should be treated as a no and explored further.
Lenny’s Podcast112 min
Melissa Perri · Jul 28, 2022
Key learnings- The product owner role came from Scrum as a way to help developers prioritize work, not from product management, so it often…
- Frameworks like SAFe are heavily marketed and often adopted rigidly; Perri has seen most teams that found success end up ripping…
- Teams that already talk to customers and iterate quickly may not need a framework at all; the principle of shipping value and…
Lenny’s Podcast78 min
Jerry Colonna · May 8, 2025
Key learnings- Ask how you have been complicit, not responsible, in creating the conditions you say you don't want; this evokes personal agency…
- Use radical self-inquiry to examine what you claim to want versus what you actually feel, such as saying you dislike busyness…
- Notice whether your drive comes from proving your worth; separate the enjoyment of the work from the need to feel like somebody.
Lenny’s Podcast121 min
Molly Graham · Sep 27, 2026
Key learnings- Change is scary and hard, but leaning into it and letting go of old responsibilities is still the best way to grow, even as the…
- Name the emotions change brings, including grief for lost craft; leaders who normalize these feelings help people feel less alone…
- Treat AI like a lazy junior intern: give it context, review its output, and never ship its work unchecked, since accountability…
Lenny’s Podcast155 min
Hilary Gridley · Jun 15, 2025
Key learnings- When you feel criticized, skip litigating what others think and instead take one small action that demonstrates the opposite of…
- Use behavioral activation: act first on a small, concrete step, since action tends to lift mood and break negative spirals rather…
- Speak up in meetings with valuable input; fear of saying the wrong thing is the main blocker, and building the skill to take a…
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 Podcast64 min
Marily Nika · Feb 5, 2023
Key learnings- Avoid the shiny object trap: only add AI when there is a real, well-defined pain point worth solving, and identify the problem…
- Don't use AI for an MVP; fake the AI behavior with a clickable prototype and test desirability with users first.
- Use ChatGPT as a sounding board for sharpening mission statements and generating user segments, personas, and motivations, while…
Lenny’s Podcast100 min
Zevi Arnovitz · Jan 18, 2026
Key learnings- Start slowly with a ChatGPT project acting as a skeptical 'CTO' before moving to coding tools, gradually easing into code to…
- Capture ideas quickly as Linear issues using reusable slash commands, so you can pick them up later with context already gathered.
- Separate the workflow into explore, plan, execute, review, and document phases, and have the AI ask clarifying questions before…
Lenny’s Podcast134 min
Nabeel S. Qureshi · May 11, 2025
Key learnings- Define who your company is not for: Palantir screened for independent-minded, intellectually broad, intensely competitive people…
- Avoid meaningless principles like 'move fast'; write principles people can meaningfully disagree with, and pressure-test project…
- Use forward deployed engineers who are real builders empowered to create new product for a customer, working in person with the…
Lenny’s Podcast95 min
Donna Lichaw · Feb 25, 2024
Key learnings- Treat the stories you tell yourself as hypotheses: check them against real feedback from colleagues instead of assuming they are…
- Start leadership growth from the inside out: lead yourself first, then one-on-ones, teams, and the wider business.
- Ask how a limiting habit or belief, like imposter syndrome, currently serves you before trying to suppress it.
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 Podcast85 min
Roger Martin · Jul 25, 2024
Key learnings- Strategy is an integrated set of choices that compels desired customer action, since customers are the one thing a company cannot…
- Work through the five cascade questions together: winning aspiration, where to play, how to win, required capabilities, and…
- Winning requires being either differentiated or lowest cost; without one of those, competitors can keep pushing you back step by…
Lenny’s Podcast89 min
Matt Mochary · Nov 10, 2022
Key learnings- When you sense fear clouding judgment, make a low-stakes bet with a peer on the opposite prediction; Mochary says fear has…
- Deliver layoff news one-on-one, never via email or group chat, since impersonal delivery is what turns layoffs into anger and…
- Separate the decision from its implementation: decide based on what serves the customer, then address the hurt of each affected…
Lenny’s Podcast114 min
Christopher Miller · Aug 10, 2023
Key learnings- Take ownership of problems nobody has claimed; a radical accountability mindset can surface opportunities the business hasn't…
- Prioritize relentless curiosity and resilience when hiring or growing as a PM, since most growth experiments fail and you need…
- Talk directly to customers and to non-customers; usage data shows what users do, but only qualitative conversations reveal why.
Lenny’s Podcast94 min
Hari Srinivasan · Jul 16, 2023
Key learnings- Anchor decisions in a single clear North Star, such as connecting people to economic opportunity, so cross-marketplace tradeoffs…
- In complex ecosystems, map second- and third-order effects of every change, since a feature can shift how members perceive and…
- Name one decision-maker per decision (RAPID-style recommender, agreer, decider, input roles) and move to a call after a few email…