Lenny’s Podcast129 min
Sam Lessin · Jan 15, 2026
Key learnings- Aim to enter a room with a low heart rate and an abundance mindset rather than scarcity, since the conversation is a…
- Arrive a little early, roughly 10 to 15 minutes, and never make a late guest feel bad; a simple apology is enough.
- When you forget someone's name, introduce your partner first and let the moment hang so the other person picks up the name, or…
Lenny’s Podcast78 min
Vikrama Dhiman · May 12, 2024
Key learnings- Early in your career, prioritize shipping concrete outputs and being useful to your team; strategic influence comes as you earn…
- Keep producing hands-on artifacts like PRDs, strategy docs, and briefs even as you grow senior, since quality artifacts signal…
- Work on your operating model: raise difficult issues without being difficult to work with, surface topics without centering…
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 Podcast70 min
Paige Costello · Jul 9, 2023
Key learnings- Plan on a rolling 12-month horizon, refreshed every six months, so the immediate half has higher confidence and the business…
- Structure planning in nested altitudes (company, pillar, area, team) with metrics at each level so every team knows the outcome…
- Use a broad-then-narrow process for each problem: choose the customer, then the problem, then the solution, and pick success…
Lenny’s Podcast77 min
Nikita Miller · Apr 6, 2023
Key learnings- Have product, design, engineering and data leaders each write expectations for their own role and for each other, then review…
- Revisit roles and responsibilities every few months, usually triggered by tension or missed work, with a quick retro when…
- Watch execution velocity and decision-making speed closely; outcomes matter, but shipping output quickly is the indicator that…
Lenny’s Podcast131 min
Dr. Becky Kennedy · Feb 1, 2026
Key learnings- Repair after a mistake, by owning your part and naming what you'll do differently, rebuilds trust; perfection is not the goal…
- Connect before correcting: join the other person's world first without an agenda, since connection builds the bridge that makes…
- Separate behavior from identity by assuming someone is good inside, which keeps conversations productive and makes defensiveness…
Lenny’s Podcast90 min
Camille Ricketts · Dec 11, 2022
Key learnings- Treat content like a product: define who the audience is and what painful job they need done before creating anything.
- Community-led growth works best when the product creates something users want to share, such as templates or creative workspaces.
- Measure brand discovery with net new visitors to your site month over month, rather than starting with rigid community ROI…
Lenny’s Podcast160 min
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 Podcast99 min
Ethan Evans 2.0 · Jan 14, 2024
Key learnings- Do your current job well first; you can't grow your career while your manager wishes you were different about your performance.
- Ask your manager directly how you can help them, then do what they ask even when the work is unglamorous.
- Once trust exists, tell your manager your specific career goal and ask what they need that would also advance you; managers help…
Lenny’s Podcast87 min
Yuhki Yamashata · Jan 8, 2023
Key learnings- Storytelling is a core PM skill; Yamashita suggests resetting your context and retelling the situation as if the listener knows…
- Own the 'why' of a product: when teams can't have detailed specs, a shared understanding of the problem lets people make good…
- Use the 'five whys' on problems, asking not just why a customer wants a feature but why they have the underlying problem in the…
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 Podcast78 min
Janna Bastow · Oct 16, 2022
Key learnings- Treat a roadmap as a prototype for your strategy: its value lies in the roadmapping process of sharing and testing assumptions…
- Replace timeline-based roadmaps with Now, Next, Later buckets so that not every item implies a due date, since uncertainty grows…
- Reserve firm dates for truly fixed constraints such as regulatory deadlines or seasonal rushes, and plan extra buffer and soft…
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 Podcast101 min
Camille Fournier · Sep 15, 2024
Key learnings- Share credit generously with engineers and give them room to present their own technical contributions rather than taking the…
- Show genuine interest in engineering details, even if you don't need to master them, since dismissing them signals a lack of…
- Avoid acting as a go-between for engineers and stakeholders; if you keep relaying questions back and forth, connect the people…
Lenny’s Podcast84 min
Raaz Herzberg · Nov 17, 2024
Key learnings- Early in a startup, look for signs of real pull, such as prospects asking about pricing, timelines, or introducing you to their…
- Be willing to say 'I don't understand' in product discussions; a healthy culture makes admitting confusion a strength, and…
- Run a high volume of customer conversations (10 to 15 a day in Wiz's case) to find what actually resonates rather than relying on…
Lenny’s Podcast99 min
Gergely · Nov 17, 2022
Key learnings- Build real depth in a specific field before writing about it, since credibility from hands-on experience is hard to fake and…
- Set controllable goals, such as publishing on a fixed cadence, rather than outcome goals like subscriber counts you cannot…
- Create external deadlines and accountability, such as promises to paying readers or a publisher, to overcome the procrastination…
Lenny’s Podcast99 min
Megan Cook · Feb 4, 2024
Key learnings- Pair product managers in small peer feedback groups every couple of weeks so people can share rough drafts and get feedback in a…
- Treat psychological safety as a precondition for bolder ideas; Megan argues the opposite of play is fear, not work.
- Schedule a recurring block for working through conflict early, so disagreements are addressed before they grow.
Lenny’s Podcast102 min
Emily Kramer · Sep 11, 2022
Key learnings- Think of marketing as fuel (the content, positioning and assets that add value) and engine (distribution, tracking and ops), then…
- Prioritize hiring for the business model, such as top-down sales versus product-led growth, over matching industry or audience…
- Your first marketer should ideally be a 'pie-shaped' generalist with deep expertise in one area, usually product marketing, plus…
Lenny’s Podcast98 min
Jason Shah · Sep 18, 2022
Key learnings- Reframe pushback as shifting direction toward shared goals: first identify what the other person actually cares about, then align…
- Use Amazon's working-backwards PR/FAQ: write the press release, customer quote, and leadership quote before building, forcing…
- Cut vague adjectives like 'great' and replace them with concrete numbers and specifics, since fewer, heavier words force sharper…
Lenny’s Podcast106 min
Arielle Jackson · Aug 18, 2022
Key learnings- Start with product positioning before anything else, since positioning drives most downstream marketing decisions; Arielle says…
- Run a structured naming process: write a naming brief, brainstorm hundreds of rough ideas, then screen candidates against…
- Prefer suggestive or evocative names that hint at what the company does, but accept that empty-vessel names like Eero can work if…
Lenny’s Podcast70 min
Upasna Gautam · Feb 23, 2023
Key learnings- Build buffer time into plans for newsroom work, since breaking news routinely pulls journalists away from scheduled research and…
- Use recurring touchpoints such as weekly demo days, multi-session working sessions, and office hours to gather continuous…
- Script breaking-news dress rehearsals to stress-test the platform under realistic time pressure before a real event hits.
Lenny’s Podcast87 min
Fareed Mosavat · Oct 23, 2022
Key learnings- Get better at product management by doing real work at real companies with real customers; courses, mentorship and reading only…
- Run an execute-generalize-communicate loop: ship work, extract transferable lessons such as when friction helps activation, then…
- Build sponsorship by doing excellent work and communicating it, so leaders who can open bigger opportunities notice you.
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 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…