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If you ever wanted to distill 3,310 hours of knowledge into 60 minutes, then this episode is for you. For the last 6 months, Lenny’s Podcast has been downloaded more than 2 million times and is now a top 10 technology podcast across both Apple and Spotify. And in this special episode, I’m breaking down the top 10 most downloaded episodes, plus sharing my favorite lessons from each. It's unlike anything I've done before, and I hope you love it. Happy holidays, happy new year, and from the bottom of my heart, thank you so much for listening, sharing, and for supporting the podcast. I’ll see you in 2023! — Find the full transcript here: https://www.lennyspodcast.com/countdown-of-the-top-10-episodes-of-the-year/#transcript — Thank you to our wonderful sponsors for supporting this podcast: • TED—ReThinking with Adam Grant: https://adamgrant.net/podcasts/rethinking/ • Notion—One workspace. Every team: https://www.notion.com/lennyspod • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — The 10 most downloaded episodes of 2022: 10. April Dunford on Lenny’s Podcast: https://www.lennyspodcast.com/april-dunford-on-product-positioning-segmentation-and-optimizing-your-sales-process/ 9. Crystal Widjaja on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-scrappily-hire-for-measure-and-unlock-growth-crystal-widjaja-gojek-and-kumu/ 8. Julie Zhuo on Lenny’s Podcast: https://www.lennyspodcast.com/julie-zhuo-on-accelerating-your-career-impostor-syndrome-writing-building-product-sense-using-intuition-vs-data-hiring-designers-and-moving-into-management/ 7. Shishir Mehrotra on Lenny’s Podcast: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/ 6. Kristen Berman on Lenny’s Podcast: https://www.lennyspodcast.com/using-behavioral-science-to-improve-your-product-kristen-berman-irrational-labs/ 5. Elena Verna on Lenny’s Podcast: https://www.lennyspodcast.com/elena-verna-on-how-b2b-growth-is-changing-product-led-growth-product-led-sales-why-you-should-go-freemium-not-trial-what-features-to-make-free-and-much-more/ 4. Ethan Smith on Lenny’s Podcast: https://www.lennyspodcast.com/the-ultimate-guide-to-seo-ethan-smith-graphite/ 3. Shreyas Doshi on Lenny’s Podcast: https://www.lennyspodcast.com/shreyas-doshi-on-pre-mortems-the-lno-framework-the-three-levels-of-product-work-why-most-execution-problems-are-strategy-problems-and-roi-vs-opportunity-cost-thinking/ 2. Marty Cagan on Lenny’s Podcast: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/ 1. Matt Mochary on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/ — In this episode, we cover: (00:00) About this episode (02:46) April Dunford on positioning your product (07:16) Crystal Widjaja on why most analytics efforts fail (11:42) Julie Zhuo on overcoming imposter syndrome (19:14) Shishir Mehrotra’s favorite interview question (23:27) Shishir Mehrotra’s PSHE career growth framework (27:10) Kristen Berman on using behavioral science to improve your product (33:29) Elena Verna on why retention is so important (36:31) Elena Verna on what to put into your freemium product (37:57) Ethan Smith on how people often under-resource SEO (38:46) Ethan Smith on when it’s time to invest in SEO (42:41) Shreyas Doshi’s LNO Framework (50:12) Marty Cagan on why big companies are often bad at product (51:46) Marty Cagan’s four steps to being a good product manager (53:48) Matt Mochary on the power of small teams (57:17) Matt Mochary’s advice for making hard conversations easier (59:05) Other episodes that left a lasting impact (59:40) Thank you for joining me (Lenny) on this incredible journey — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
Lenny introduces a special episode reflecting on the top 10 most popular episodes of his podcast. He shares the excitement of reaching over 2 million downloads and being recognized as a top technology podcast. This segment sets the stage for a countdown format, highlighting the unique approach of revisiting the most impactful discussions from the year.
"foreign y's podcast I'm Lenny and my goal here is to help you get better at the craft of building and growing products normally I interview world-class product leaders and growth experts to learn from..."
In this segment, Lenny introduces April Dunford, a leading expert on product positioning. April outlines the first crucial step in positioning: understanding competitive alternatives. She emphasizes the importance of recognizing both the status quo and other competitors, explaining how failing to address these can lead to losing deals. This foundational insight is vital for product managers and founders looking to effectively position their offerings.
"is to look back at the 10 most popular episodes that we've done so far so what I'm gonna do is count down from the 10th most popular episode to number one and play a Clipper two from that episode that..."
April Dunford elaborates on the concept of competitive alternatives in product positioning. She explains that many companies overlook the status quo, which often leads to losing deals to indecision. April stresses the need to identify what a product must compete against, including existing solutions and other shortlisted options. This segment provides actionable insights for product leaders on how to frame their positioning strategy effectively.
"welcome back and let's kick off this countdown with the 10th most popular episode of the Year and that is with April Dunford April is the author of obviously awesome she in my opinion is the smartest ..."
Lenny introduces Crystal Widjaja, who discusses the common pitfalls in analytics efforts within companies. Crystal shares her insights on why many analytics initiatives fail, emphasizing the need for actionable insights rather than mere data tracking. She provides practical advice on how teams can shift their approach to analytics to drive meaningful change and avoid the trap of treating data as entertainment.
"next up is Crystal wajia who's a long time Chief product officer at gojek she's currently Chief product officer at kumu and she's one of the smartest growth Minds that you probably have not heard of h..."
In this segment, Crystal Widjaja distinguishes between mere observations and actionable insights in data analytics. She uses relatable examples to illustrate how organizations often misinterpret data points without context. Crystal emphasizes the importance of deriving insights that can inform decision-making and drive real-world changes, making this a crucial lesson for data-driven teams.
"the eighth most popular episode of the year is our very first episode with Julie Zoo Julie was a long time design leader at Facebook she's now the founder of a company called Sundial she also wrote th..."
Lenny introduces Julie Zhuo, a former design leader at Facebook, who shares her personal journey with imposter syndrome. Julie reflects on her rapid career progression and the self-doubt she faced along the way. She offers valuable advice for early-career professionals on embracing discomfort as a catalyst for growth, making this segment an inspiring reminder of the challenges many face in their careers.
"deserve to be here do you really know what's happening you know you don't you're not really prepared for this job you've never done this before like what right do you have to be put in this situation ..."
Julie Zhuo discusses the duality of feeling like an imposter while simultaneously experiencing significant growth in her career. She encourages listeners to view uncomfortable situations as opportunities for learning and development. This segment highlights the importance of resilience and curiosity in overcoming self-doubt, providing a motivational perspective for anyone navigating their professional journey.
"it's amazing to hear that you had imposter syndrome for such a long period of time and you you basically ran design for like the Facebook app right yeah it's kind of an empowering inspiring Insight th..."
The speaker offers practical advice for dealing with imposter syndrome, including asking for help and seeking support from peers. They stress the significance of vulnerability in conversations and how it can lead to collaborative problem-solving and emotional support.
"something multiple times that you start to see the patterns you start to realize okay it's going to be all right and even you know now the people that I talk to the people I really look up to the peop..."
This segment focuses on the value of building a support network to navigate challenges in one's career. The speaker highlights how sharing struggles with others can lead to collective problem-solving and reassurance, ultimately helping individuals feel more confident in their abilities.
"asking for help now than I was earlier in my career you know I used to actually just try and hold it all in I was like hey I better fake it till I make it you know if no one thinks that I if everyone ..."
The speaker discusses how being open about challenges can strengthen relationships and foster collaboration. They emphasize that even leaders and founders benefit from sharing their difficulties, as it encourages teamwork and innovative solutions.
"because often that's just what you need you know you just need people to tell you it's going to be fine you're fine you're good you've got this and that you know that's so meaningful right whenever yo..."
In this brief segment, the speaker introduces Shishir Mehrotra, CEO of Coda and former VP of Product and Engineering at YouTube. They tease upcoming insights from Mehrotra, including his favorite interview question and career growth framework.
"answers sometimes by just sharing what the problem is by sharing the load L we're all going to collectively come up with with a better solution next up is shashir marotra CEO of Coda former vpa"
Shishir Mehrotra shares his favorite interview question, which involves a hypothetical scenario about a teleportation device. This segment highlights the importance of asking the right questions to uncover critical insights during interviews.
"shashir marotra CEO of Coda former vpa product and Engineering at YouTube If you have a Microsoft and here are two of my favorite clips from shashir one where he shares his favorite interview question..."
In this segment, Mehrotra discusses how to evaluate the viability of a product using two key questions. He illustrates how these questions can guide decision-making and strategic planning in product management.
"will start asking a bunch of questions and say well tell me more about this device like what does it do how does it work and you know is it is it big is it small is it fast does it like does it disint..."
Mehrotra emphasizes the value of low-stakes questions in learning and problem-solving. He shares how children excel at simplifying complex problems and how adults can benefit from adopting a similar mindset.
"two questions and he said like just with those two questions I can perform these quadrants you could say oh it's safe enough for humans and it's cheaper to they're very cheap to buy but expensive to r..."
This segment explores the evolving responsibilities of product managers as they advance in their careers. The speaker discusses how expectations shift from executing tasks to identifying problems and proposing solutions.
"way if you ask a kid that question the you know a new teleportation device you know you get to ask two questions almost every kid will like quickly get to two pretty good item questions again kids are..."
The speaker introduces the concept of PSHE (Problem-Solution-How-Execution) in product management. They explain how this framework helps evaluate performance and effectiveness in various roles within the tech industry.
"a problem we hand you a rough solution you figure out the help you figure out the how are we going to organize this what are the Milestones what you know how we're going to get to Market you know how ..."
In this segment, the speaker discusses the PSHE framework for evaluating talent and career growth. They explain how early career stages focus on execution, while later stages shift to evaluating how individuals approach problems. This framework is applicable not only to product management but also to other roles like sales, emphasizing the importance of understanding how to identify and solve problems effectively.
"interesting things that happened was that the teams went and they evaluated their teams on these two axes and there's they end up with a sort of curved line between them so it's not linear as you as y..."
Kristen Berman introduces the Three B's of behavior change, a model developed to help product managers and marketers understand user behavior. The first B emphasizes the importance of defining specific behaviors to change, while the second B focuses on reducing barriers to those behaviors. The third B highlights the need to create immediate benefits for users, ensuring they are motivated to take action today rather than procrastinating.
"is with Kristen Berman founder of irrational Labs on using Behavioral Science to improve your product here is Kristen describing the Three B's of Behavior change there are so so many mistakes that hum..."
In this segment, the speaker elaborates on the barriers that prevent users from taking desired actions. They differentiate between logistical barriers, such as technical difficulties, and cognitive barriers, like uncertainty and status quo bias. By addressing these barriers, product managers can enhance user engagement and drive behavior change effectively.
"to open up Uber and say like maybe it'll come faster and so when there is uncertainty in our life we either look for other options or we just don't make a decision at all right this is by the way very..."
The discussion continues with the third B of behavior change, focusing on the importance of providing immediate benefits to users. The speaker explains how present bias affects decision-making and emphasizes the need for product features that offer instant gratification, such as completion notifications, to encourage user engagement and retention.
"definitely have completion bias I love checking those freaking check boxes this episode is brought to you by vanta helping you streamline your security compliance to accelerate growth if your business..."
Elena Verna shares insights on the critical role of product-led retention in driving growth. She explains that successful acquisition strategies depend on a strong foundation of user retention, activation, and engagement. Verna emphasizes the need for products to create habitual usage patterns to facilitate organic growth and user referrals.
"activation and engagement then you can choose is your product has a relationship of one to many if it has a collaboration at its core say slack or Miro or even the amplitude or does it have a more of ..."
In this segment, Verna discusses how to approach freemium models strategically. She outlines key considerations for determining which features to offer for free, emphasizing the importance of aligning free offerings with growth objectives without compromising monetization potential. This framework helps product leaders make informed decisions about their freemium strategies.
"it for a product leader or founder who's thinking about what they should make free in their freemium model do you have kind of a mental model of how you think about here's what you should make free or..."
Ethan Smith shares valuable insights on the often-overlooked importance of SEO in driving traffic and growth. He critiques the tendency of companies to underinvest in SEO while over-relying on paid advertising. Smith emphasizes the need for a robust SEO strategy to complement marketing efforts and maximize visibility.
"each other so you can kind of mix and match them in order but at this point the fourth most popular episode of the year is with Ethan Smith CEO of graphite and just general SEO Guru here are two clips..."
In this segment, Ethan Smith explains how to assess whether SEO can be a growth driver for a business. He identifies two critical factors: the size of the addressable market and the authority of the company. By analyzing traffic data and referring domains, businesses can determine their potential for SEO success and strategize accordingly.
"first thing is is the addressable market large so is the addressable market for SEO large and for most categories it is the second is do you have authority do you have existing traction if you start f..."
Ethan Smith elaborates on the concept of addressable market in relation to SEO. He discusses how to evaluate the potential market size for a product and the importance of targeting the right personas. This segment provides insights into how to create effective content strategies that align with market demands.
"Market that's a little bit more complicated but most markets are pretty large actually in SEO but we want it to be large so with powers and actually an interesting example so they're a clinical trial ..."
Shreyas Doshi introduces the LNO framework, which categorizes tasks into leverage, neutral, and overhead tasks. He shares his personal experience of feeling overwhelmed as a new product manager and how this framework helped him prioritize effectively. This segment is valuable for anyone looking to enhance productivity and focus on high-impact tasks.
"there are product competitors and audience competitors so for something like uh I'm at a wework right now so for wework I could look at the traffic for other you know rental office companies or I coul..."
In this segment, Shreyas Doshi emphasizes the importance of identifying and focusing on leverage tasks (L tasks) that yield the highest impact. He shares strategies for managing time effectively by reducing effort on neutral and overhead tasks. This approach can significantly enhance productivity for product managers and professionals in high-leverage roles.
"Twitter and now he has his own course on Maven here is shreyas describing the LNO framework which people have brought up so many times after this episode and that I've personally found incredibly usef..."
Shreyas Doshi discusses how different tasks can vary in their impact and how to prioritize them accordingly. He provides examples of common tasks, such as filing bug reports and taking notes, illustrating how they can be classified as L, N, or O tasks based on context. This segment offers practical advice for improving task management and efficiency.
"so again very stressful time in my career and then things changed when I discovered the ideas related to this LNO framework in a blog post and I can't unfortunately I can't even find that blog post so..."
In this segment, Shreyas Doshi highlights the significance of context when managing tasks. He explains how the same activity can be treated differently based on its importance and the desired outcome. This insight is crucial for professionals aiming to optimize their workflow and ensure that their efforts align with strategic goals.
"they by default treat each of these types of tasks the same way and therein lies the problem so this was the Epiphany for me back at Google when I kind of discovered some of these ideas and what I rea..."
Shreyas Doshi shares his approach to note-taking, emphasizing the need to tailor the depth and detail of notes based on the context of the meeting. He contrasts the need for thorough notes in high-stakes discussions with the efficiency required in routine meetings. This segment provides actionable tips for improving communication and documentation practices.
"and so there are some tasks that you do a classic example of an O task is say an expense report right like it sounds silly but I used to try to make my expense reports really good wow and and sometime..."
In this segment, Shreyas Doshi discusses the importance of clarity and precision in communication, especially in high-stakes situations. He explains how to refine notes and reports to ensure that key decisions are clearly articulated, preventing misunderstandings. This advice is essential for product managers and leaders aiming to enhance their influence and effectiveness.
"last example I'll use to illustrate this is taking notes it turns out even taking notes taking not synthesizing them and then sharing them can actually be an L task an end task or an O task depending ..."
Marty Cagan shares his insights on why larger companies often struggle with product management. He discusses the shift in focus from product innovation to sales and marketing as companies grow, leading to a decline in product importance. This segment provides a critical perspective on the challenges faced by product managers in established organizations.
"helps illustrate the some of the ideas behind the LNO framework runner-up for the most popular episode of the year is my conversation with Marty Kagan Marty is the Legend of Legend of product managers..."
In this segment, Marty Cagan outlines four essential steps for becoming a successful product manager. He emphasizes the need for preparation and contribution to the team, providing a roadmap for aspiring product leaders. This practical guidance is invaluable for anyone looking to excel in product management.
"problem but let's just say there's a product manager and nobody's ever coached this poor person and so they really don't know much so the first thing that product manager needs to do is get themselves..."
Lenny introduces Matt Mochary, a CEO coach, and discusses the advantages of small teams in achieving higher productivity. This segment highlights Mochary's insights on how smaller teams can outperform larger ones in delivering results.
"product manager that is the single biggest area empowered teams fall down the product manager is ill-equipped or a nice way of saying incompetent and finally our number one most downloaded most popula..."
Mochary shares experiences from the early days of the pandemic, discussing how companies had to make tough decisions regarding layoffs. This segment reveals surprising outcomes where companies operated more efficiently post-layoff, challenging conventional wisdom about workforce size.
"coach he's worked with CEOs of companies like open AI coinbase notion Rippling angelist so many other amazing folks that I could just keep listing in this episode there are just so many nuggets of wis..."
In this segment, Mochary explains how adding more employees can lead to increased overhead and coordination issues. He discusses the importance of maintaining a lean team to enhance communication and morale, drawing on examples from successful companies.
"and so almost every one of my companies did some on the low side of five percent some on the high side of one company that was is a hotel company um Let Go 40 because it looks like their business was ..."
Mochary shares his approach to conducting difficult conversations, emphasizing the importance of preparing the other person for the discussion. This segment provides valuable strategies for delivering tough news while minimizing emotional distress.
"grows and grows and really the only answer is I mean that's why people bring me it because they're growing growing growing and things are breaking so I have a system that keeps things together but it ..."
Lenny wraps up the episode by reflecting on the journey of the podcast over the past year. He expresses gratitude to listeners and sponsors, while also inviting feedback to improve future episodes. This segment encapsulates the essence of growth and community in podcasting.
"in it so that's the first thing I do this is going to be a difficult conversation are you ready person says yes then I share the news I'm letting you go here's why that then the second so that I give ..."
In the closing segment, Lenny shares his vision for the future of the podcast, promising more engaging topics and expert guests. He encourages listeners to continue their journey of learning and invites them to share their thoughts on the podcast's direction.
"same more amazing guests more topics that maybe you haven't thought about that you need help with maybe more amazing topics that you know you need help with that I want to help you solve I'm still lea..."