Shreyas Doshi, a former product leader at Stripe, Twitter, and Google, now guides founders as an advisor and coach. He discusses the overwhelm often felt by product leaders and how to combat it. Shreyas emphasizes the need for developing good taste and effective listening skills to enhance leadership. He shares insights on avoiding common pitfalls in annual planning, stressing the importance of a clear product strategy. The conversation is both informative and filled with relatable humor, offering valuable advice for aspiring product managers.

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:* April Dunford on Lenny’s Podcast: https://www.lennyspodcast.com/april-dunford-on-product-positioning-segmentation-and-optimizing-your-sales-process/* Crystal Widjaja on Lenny’s Podcast: https://www.lennyspodcast.com/how-to-scrappily-hire-for-measure-and-unlock-growth-crystal-widjaja-gojek-and-kumu/* 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/* Shishir Mehrotra on Lenny’s Podcast: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/* Kristen Berman on Lenny’s Podcast: https://www.lennyspodcast.com/using-behavioral-science-to-improve-your-product-kristen-berman-irrational-labs/* 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/* Ethan Smith on Lenny’s Podcast: https://www.lennyspodcast.com/the-ultimate-guide-to-seo-ethan-smith-graphite/* 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/* Marty Cagan on Lenny’s Podcast: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/* 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. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

#5: Welcome back to the Skip podcast! In this episode, Nikhyl invites Shreyas Doshi to discuss the ever-evolving role that Product managers have in today's business world, finding yourself “stuck” in the ‘middle-stage’ of your career and how making high-quality career decisions is more important than ever. Using more than a decade of experience, Shreyas also describes vastly different experiences in similar roles at similar (or sometimes very different) companies, following your own internal excitement to help guide you in the proper direction, and how to optimally manage the critical transition from an operator role into an advisory role.Shreyas Doshi has led & scaled products at Stripe, Twitter, Google, and Yahoo in over 15 years as a product manager & PM leader. In this next chapter of his career, he is an advisor for fast-growing startups across the globe and is building out content & courses based on his experience of building successful products & teams across various domains. Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookShreyas Doshi: LinkedIn | Twitter | Website Full Show Notes:[1:00] Welcome to The Skip![2:00] Introducing our guest Shreyas Doshi[3:00] “Careers are made by not one playbook, but having many playbooks. Every new challenge is not a page out of a previous playbook, but it's a blend of all these different lessons that one's learned.“ - Nikhyl Singhal[4:00] Sheryas’ experience as PM at Stripe, and redefining the idea of Product Management[9:00] “Trying to put product management as a role in a spreadsheet with cells and specific rules doesn't quite work in my opinion.” - Shreyas Doshi[10:00] How different companies and different company cultures impact the role of Product Managers[14:30] In the 'Act Two’ of your career, how do you best shift to an advisory role?[20:00] It can be useful to follow the emotional excitement about particular opportunities, and using that to gain momentum that eventually leads you to the right opportunity down the road[22:30] Quality Questions as a Superpower… The efficacy of your role as an advisor likely depends largely on the quality of the questions you ask.[24:00] Nudge, nudge: Follow Shreyas on Twitter[25:00] Sheryas’ sought his own advisors to figure out what’s next, and the answer was building effective courses[28:00] “My hypothesis was that if I structure this in a unique way and if I treat this course, like I would treat a product and kind of basically just like product manage it, since that I can have the right kind of effect on my users, in this case, my students, then that would be a wonderful kind of experience and hopefully useful for students. And that hypothesis, I would say, has been proven at this point because a lot of people have told me that it substantially changed the way they were thinking about their career.” - Shreyas Doshi[32:00] Discussing Shreyas’ tweet on success in academics vs. professional life[36:00] One's career may reach a point where they feel like they are no longer advancing or growing, which is commonly known as career plateauing, and this stage often causes a great deal of frustration[42:30] The difficulties of going from a large company with many layers of structure to a startup with essentially no multi-domain structure[44:00] Eric Wienstein’s “High Agency”[48:00] “Especially as leaders, most of our problems are actually in many ways messaging problems - because we know what the right thing is, and how we got to that conclusion, but there are so many challenges along the way to kind of message it in a way that resonates with everybody.” -Shreyas Doshi[51:00] It is important to keep in mind that both internal and organizational changes require a significant amount of time[52:00] For individuals who feel like they are at a standstill in their career, Shreyas offers advice on how to move forward.[53:00] Be rigorous about your career decisions. Take pride in your career.[1:00:00] Find Shreyas on Twitter and Linkedin!—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.Join entrepreneur, coach, and Facebook VP Nikhyl Singhal as he offers guidance on navigating important career decisions, management challenges, and personal crossroads. For many, career is one of the most critical parts of identity. Yet most people don’t have a clear sense of how to maximize their current position, evaluate job transitions, or invest in the right long-term skills to optimize their professional life. Unfortunately, if you work at a company, your manager is rarely capable or incentivized to help you develop the necessary skills or to think through transitions. And most self-help books and articles focus on your current role, not on the next one or on any sort of long-term career roadmap.Nikhyl advises nearly a hundred leaders on their tech careers. Nikhyl is certain, however, there are many others also looking to become more intentional about their career choices – which has led him to produce this podcast. Each edition, Nikhyl will dive into some of the common questions he encounters and give his distinctive insight with the hope of reaching as many people as possible. Though Nikhyl mostly works with tech leaders, he believes the themes apply to anyone looking to shape a fulfilling career.

This podcast with Shreyas Doshi, the most followed product leader in the world, we cover a range of topics on Successful Product Teams, Products and Careers. Listen in to hear: Why the most successful product companies still launch failed products. Why you need courage to be able to build products that are going to be successful. How AI is going to impact your Product Management career. 

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped define and grow the Product Management function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter and prior to Twitter spent over 6 years as a Group Product Manager @ Google. Today Shreyas has invested and advises some of the best including advising Airtable, Kalshi, Lendflow, to name a few. In Today's Episode with Shreyas Doshi: 1.) Entry into Product: How did Shreyas make his way into the world of product and product management? Why did Shreyas decide not to do business school when it was the conventional route for everyone going into product management? What were some of Shreyas' biggest takeaways from his time at Stripe and Google? How did they impact his product mind today? 2.) Product Management 101: How does Shreyas define product management today? How do many confuse it? How does Shreyas define product success today? What is the single biggest mistake Shreyas sees founders make when determining the success/PMF of their product? Does Shreyas believe that great product management is science or art? Data or intuition? When should you listen to customers? When should you not? 3.) Metrics 101 & How To Use Them: What is the single biggest mistake Shreyas sees founders make when it comes to selecting their North Star metric? How should founders think about input vs output metrics? What is the difference between the two? What are the 6 types of metrics that all founders and product teams need to focus on? How does their importance change over time? How should the responsibility for these metrics be split between different people and teams? 4.) Three Types of Product Leader: What are the three different types of product leaders? The Craftsperson: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company? The Operator: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company? The Visionary: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company?

In this conversation, Shreyas Doshi, a product and leadership expert with an impressive background at Stripe, Twitter, Google, and Yahoo, delves into the intriguing concept of 'founder mode.' He explains it as a mindset crucial for early-stage startups, emphasizing its appeal and complexities. Shreyas discusses the balance between detail-oriented management and broader strategy, the confidence founders need in their product vision, and the operational insights from his rich experience. His profound insights shed light on navigating leadership dynamics effectively.

Shreyas Doshi is a startup advisor who has formerly worked in the product teams of tech firms like Stripe, Twitter, Google, Yahoo. He regularly writes about product, strategy, org psychology, leadership, and life! Important Links: Twitter: https://twitter.com/shreyas LinkedIn: https://www.linkedin.com/in/shreyasdoshi Show Notes: Shreyas’s childhood Operating with the owner mindset The LNO framework Getting good at leveraging time The antithesis principle Having a great manager Individual vs. group decision making “Apple Pie” positions Beware of certainty theater Social media: A global intelligence network Minimizing your opportunity costs The issue with following the rubric Lessons from school at the workplace Learning to unlearn Tao Te Ching on leadership Being an invisible leader Tight vs. weak grip And MUCH more! Books Mentioned: The Science of Storytelling; by Will Storr The Status Game; by Will Storr Tao Te Ching; by Lao Tzu

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org.  Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products.  Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack.  For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

Shreyas Doshi, a former product lead at tech giants like Stripe and Google, shares powerful insights with Kunal Shah. They discuss the art of product thinking, balancing talent with hard work, and the risks of being overly data-driven. Shreyas emphasizes the importance of qualitative judgement over pure metrics, the traits that differentiate exceptional product thinkers, and the value of authentic leadership. He also reflects on the role of childhood experiences in shaping product sense and the founders' impact on company culture.

Experienced product leader Shreyas Doshi shares insights on time management, online teaching success, writing benefits, brilliance curse, luck vs. talent, stack ranking for prioritization, and using mental simulations for decision-making.