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4 questions Shreyas wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google
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Shreyas Doshi is a former product leader at Stripe, Twitter, Google, and Yahoo. He’s now a full-time advisor and coach to founders and executives. Shreyas is known for his incredibly insightful writing on products, which has garnered him a passionate following in the PM and startup community. Last week, we sat down together at the very first Lenny and Friends Summit in San Francisco for a special live episode. We covered: • Why product leaders often feel overwhelmed with work, and how to combat it • The importance of developing good taste, and how to do it • How to reduce frustration in your product leadership role • The critical skill of truly listening as a leader • Common pitfalls in annual planning and decision-making • Lots of laughs To learn more from Shreyas, check out these courses: • Improving Your Product Sense: https://bit.ly/product-sense • Managing Your PM Career: https://bit.ly/pm-career-course — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny • Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript at: https://www.lennysnewsletter.com/p/shreyas-doshi-live Where to find Shreyas Doshi: • X: https://x.com/shreyas • LinkedIn: https://www.linkedin.com/in/shreyasdoshi/ • Threads: https://www.threads.net/@shreyas.threads • Linktree: https://linktr.ee/shreyasdoshi • YouTube: https://www.youtube.com/@ShreyasDoshiVideos Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction (5:35) Question one: Why am I so busy? (10:08) Annual planning as an example (16:48) Tactical tips for staying less busy (25:20) Question two: Do I actually have good taste? (38:09) Question three: Why does my job feel so frustrating? (43:29) Question four: Am I really listening? (44:35) Closing remarks Referenced: • 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: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi • LNO framework: https://twitter.com/shreyas/status/1492345184171945984 • Time management techniques that actually work: https://www.lennysnewsletter.com/p/time-management-techniques-that-actually • Part 2: Time management techniques that actually work: https://www.lennysnewsletter.com/p/part-2-time-management-techniques • Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720 • Stripe Connect: https://stripe.com/connect • Jeff Bezos explains one-way door decisions and two-way door decisions: https://www.youtube.com/watch?v=rxsdOQa_QkM • Spotify Is America’s Most Loved Workplace: https://www.newsweek.com/2021/10/29/spotify-americas-most-loved-workplace-1639982.html • Shreyas on “thinking is cheap”: https://www.linkedin.com/posts/shreyasdoshi_thinking-is-very-cheap-doing-is-very-expensive-activity-7225237421813116929-Qzi3/ • Good Product Strategy, Bad Product Strategy from Shreyas: https://x.com/shreyas/status/1244810075908128768 • Shreyas on annual planning and metrics: https://x.com/shreyas/status/1302423854095036421 https://x.com/shreyas/status/1304628719374544896 • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/ • Patrick Mahomes’s website: https://www.adidas.com/us/patrick_mahomes • Virat Kohli: https://en.wikipedia.org/wiki/Virat_Kohli • Reversible and Irreversible Decisions: https://fs.blog/reversible-irreversible-decisions/ • Fail fast: https://en.wikipedia.org/wiki/Fail_fast • 3 levels of product work: https://twitter.com/shreyas/status/1370248637842812936 • Shakespeare quote: https://nosweatshakespeare.com/quotes/famous/to-thine-own-self-be-true/ • Rick Rubin: Legendary Music Producer | Lex Fridman Podcast #275: https://www.youtube.com/watch?v=H_szemxPcTI • Blake Burge on Rick Ruben: https://x.com/blakeaburge/status/1794470295828341222 • Rick Rubin on X: https://x.com/RickRubin • Dee Hock on X: https://x.com/deewhock • Dee Hock quote on listening: https://x.com/shreyas/status/1351279398423465984 • Peter Drucker: https://en.wikipedia.org/wiki/Peter_Drucker • Peter Drucker quotes on listening: https://www.azquotes.com/author/4147-Peter_Drucker/tag/listening • Lenny’s first podcast recording: https://www.youtube.com/watch?v=YP_QghPLG-8 • A Recipe to Become a Great Listener: https://www.youtube.com/watch?v=gUQJkiDy2Ko Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Segments Timeline
Welcome to the Lenny and Friends Summit
In this exciting introduction, Lenny welcomes Shreyas Doshi to the podcast, highlighting his previous appearance as one of the most popular episodes. Shreyas shares his enthusiasm for the live format and reflects on the unique venue, setting the stage for a discussion on critical questions he wishes he had asked himself earlier in his career as a product leader.
"today I am super excited to bring you a very special episode with Shas Doshi recorded live at the lenan friend Summit in front of a thousand people in San Francisco this is shas's second time in the p..."
Reflecting on Career Questions
Shreyas Doshi discusses the importance of self-reflection in his career as a product manager. He shares that despite his success, he faced significant challenges and stresses, leading him to realize there are key questions he wished he had asked himself sooner. This segment sets the tone for the insightful questions that will follow.
"I bring you shos Doshi shos thank you so much for being here and welcome to the podcast thanks Lenny for having me this is amazing I was going to ask what do you uh we recorded our first episode I thi..."
The Burden of Busyness
Shreyas dives into the first question he wished he had asked himself: 'Why am I so busy?' He reflects on his years of feeling overwhelmed and stressed as a product leader, emphasizing that despite working hard, he often felt dissatisfied. This segment highlights the common struggle of busyness in the product management field.
"used for uh Jimmy Hendrick performed here and artha Franklin performed here so we're it's like Jimmy Hendrick ARA Franklin Shas there we go that's going up on my Twitter by soon okay so so usually whe..."
Understanding the Source of Stress
In this segment, Shreyas elaborates on the reasons behind his constant busyness and stress during his career. He shares personal anecdotes about how this stress manifested physically, illustrating the toll that a demanding product management role can take on one's health and well-being.
"years there are some questions I wish I had asked myself sooner but I did not um and I had the great luck of having a life a PM life full of suffering um and I have zero complaints about it uh but as ..."
The Illusion of Productivity
Shreyas discusses the paradox of productivity in product management. He acknowledges that while there are many tips and techniques to manage time effectively, the reality is that as one's scope of work increases, so does the busyness. This segment challenges the notion that productivity hacks can solve the underlying issues of workload.
"some point your customers will start asking for Enterprise features like samle authentication and skim provisioning that's where work OS comes in making it fast and painless to add Enterprise features..."
Annual Planning and Its Challenges
Shreyas reflects on the annual planning process that often contributes to overwhelming busyness. He describes the typical chaos of planning season, filled with spreadsheets and meetings, and how it can lead to feelings of guilt and stress. This segment emphasizes the need for a more effective approach to planning in product management.
"flexible model that can be adapted to even the most complex use cases if you're currently looking to build role-based access control or other Enterprise features like single sign on skim or user manag..."
Breaking the Cycle of Overwhelm
In this segment, Shreyas shares his realization that the traditional approach to annual planning doesn't have to consume weeks of time. He discusses how he learned to streamline the process, ultimately leading to a more manageable workload and less stress. This insight is crucial for product leaders seeking to improve their planning efficiency.
"engineering teams at copy ai ai 21 and over 100 other B2B SAS companies use Paragon so they can focus their efforts on core product features not Integrations the result they've shipped Integrations se..."
The Reality of Execution
Shreyas highlights the disconnect between planning and execution in product management. He explains how, despite spending significant time on planning, teams often end up deviating from the original plan due to unforeseen customer needs and escalations. This segment underscores the importance of adaptability in product leadership.
"background is that like you know I have spent most of my career just being completely stressed out just absolutely stressed T out every day uh and there were many reasons for it but one of the core re..."
Plans vs. Planning
Shreyas concludes this segment by discussing the famous adage that 'plans are useless, but planning is everything.' He reflects on how this perspective can help product leaders navigate the complexities of their roles and maintain focus on what truly matters. This insight is vital for anyone involved in product management.
"leader and it's only so I I I did like the product I did product work for about 20 years before I started this new chapter of my career and I think I only fixed it in the last three or four years of m..."
Why Am I So Busy?
Shreyas Doshi reflects on the overwhelming busyness that product leaders often experience, particularly during planning seasons. He shares his realization that despite managing his time efficiently, the lengthy planning rituals at Stripe led to unnecessary stress. This segment emphasizes the importance of questioning the status quo in planning processes and finding more efficient ways to approach product strategy.
"to change that at some point and uh actually found a solution again late in my career but I found a solution because I asked myself this question which is why am I so busy I'm doing all the efficiency..."
The Illusion of Planning
In this segment, Shreyas discusses the common pitfalls of annual planning, highlighting how teams often forget the plans they meticulously crafted. He quotes the saying, 'Plans are useless, but planning is everything,' to illustrate the disconnect between planning and execution. This insight encourages product leaders to focus on the planning process itself rather than getting bogged down by rigid plans.
"lot of excitement and January goes fine until you get three customer escalations for features that were not in your plan right and so now you try to figure out how you going to revise resources you go..."
Bending the Rules of Planning
Shreyas shares a pivotal moment in his career when he realized that having a clear product strategy could drastically reduce the time spent on planning. He recounts how he was able to complete a major product strategy in just three days, compared to the typical four to six weeks. This segment emphasizes the value of having a well-aligned product strategy to streamline planning and execution.
"so I went through a few years of this and then I go you know what I'm going to bend some rules here and so what I realized Lenny is um you don't have to go through these four to six weeks and it was a..."
Tactical Tips for Less Busyness
In this segment, Shreyas offers tactical advice for product leaders to combat busyness. He suggests that having a clear strategy can alleviate many prioritization and planning challenges. Shreyas encourages leaders to focus on strategic decisions rather than getting lost in the minutiae of roadmaps, advocating for a more streamlined approach to product management.
"planning actually goes away now you still have to do some resource allocation and all of that but even there you don't need that false precision like how many of you have gotten into arguments about s..."
The Cost of Poor Product Decisions
Shreyas discusses the consequences of making hasty product decisions without thorough consideration. He illustrates how product teams often rush into building features based on superficial assessments, leading to wasted resources and unmet customer needs. This segment serves as a cautionary tale about the importance of thoughtful decision-making in product management.
"basically versus like every single person and their road map for the next six months like what's the piece of advice to each other and then I want to move on to the next question because I want to mak..."
Understanding One-Way vs. Two-Way Doors
In this insightful segment, Shreyas explains the difference between one-way and two-way doors in decision-making. He emphasizes that many decisions perceived as reversible are actually one-way doors for product managers, leading to increased busyness and stress. Shreyas encourages leaders to take time to reflect before making decisions, highlighting the importance of understanding the implications of their choices.
"decisions as I can uh so can I share an example of pleas uh so what I noticed is that um you know you have a meeting about some product feature uh that somehow is requested or is really important what..."
Talk is Cheap: The Value of Thoughtful Action
Shreyas reflects on the culture of execution over strategy in tech companies, sharing insights on how to prioritize thoughtful decision-making over mere action. He emphasizes that while execution is crucial, having a clear strategy is equally important for product success.
"compliance for sock 2 ISO 270001 Hippa and more with a single platform vanta V's Market leading trust management platform helps you continuously monitor compliance alongside reporting and tracking ris..."
Do I Actually Have Good Taste?
Shreyas poses a critical question about taste in product management, recounting his journey from believing execution was everything to recognizing the necessity of a solid product strategy. He shares personal anecdotes from his time at Google and Twitter that shaped his understanding of taste in product leadership.
"v.com Lenny I I know it's Spotify I heard one of their core values is talk is cheap but it's the virtue version of that it's like they actually prefer to talk more and I think that's exactly what you'..."
The Folly of Ignoring Strategy
In this segment, Shreyas reflects on his early career misconceptions about strategy, particularly during his time at Google. He discusses how he learned the hard way that a lack of product strategy can hinder a company's potential, using Twitter's struggles as a case study.
"this question after again all of these things by the way everything I say I have been that guy I've made that mistake right so that's why like I just have to admit to myself that yes I've made these m..."
Recognizing the Need for Product Strategy
Shreyas elaborates on the importance of having a cohesive product strategy, sharing insights from his experiences at Twitter and Stripe. He emphasizes that taste is not just about aesthetics but also about the beliefs and decisions that guide product development.
"even remember there were not that many PMS but there was a PM at uh Google who was kind of like the same level as me but he like just had much more wisdom than me and he was trying to nudge me into li..."
Taste Beyond Aesthetics
Shreyas dives deeper into the concept of taste, explaining how it influences product leadership decisions. He stresses the need for product leaders to cultivate good taste in their beliefs and learning sources, which ultimately shapes their decision-making and leadership style.
"Folly right of like oh wait a minute I spent like I was at Google 6 years I spent like most of those six years kind of saying like ah strategy is useless there's no point to strategy execution is wher..."
Evaluating Ideas Beyond Social Proof
In this segment, Shreyas discusses the importance of evaluating ideas independently of their social proof or authority. He shares insights on how to become a rigorous thinker by shedding preconceived notions and biases that can cloud judgment in product management.
"talking about when I say do I really have good taste and when I asked myself this question and again I had to be like it like I really had to dig deep it wasn't easy but at some point I realized that ..."
The Power of Metaphors in Decision-Making
Shreyas Doshi discusses the allure of catchy metaphors in decision-making frameworks, such as 'one-way door' and 'two-way door' decisions. He reflects on how these terms can overshadow more complex ideas like reversible and irreversible decisions, emphasizing the importance of critical thinking over catchy phrases.
"a few observations if I might so like the first one is we get overly excited about cool metaphors okay like one way door Two Way doors right there's some guy I don't know who it is I just read somewhe..."
The Allure of Alliteration
In this segment, Shreyas critiques the tendency to favor alliterative phrases like 'fail fast' over more straightforward alternatives. He questions whether the appeal of such phrases influences our understanding and acceptance of concepts in product management.
"get very impressed with um alliterations I'm serious we get very impressed with alliterations okay so uh how many of us love fail fast fail fast okay nobody's going to raise hands now okay fine maybe ..."
Shedding Social Proof for Critical Thinking
Shreyas shares his journey towards becoming a more critical thinker by shedding reliance on social proof and authority bias. He emphasizes the importance of evaluating ideas on their own merit, which has significantly impacted his growth as a product leader.
"um we also get very impressed with complicated charts and math we don't understand and some of you product leaders who are at the top of the game you actually use this as a strategy right so so as I r..."
Understanding Job Frustrations
Shreyas reflects on the frustrations he faced in his product management leadership role, attributing them to a misalignment with his core strengths. He introduces a framework for understanding product work at three levels: impact, execution, and optics, and discusses how operating outside one's preferred level can lead to dissatisfaction.
"thinker I want to move on to the next question just so we can get through some of these questions before I do can you just show people your notes real quick just like show it like from a distance this..."
Identifying Your Superpowers
In this insightful segment, Shreyas encourages product leaders to identify their superpowers and align their work with them. He shares his personal experience of stepping back from traditional corporate paths to find fulfillment in earlier-stage product environments, advocating for authenticity in career decisions.
"that there's also you know uh what I what I learned at the time when I started asking this question is that our jobs get frustrating when we behave most of the time in misalignment with our superpower..."
The Art of True Listening
Shreyas poses the critical question of whether we are truly listening in our roles as leaders. He highlights the deeper levels of listening that can transform leadership effectiveness and recommends resources from thought leaders like Rick Rubin and Peter Drucker to enhance listening skills.
"like as you go you know as you go higher up in the corporate ladder no matter what kind of company it is you are now going to have to spend a lot of time on Optics at the Optics level and I have willp..."
Closing Thoughts and Reflections
As the discussion wraps up, Shreyas shares his final thoughts on the importance of self-awareness and authenticity in leadership. He invites the audience to reflect on their own listening skills and the impact of their decisions, leaving them with a call to action for personal growth.
"and you won't have that frustration I wish we had an hour for every single one of these questions I feel like there's so much more to get into we have 40 seconds do you want to touch on your last ques..."