4 questions Shreyas wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google

Introduction (0s)

• A special episode featuring Shreyas Doshi was recorded live at the Lenan Friend Summit in San Francisco, attended by a thousand people. (2s)
• This is Shreyas Doshi's second appearance on the podcast, with his first episode being the third most popular of all time. (10s)
• The discussion includes three main questions and a bonus question that Shreyas wished he had asked himself earlier in his career. (19s)
• Topics covered include the busyness and frustrations of product leaders, the importance of developing good taste, and the need for better listening skills. (26s)
• The episode was recorded in a venue that was previously a car dealership and has hosted performances by Jimi Hendrix and Aretha Franklin. (1m27s)
• Shreyas reflects on his career as a product management leader, expressing a desire to have been more honest with himself about certain questions earlier in his career. (2m21s)

Question one: Why am I so busy? (5m35s)

• The question "Why am I so busy?" is explored, highlighting a career spent in constant stress due to being perpetually busy, which led to dissatisfaction despite hard work. (5m43s)
• Over a 20-year career in product management, the issue of being overly busy was only resolved in the last few years, leaving about 16 or 17 years of stress and health issues related to this busyness. (6m44s)
• The discussion acknowledges that many people feel overwhelmed by their workload, as indicated by a show of hands from the audience. (7m33s)
• Common productivity tips and techniques, such as maintaining a to-do list and using frameworks like the LNO framework, are mentioned, but they are not sufficient to manage the overwhelming scope of responsibilities that come with career growth. (8m2s)
• As one's career progresses, the scope of responsibilities increases to a point where no amount of efficiency or prioritization can prevent being extremely busy, a challenge faced for many years before finding solutions. (9m30s)
• The conversation suggests that while productivity tricks are popular, they are not a long-term solution, and a different approach is needed to address the issue of being perpetually busy. (10m3s)

Annual planning as an example (10m8s)

• During annual planning, high-level managers often find themselves overwhelmed with tasks such as filling out spreadsheets, attending meetings, managing dependencies, setting priorities, and coordinating with stakeholders. This process can take up to two or three months, leading to feelings of busyness and guilt due to other responsibilities being neglected. (10m10s)
• Despite being efficient with time management, such as maintaining a well-organized to-do list and calendar, the speaker realized that the planning season itself was a significant contributor to their busyness. This realization occurred during their time at Stripe. (11m48s)
• The planning process typically involves creating detailed plans over four to six weeks, presenting them to executives, and starting the new year with enthusiasm. However, unexpected customer escalations often require revising these plans, leading to a situation where the original plan is forgotten by the end of February. (12m50s)
• There is a common saying that "plans are useless, but planning is everything," which is often quoted in such situations. However, the meaning of this phrase is not well understood, and it is frequently used to justify the planning process despite its inefficiencies. (13m42s)
• After experiencing this cycle for several years, the speaker decided to bend some rules to address the inefficiencies in the planning process. (14m8s)
• A well-defined and aligned product strategy can significantly reduce the time required for planning, as demonstrated by the experience with Stripe Connect, where planning was completed in just three days compared to the usual four to six weeks. (14m16s)
• Having a genuine product strategy that everyone agrees on can eliminate unnecessary tasks and streamline the annual planning process, reducing the need for filling out irrelevant templates. (14m50s)
• The focus should be on high-leverage activities rather than spending excessive time on tasks perceived as strategic, such as debating precise resource allocations that are unlikely to be adhered to in the future. (15m58s)
• Although creating a clear product strategy requires upfront effort, it simplifies subsequent planning and ensures that everyone is on the same page, making the process more efficient. (16m35s)

Tactical tips for staying less busy (16m48s)

• A strategic approach can alleviate many prioritization and planning issues, providing a framework to handle escalations from sales or support effectively. (17m20s)
• Being overly busy can result from not making optimal product decisions, even for experienced product managers. (17m52s)
• In product meetings, decisions are often made hastily without thoroughly considering customer motivation, differentiation, and distribution strategies. (18m34s)
• The common practice of making quick decisions based on the idea of "two-way doors" can lead to inadequate product development processes. (19m10s)
• In reality, committing to a feature often involves a significant time investment, contrary to the belief that it can be easily reversed. (20m31s)
• During a quarterly business review (QBR), a product manager may face challenges when a newly launched feature has not gained much adoption. In such situations, they might rely on favorable anecdotes instead of data to present the feature positively. (21m0s)
• Sales counterparts may highlight that the feature is not helping win deals, leading to discussions about the need for additional features to meet "table stakes." This can result in committing to more work for a feature that perhaps should not have been built initially. (22m22s)
• It is suggested that product leaders should sometimes pause for a period before making decisions, as many decisions that seem reversible are actually not, leading to increased workload and accumulated "debt" from unnecessary features. (23m48s)
• The discussion humorously compares the situation to a stand-up comedy routine, emphasizing the common challenges faced by product managers. (24m17s)
• Vanta's market-leading trust management platform assists in continuously monitoring compliance, reporting, and tracking risk. (24m47s)
• The platform allows users to save time by completing security questionnaires using Vanta AI. (24m57s)
• Thousands of global companies utilize Vanta to automate evidence collection, unify risk management, and streamline security reviews. (25m2s)
• A promotional offer provides $1,000 off Vanta services through a specific link. (25m9s)

Question two: Do I actually have good taste? (25m20s)

• At Spotify, one of the core values is to engage in more discussions and thinking, as it is considered inexpensive and valuable. (25m20s)
• A key question to consider is whether one actually possesses good taste, which is important for personal and professional growth. (25m43s)
• Early in a career at Google, there was a belief that strategy was unnecessary and that execution was the primary focus, a mindset that was prevalent among early career product managers. (26m25s)
• This belief was challenged after moving to Twitter post-IPO, where it became evident that the lack of a cohesive product strategy was a significant issue, despite the company's strong assets like its product, network effects, brand, and talent. (27m44s)
• The realization of the importance of strategy was further reinforced at Stripe, where having a clear strategy was crucial for the success of early-stage products. (29m10s)
• The concept of "taste" in product leadership extends beyond aesthetics and user experience design to include the beliefs and decisions that guide leadership and management. It involves evaluating what to learn, who to learn from, and what content to engage with. (29m30s)
• Developing good taste requires the ability to identify quality without relying on obvious results. This skill is exemplified by recognizing talent or potential before it becomes widely acknowledged, as illustrated by the example of Jensen Wang of Nvidia. (31m41s)
• As individuals gain seniority and success, there is a tendency to become overly critical, dismissing many things as inadequate. This behavior does not demonstrate good taste, as it is easy to criticize without offering constructive insights. (33m28s)
• There is a tendency to become overly enthusiastic about catchy metaphors, such as "one-way door" and "two-way door" decisions, which can oversimplify complex concepts. (34m4s)
• The concept of reversible and irreversible decisions is discussed, highlighting how catchy metaphors like "two-way door" and "one-way door" gained popularity due to authority bias, as exemplified by Jeff Bezos. (34m23s)
• The influence of alliteration on the attractiveness of ideas is examined, using examples like "fail fast" versus "fail quickly" and "fast follow," suggesting that the appeal often lies in the phrasing rather than the concept itself. (35m6s)
• There is a tendency to be impressed by complex charts and mathematics that are not fully understood, which some product leaders use strategically. (35m59s)
• A personal realization is shared about the importance of evaluating ideas independently of social and authority proofs, which led to significant growth as a product leader and improved critical thinking skills. (36m28s)
• A brief mention is made of note-taking preferences, with a preference for simple tools like a pen with multiple colors and a clipboard, rather than digital apps. (37m49s)

Question three: Why does my job feel so frustrating? (38m9s)

• The job of a PM leader can be extremely lonely, which contributes to daily frustrations despite a love for the role. (38m26s)
• Frustration in a job often arises from operating in misalignment with one's core strengths and superpowers. (39m12s)
• Work can be categorized into three levels: impact, execution, and optics. Frustration occurs when forced to operate outside one's preferred level. (39m53s)
• Many product leaders prefer the execution level, but as they advance, they must spend more time on optics, which can lead to dissatisfaction. (40m50s)
• The solution to job frustration is to abandon traditional career paths and societal expectations, focusing instead on aligning work with personal strengths and preferences. (41m26s)
• Identifying and working in accordance with one's superpowers leads to fulfilling and effective work, reducing frustration. (43m3s)

Question four: Am I really listening? (43m29s)

• The final question to consider is, "Am I really listening?" This question is challenging because it requires a deeper understanding of listening beyond basic actions like recapping and making eye contact. (43m38s)
• Recognizing a more profound level of listening is essential for becoming a world-class leader. (43m59s)
• For further insights on effective listening, it is recommended to explore the perspectives of Rick Rubin, Dee Hock, and Peter Drucker. (44m17s)

Closing remarks (44m35s)

• The closing remarks include an invitation to hang out in the back part of the room quietly after the session. (44m35s)
• There is a brief mention of taking a group selfie, with the lights being turned on for the picture. (44m52s)
• Listeners are thanked for their attention and encouraged to subscribe to the show on platforms like Apple Podcasts and Spotify. (45m6s)
• A request is made for listeners to rate or review the podcast to help others discover it. (45m15s)
• Information is provided on accessing past episodes and learning more about the show at LennyPodcast.com. (45m22s)