The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo)

Episode Overview

• Shreyas Doshi shares his practical and often contrarian wisdom on product management, drawn from his experiences at companies like Stripe, Google, and Twitter.
• The conversation provides a deep dive into the "premortem" exercise, a proactive framework for identifying and mitigating project risks before they lead to failure.
• Doshi breaks down the different levels of product work—execution, optics, and impact—explaining how misalignment between these levels causes common friction between PMs and leadership.
• A core argument is that most apparent execution problems, such as team misalignment or missed deadlines, are often symptoms of deeper, unaddressed issues in strategy or company culture.

Key Concepts

• Levels of Product Work: A framework explaining the different altitudes of thinking: the Execution level (how to build), the Impact level (the effect on customers and the brand), and the Optics level (the communication that bridges the two).
• The Root Cause of Execution Problems: The thesis that most issues perceived as execution failures are actually symptoms of deeper problems, such as a lack of strategic clarity or a misaligned company culture.
• Premortem Framework: A proactive exercise where teams imagine a project has already failed and work backward to identify all potential causes, fostering psychological safety and constructive criticism.
• Risk Categorization (Tigers, Paper Tigers, Elephants): A shared vocabulary for classifying risks during a premortem. "Tigers" are significant, known threats; "Paper Tigers" are perceived threats that are less dangerous than they appear; and "Elephants" are the unspoken issues everyone knows about but avoids discussing.
• Post-Premortem Action Plan: The critical final step of a premortem, where the team creates a concrete plan with owners to mitigate the most important risks identified.
• Culture by Example: The principle that effective company culture is established by leaders who consistently model the behaviors they want to see, rather than just articulating values.
• Separating Build Effort from Marketing Effort: The lesson that the marketing importance and customer value of a feature are independent of the engineering effort it took to build.

Quotes

• At 0:00 - "You should be spending some time on internal optics because it creates energy, it can create awareness, it creates excitement, it creates opportunities for feedback." - Shreyas Doshi explains why managing internal communication and perception is a valuable use of a product manager's time.
• At 0:18 - "There's no one out there today who shares more wisdom, more consistently on the art of product management than Shreyas Doshi." - The host, Lenny, introduces his guest and praises his significant contributions to the product management community.
• At 0:37 - "What I love about Shreyas is that his insights are often framed in really memorable and interesting ways, and they're often contrarian and not ideas that you've heard elsewhere." - Lenny describes the unique and memorable nature of Shreyas Doshi's advice.
• At 25:32 - "Basically separate the effort involved in building something with the effort you want to put behind talking about said thing." - Doshi explains a key marketing lesson from John Collison: the importance of a feature to customers is not always proportional to the effort it took to build.
• At 26:05 - "I learned the importance of setting the culture you want simply by consistently being an example of the behaviors you want to replicate in the organization." - Doshi describes how the Stripe founders established company culture by modeling it themselves rather than just talking about it.
• At 28:22 - "Why do we need to wait until after things go wrong? Because why can't we extract some of these insights before they go wrong?" - Doshi explains the proactive motivation behind conducting premortems instead of just postmortems.
• At 29:31 - "Imagine this project that we are working on has failed six months from now...Now, let's work backwards from there and ask ourselves, what went wrong? What could have contributed to this utter failure?" - Doshi shares the core prompt that frames a premortem meeting.
• At 30:38 - "And then the last one is elephant, and the elephant is the elephant in the room that nobody is talking about." - Doshi defines an "Elephant" as a known but unspoken issue within the team.
• At 31:35 - "I like to create a post-premortem action plan, and then share that with the team and kind of keep myself as the leader accountable for actually making progress on it." - Doshi explains the crucial final step of a premortem is to create an actionable plan to mitigate the identified risks.
• At 56:05 - "The reason is that you are thinking at different levels." - Shreyas Doshi explains the fundamental reason for disconnects between product managers and CEOs, with PMs often focusing on execution and CEOs on impact.
• At 56:22 - "You are fixated on the execution level, which is what does it take to get something done and how can I do it? How can I hit the next milestone?" - Doshi describes the typical mindset of a product manager who is deep in the details of a project.
• At 58:35 - "Optics is about creating awareness of the impact and the execution that you are doing." - Doshi provides a concise definition for the "optics level" of product work, framing it as the essential communication layer that connects execution to impact.
• At 59:33 - "The challenge with optics is that in certain organizations, that balance gets thrown off where optics sometimes becomes the goal." - He warns that while optics are important, they can become counterproductive if a company's culture starts rewarding the appearance of progress over actual results.
• At 1:04:00 - "Most execution problems are actually strategy problems or culture problems." - This is a central, provocative idea suggesting that when teams struggle with execution, leaders should look for root causes in the company's strategy or culture.
• At 1:07:30 - "It's just a band-aid... the execution problem is going to manifest in different ways a month down the road." - He explains that trying to solve strategy or culture problems with more process (e.g., more meetings) is an ineffective, short-term fix.

Takeaways

• When facing recurring execution issues, resist the urge to add more process and instead investigate for underlying strategic ambiguity or cultural misincentives.
• Implement premortems before starting major projects by framing the conversation around hypothetical failure to create psychological safety and encourage honest risk assessment.
• Ensure every premortem concludes with a concrete "post-premortem action plan" with clear owners to mitigate the most critical risks.
• When communicating with leadership, consciously shift from the "execution level" (the 'how') to the "impact level" (the 'why' and its effect on customers) to bridge communication gaps.
• To build a strong culture, focus on consistently demonstrating the behaviors you want to see, as modeled actions are far more powerful than stated company values.
• Decouple your marketing and launch plans from the engineering effort a feature required; base promotional energy on what delivers the most customer value.
• Use a shared vocabulary like "Tigers, Paper Tigers, and Elephants" to help your team categorize and discuss project risks more effectively.
• Strategically manage "internal optics" not as self-promotion, but as a tool to build energy, create awareness, and gather valuable feedback for your team's work.
• Recognize that adding more meetings is often an ineffective "band-aid" for deeper strategy or culture problems and is unlikely to provide a long-term solution.