Lenny's Podcast: Product | Career | Growth

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

October 31, 2024

AI Summary

5 min read

Shreyas Doshi, a product leader who worked at Google, Twitter, and Stripe, shares four questions he wishes he'd asked himself much earlier in his career. These questions form a mental framework for sharper decision-making in product management, helping leaders focus on high-impact work amid endless options and pressures.

Question 1: Is this a must-win battle?

Doshi explains that not every opportunity or feature is worth pursuing. He advises evaluating whether a problem or project is truly a "must-win"—one where losing means significant competitive disadvantage or business harm. He contrasts this with "nice-to-haves," using examples from his time at Twitter where prioritizing must-wins like core user retention over peripheral features led to better outcomes. The tradeoff is saying no to 90% of ideas to protect time for the vital 10%.

Question 2: What does great look like?

Before diving into execution, Doshi stresses defining a clear, measurable vision of success. This avoids vague goals and mid-project pivots. He shares how at Stripe, explicitly outlining what "great" payment flows looked like upfront aligned teams and accelerated progress. Alternatives like iterative guessing waste resources; the mechanism is backward-planning from the end state to current gaps.

Continue reading the full summary in the app — free to try.

Read Full Summary →

Free • No credit card required

Open in App

What you'll learn

1 `* (00:00) **Episode Intro and Guest Background**`
2 `* (03:45) **Question 1: What’s the one thing I’m optimizing for?**`
3 `* (14:20) **Question 2: Am I playing a finite or infinite game?**`
4 `* (27:10) **Question 3: What would success look like in 3 years?**`
5 `* (39:50) **Question 4: How much of this is signal vs. noise?**`
6 `* (52:30) **Applying the Questions to Careers and Products**`
7 `* (1:07:15) **Wrap-Up and Key Takeaways**`

+ Full timestamped outline available in the app

Show Notes

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: