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

Oct 31, 2024 Episode Page ↗
Overview

Shreyas Goshi shares three questions, plus a bonus, he wished he'd asked himself sooner as a PM leader. He discusses overcoming busyness, developing good taste, managing career frustration, and the true meaning of listening.

At a Glance
5 Insights
45m 34s Duration
8 Topics
5 Concepts

Deep Dive Analysis

Shreyas's Career Reflections and Unasked Questions

Question 1: Why Product Leaders Are Always Busy

Annual Planning as an Example of Busyness

The Illusion of Two-Way Doors in Decision-Making

Question 2: Developing Good Taste in Product Leadership

The Dangers of Catchy Metaphors and Authority Bias

Question 3: Understanding Job Frustration and Superpowers

Question 4: The True Meaning of Effective Listening

Scope as an Immovable Force

As product careers advance, the scope of responsibility grows so large that no amount of efficiency or prioritization techniques can prevent a product leader from feeling incredibly busy. This overwhelming scope is a fundamental challenge that productivity hacks alone cannot solve long-term.

Two-way vs. One-way Doors for PMs

While the concept of 'two-way doors' (reversible decisions) suggests quick action, for most PM leaders, decisions that appear reversible often become 'one-way doors' due to practical realities. Committing to features without deep thought can lead to accumulating technical and product debt, making PMs busier.

Product Taste (Beyond UI/UX)

Taste is the ability to identify what is truly good without needing to see its results. For product leaders, this extends to discerning valuable beliefs, learning sources, and ideas, rather than being swayed by superficial factors like catchy metaphors, alliterations, or authority bias.

Three Levels of Product Work

Product work can be categorized into three levels: Impact, Execution, and Optics. Experiencing frustration in a product leadership role often stems from spending most of one's time operating at a level that is misaligned with one's natural strengths or 'happy place'.

Real Listening

Beyond superficial actions like hearing, recapping, and making eye contact, real listening involves an entirely deeper, less commonly understood level of engagement. This profound form of listening is identified as a critical skill for world-class leadership.

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Why do product leaders often feel overwhelmed and busy despite using productivity techniques?

Product leaders often feel overwhelmed because as their careers advance, their scope grows so large that no amount of efficiency or prioritization techniques can fully manage it. The core issue is often the sheer volume of work and commitments, rather than a lack of personal productivity.

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How can product leaders reduce busyness and avoid accumulating unnecessary work?

One way is to develop a clear, aligned product strategy, which can significantly streamline planning and prioritization, reducing the need for lengthy annual planning cycles. Another is to pause and rigorously think through product decisions, as many 'two-way door' decisions for PMs are actually one-way doors that lead to accumulating debt.

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What does 'good taste' mean for a product leader, beyond just design or user experience?

Good taste for a product leader involves the ability to identify what is truly good and valuable without needing to see its immediate results or being swayed by superficial factors like catchy metaphors, alliterations, or authority figures. It's about discerning sound principles and ideas independently.

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Why do product leadership roles often feel frustrating, even if the overall job is loved?

Job frustration often arises when product leaders spend most of their time operating in misalignment with their 'superpowers' or preferred level of work (Impact, Execution, or Optics). Forcing oneself to operate consistently outside one's natural inclination, especially at the 'optics' level as one ascends, can lead to unhappiness and frustration.

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How can a product leader truly listen effectively?

True effective listening goes beyond superficial actions like hearing, recapping, and making eye contact. It involves an entirely deeper level of engagement that is less commonly understood but is essential for world-class leadership, with Rick Rubin, Dee Hock, and Peter Drucker cited as resources for further understanding.

1. Align Work with Superpowers

Identify your core strengths and preferred operating level (impact, execution, or optics) and make career decisions that align with them, rather than following traditional paths or external expectations, to avoid frustration and maximize impact.

2. Practice Deeper Listening

Go beyond superficial listening (recapping, eye contact) to discover a deeper level of understanding, which is essential for becoming a world-class leader. Explore resources from Rick Rubin, D-Hawk, and Drucker for guidance.

3. Develop Clear Product Strategy

Spend upfront time creating a real product strategy that everyone is aligned with to significantly reduce time spent on annual planning and make prioritization easier.

4. Pause Before Product Decisions

Take time (two minutes to two weeks) to thoroughly think through product decisions, considering customer motivation, differentiation, and distribution, as most ’two-way doors’ are actually one-way and lead to accumulating unnecessary work.

5. Cultivate Critical Thinking

Develop ‘good taste’ by evaluating ideas based on their merit, independent of catchy metaphors, alliterations, social proof, or authority bias, to become a more critical thinker.

Most doors that look like two-way doors are actually one-way doors. They are two-way doors at Bezos' level. But as a PM leader, for you, they are a one-way door. And that's what's making you busy.

Shreyas Doshi

Taste is about the ability to identify what is really good without needing to see its results.

Shreyas Doshi

It requires zero taste right now for anybody to say, oh, that CEO of NVIDIA is a genius, right? Jensen is a genius. If you are saying that in 2024, it actually requires zero taste, because you can just look up NVIDIA stock price.

Shreyas Doshi

Thinking is cheap, so you should do more thinking, not less.

Shreyas Doshi

Plans are useless, but planning is everything.

Shreyas Doshi

To thine own self be true.

Shreyas Doshi

Developing Better Product Taste

Shreyas Doshi
  1. Recognize that taste extends beyond UI/UX to evaluating beliefs and learning sources.
  2. Identify what is truly good without needing to see immediate results or social proof.
  3. Be wary of being overly excited by cool metaphors (e.g., 'two-way door'), alliterations (e.g., 'fail fast'), or complicated charts/math you don't understand.
  4. Evaluate ideas separately from social proof and authority proof.
  5. Cultivate critical thinking by shedding ingrained patterns and biases.

Reducing Job Frustration by Aligning with Superpowers

Shreyas Doshi
  1. Identify your preferred level of product work (Impact, Execution, or Optics) where you operate best.
  2. Recognize that higher corporate levels often require more time at the 'optics' level, which may not be your default or happy place.
  3. Be honest with yourself about whether your current role aligns with your superpowers and preferred operating level.
  4. Consider abandoning traditional career paths if they force you into misalignment, rather than pushing through against who you truly are.
  5. Make career decisions based on your true self and superpowers, not external expectations, envy, or social validation.
16 or 17 years
Duration Shreyas was incredibly busy in his product career Out of 20 years in product work, before finding solutions to manage scope.
4 to 6 weeks
Typical duration for annual planning for high-level managers Involves spreadsheets, meetings, dependencies, priorities, and stakeholder engagement.
3 days
Time Shreyas spent on annual planning with a clear strategy For a major product (Stripe Connect) after developing a real, aligned product strategy.
5-6 weeks
Typical time to build a product feature Plus a couple more weeks to ramp it up.
Around 50 people
Team size where 'optics' work becomes significant for a leader Shreyas noted this as a point where he realized he would have to spend a lot of time on optics, leading to frustration.