Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

Sep 18, 2022 Episode Page ↗
Overview

Lenny interviews Jason Shaw, a product leader from Yammer, Microsoft, Amazon, Airbnb, and Alchemy. They discuss Web3 PMing, effective leadership, the Amazon "working backwards" process, and career advancement strategies like "ladder vs. map."

At a Glance
18 Insights
1h 10m Duration
12 Topics
4 Concepts

Deep Dive Analysis

Jason Shah's Career Background and Journey to Web3

Current State of Web3 and Navigating Crypto Winter

Evolution of Product Management in Web3

Amazon's Impact on Jason's Product and Leadership Philosophy

Amazon's 'Working Backwards' Process and Communication Clarity

Key Traits of Effective Leaders

How to Influence CEOs and Founders Effectively

Career Ladder vs. Career Map Framework

When to Pursue New Opportunities vs. Stick it Out

Effective Hiring Strategies: Marketing, Sales, and Product Mindsets

Most Important Skill for Product Managers

Lightning Round: Book, Companies, TV Show, Interview Question, Vegetable

Working Backwards Process

An Amazon-originated product development approach that starts by defining an ideal end-state, usually by writing a press release (PR) and frequently asked questions (FAQ) for the product before it's built. This process forces clarity of thought and ensures every word and feature is intentional and customer-focused.

Pushback (Reframed)

Instead of viewing 'pushback' as disagreeing or saying no, it's reframed as shifting direction or helping the business succeed when there's a disagreement. This involves understanding the underlying goal or issue and aligning on a shared objective, often through a bigger, more exciting idea.

Career Ladder vs. Map

The 'career ladder' mindset focuses on moving up in title, influence, and power within a traditional career path. The 'career map' mindset prioritizes interesting experiences and personal growth, viewing a career as a journey with diverse experiences, even if it involves discomfort or non-linear moves.

Growth Operations

A newly created role or area, particularly in Web3 companies, that combines aspects of growth product and growth marketing. It focuses on driving growth through operational strategies and processes, adapting to the unique opportunities and challenges of the business.

?
How would you describe the current state of Web3?

Despite a drop in prices and financial scandals, Web3 is in its strongest position ever, with record Ethereum transactions, new Layer 2 technologies, and increasing product development and user adoption, indicating a maturation of the space.

?
How do you maintain team morale and focus during challenging times like 'crypto winter'?

The only way to maintain morale is to make progress. Focusing on shipping products, building new features, and seeing tangible development keeps teams motivated and effective, especially when hiring people who are intrinsically motivated by building.

?
How is the role of a Product Manager evolving in Web3?

The need for PMs in Web3 is increasing as products mature, complexity grows, and the market becomes more competitive. Teams are hiring product leaders at all levels, shifting towards more traditional product management functions alongside community management and marketing roles.

?
What makes a great leader?

Great leaders demonstrate humility by believing nothing is 'above them,' are deeply involved in the details of their craft, and are adaptable to new information and changing situations, rather than rigidly adhering to past playbooks.

?
How can one effectively influence a CEO or founder's direction when there's a disagreement?

Instead of 'pushing back,' focus on understanding the CEO's ultimate goal or what excites them, then reframe your proposal to align with that objective. This involves presenting a bigger, more exciting idea that achieves shared goals, rather than just saying no or focusing on constraints.

?
What is the most important skill for Product Managers to advance their careers?

The most important skill is understanding and defining what problem truly matters. This clarity guides product building, motivates teams, and affects overall business strategy, ensuring efforts are directed towards impactful solutions.

1. Define the Core Problem

Develop the crucial skill of clearly understanding and defining the core problem you are trying to solve. This clarity guides product development, motivates the team, and impacts overall strategy and business model.

2. Reframe Pushback as Alignment

Reframe “pushback” as “shifting direction” or “helping the business succeed” by understanding the other person’s goal and aligning with it. This fosters a positive mindset focused on shared objectives rather than disagreement.

3. Influence by Aligning with CEO

When trying to influence a CEO or founder, frame your proposals by working backwards from what excites them, how they perceive the world, and what they prioritize. This approach makes your pitch more resonant and effective.

4. Cultivate Ownership & Responsibility

Foster a sense of responsibility and ownership within your team by encouraging them to feel personally invested in the company, product, and environment. This drives intrinsic motivation beyond top-down accountability measures.

5. Master Your Craft’s Details

Leaders should audit the details of their work, deeply understanding things at a low level to reason effectively and make informed decisions. This attention to detail ensures high quality and efficacy in one’s job.

6. Embrace Humility as a Leader

As a leader, believe that nothing is “not my job,” demonstrating humility and willingness to engage with any task. This sets a powerful example and earns respect from your team.

7. Adapt to New Information

Be a flexible leader who adapts to new information and situations, rather than rigidly adhering to past playbooks or philosophies. This allows for effective navigation through change and unique opportunities.

8. Use Amazon’s Working Backwards

Utilize the “working backwards” process by writing a PRFAQ (Press Release and Frequently Asked Questions) for a new product or proposal. This mechanism forces clarity by defining an ideal end state and articulating the product’s value and impact as if it were already launched.

9. Write with Concision & Clarity

Improve communication by using concrete numbers over subjective adjectives, practicing strict concision, and ruthlessly editing to remove unnecessary words. This forces clarity of thought and makes every word more impactful.

10. Structure PRFAQ Documents

When creating a PRFAQ, structure it with an introduction announcing the product, followed by sections for the problem, solution, a customer quote, a leadership quote, and a clear call to action. This ensures comprehensive and customer-centric communication.

11. Simulate Customer Experience

Practice customer obsession by including a detailed customer quote in your PRFAQ that vividly describes their experience with the product. This forces you to think from their perspective and articulate specific benefits.

12. Drive Morale Through Progress

Maintain team morale during challenging times by focusing on making tangible progress and shipping products. People get excited and motivated by seeing real advancements, more so than by speeches or extrinsic motivators.

13. Choose Map Over Ladder

Approach career advancement using a “map” framework, prioritizing interesting experiences and personal growth over a linear “ladder” climb for title or power. Be intentional about the macro picture of your career, not just micro-level job details.

14. Iterate on Role as Product

Approach job descriptions and roles with a product mindset, iterating on them flexibly based on candidate interactions and evolving business needs. This ensures the role is crafted to make the person successful rather than just checking a box.

15. Sell to Candidate’s Motivations

During the hiring process, act like a salesperson by actively listening to candidates’ pain points and understanding their core motivations. Effectively communicate how the role aligns with their goals to ensure a good fit and long-term happiness.

16. Market Your Company’s Brand

Develop a positive brand and reputation for your company and yourself as an individual to attract candidates. This ensures potential hires know about your company and its culture before they even step in the door to interview.

17. Embrace Traditional PM in Web3

As Web3 products mature and the market becomes more competitive, embrace traditional product management roles and practices. Recognize that product management is a competitive advantage for strategy, execution, and team collaboration.

18. Cultivate CEO Mindset

Read “The Hard Thing About Hard Things” to cultivate a CEO-like mindset of extreme dedication and focus on outcomes, even through difficult challenges. This perspective is valuable for product managers to care deeply about results.

I couldn't imagine a word more viscerally that makes you feel like you're sort of physically going against what somebody else wants. And it gears people into a mindset of then, well, how should I push back? It starts from a place of, I need to disagree. I need to say no. It's a very negative mindset purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something?

Jason Shah

I think people get really excited when they see progress.

Jason Shah

I think the two together, humility and being excellent at craft, I think is a very potent combination, especially when you throw in the last thing of being able to adapt to any situation.

Jason Shah

I care more about living in a really interesting life than let's say a good or comfortable life.

Jason Shah

Fewer words means every word is, you know, 10 pounds in weight instead of one. And that means that the decisions you're making, the trade-offs are far more intentional.

Jason Shah

Amazon's PRFAQ (Press Release and Frequently Asked Questions) Document Structure

Jason Shah
  1. Write an introduction announcing the product.
  2. Describe the problem the product solves in one clear paragraph.
  3. Briefly describe the product solution.
  4. Include a customer quote, putting yourself in the shoes of a specific user and detailing their experience.
  5. Include a leadership quote, explaining how the product fits into the company's strategy.
  6. Provide a clear call to action, detailing availability and access for customers.
100 people vs. 5,000+ people
Uniswap vs. Coinbase team size comparison Uniswap has done more daily volume on certain days than Coinbase despite a significantly smaller team.
85-90%
Revenue drawdown at Airbnb during COVID Referring to the significant drop in Airbnb's revenue during the early days of the COVID-19 pandemic.
30-40%
Percentage of founder's time on recruiting A benchmark for the amount of time founders should spend on recruiting, highlighting its importance.