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

Sep 18, 2022 1h 10m 18 insights Episode Page ↗
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."
Actionable Insights

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.