Failure

Dec 13, 2023 1h 1m 25 insights Episode Page ↗
This compilation episode explores valuable lessons from product and leadership failures, featuring insights from Katie Dill (Stripe), Paul Adams (Intercom), Tom Conrad (Zero Longevity Science), Sri Bachu (Ramp), Jay-Z (Webflow), and Maggie Crowley (Toast). It emphasizes learning from setbacks, building trust, and strategic product development.
Actionable Insights

1. Prioritize Problem Over Solution

As a product manager, resist the urge to jump to solutions or get attached to a specific build; instead, focus first on deeply understanding user problems and identifying opportunities.

2. Build Products from User Needs

Avoid building products primarily out of competitive fear; instead, focus on deeply understanding user struggles and aiming to create something wonderful for them.

3. Build Trust Through Listening

When joining a new team or leading change, prioritize listening to understand individuals’ motivations and concerns before implementing changes, as this builds trust and ensures buy-in.

4. Validate Unit Economics Early

Ensure that unit economics work right from the beginning, rather than relying on ‘magical thinking’ that they will scale to profitability later.

5. Understand Business as Math Problem

Beyond great product execution, recognize that a company is fundamentally a ‘math problem’ where investment must lead to returns, and a broken foundational equation cannot be fixed by execution alone.

6. Leverage Strategic Strengths

Build solutions that align with your company’s strategic strengths (e.g., a platform leveraging reviews) rather than trying to build new operational muscles from scratch where you lack expertise.

7. Define Failure as ‘Not Learning’

Cultivate a culture where failure is defined as ’not learning’ rather than simply not driving revenue, and celebrate failures that yield conclusive insights.

8. Design Conclusive Failure Experiments

To ensure learning, design experiments that can fail conclusively, especially in B2B where a large ‘N’ is rare, by maximizing the treatment effect with all possible tactics.

9. Embrace ‘Ship to Learn’ Culture

Adopt a culture of ‘ship fast, ship early, ship often’ to embrace failure as a learning opportunity, allowing for rapid iteration and improvement.

10. Dogfood Your Product & Experiments

Regularly use and test your own product and experiments (dogfooding) to quickly identify flaws or uncompelling features, especially before broader rollout.

11. Cultivate Resilience in Your Career

Develop resilience and self-belief to navigate the inevitable setbacks, rejections, and ‘B-moments’ throughout your career, consistently getting back on track after failures.

12. Embrace the Long Arc of Career

Recognize that a career is a long journey with many opportunities for change and growth; don’t stress if progress isn’t as fast as desired, as things can take off later.

13. View Failures as Growth Opportunities

Recognize that experiences of failure can make you better and open new professional doors, even high-profile ones, providing invaluable learning.

14. Acknowledge Your ‘B-Sides’

Recognize that everyone has ‘B-moments’ (setbacks, failures, periods of struggle) in their career alongside ‘A-sides’ (achievements), and understanding this helps maintain resilience and perspective.

15. Reflect on Product Failures

Regularly reflect on and be able to articulate your worst product shipments, as acknowledging and understanding these failures is a sign of experience and a critical part of a product manager’s growth.

16. Avoid Product Rewrites

Generally avoid full product rewrites, especially if they skip crucial steps like discovery, one-pagers, and thorough technical/design research, as they often lead to prolonged timelines and feature parity issues.

17. Beware Excess Investment

Be cautious of having an excess of investment, as it can lead to irrational spending and an unwinnable arms race, making unwise decisions more likely.

18. Target Problems with Tailored Solutions

Instead of using one blunt instrument (e.g., universal inspection) to solve broad problems, identify specific user problems and apply tailored, cost-effective solutions (e.g., lockboxes for security, cleaning partnerships for cleanliness).

19. Conduct Formative User Research

When doing tactical research, also dedicate time (e.g., 20 minutes per session) to formative research to map out users’ social networks and communication patterns, uncovering deeper needs.

20. Inflict Change With People

To make truly positive and impactful change, bring people along with you rather than inflicting change upon them, as trust is the key element for collaborative improvement.

21. Navigate Quality vs. Speed Tension

Acknowledge and navigate the inherent tension between maintaining high quality standards and the need to ship fast and learn, encouraging both craft and iterative development.

22. Embrace Public Speaking Setbacks

If you freeze or make a mistake during public speaking, adapt and continue, as these things are not as big a deal as they seem and you can recover.

23. Master Your Career Narrative

Understand that career success isn’t just about accomplishments, but also about effectively telling your story and framing your experiences in a way that highlights their value to others.

24. Reignite Passion Through New Challenges

If you feel burnt out or disconnected from your industry, consider taking on new, even short-term or unconventional, challenges to reignite your passion and remind yourself of the rewards of building.

25. Validate Localized Assumptions On-Site

When expanding internationally, validate critical user assumptions (e.g., UI language preferences, learning goals) with on-site research, as local nuances can drastically impact product adoption.