Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)

Aug 18, 2024 1h 28m 19 insights Episode Page ↗
Kevin Yen, Product Lead at Stripe, shares unique insights on becoming a successful PM, including starting in engineering/design/sales, the importance of writing, keeping a decision log, and automating user research. He also discusses hiring with 'unsell emails' and lessons from failure.
Actionable Insights

1. Separate Identity from Job Outcomes

When facing setbacks like layoffs, distinguish between the business not needing your skills or a poor fit, and your actual competence. This helps re-evaluate what’s in your control and find a better environment.

2. Start Elsewhere Before PM

If aspiring to be a great Product Manager, start in roles like engineering, design, or sales. This provides foundational exposure to building, understanding customer problems, and brings a unique, insightful perspective to product development.

3. Cultivate Great Writing Skills

Product Managers must be great writers because writing creates clarity at scale, both internally and externally. The ability to write compelling messages in the customer’s voice is crucial, as you can’t build a product effectively if you can’t sell or support it.

4. Maintain a Decision Log

Keep a log of decisions you make, their rationale, and their outcomes. Practice by analyzing decisions made by other teams or companies, predicting outcomes, and reviewing them later to improve your ‘product sense’ (making good decisions with insufficient data).

5. Automate B2B User Research

PMs need direct exposure to raw customer material. Use platforms like userinterviews.com to source specific customer profiles, and integrate tools like Gong (for sales call alerts) with Zapier and Customer.io to automatically schedule interviews with relevant customers.

6. Draw the Problem Perimeter

As a PM, define clear constraints for your team, such as target customer segments, jobs-to-be-done, availability (e.g., web/mobile), and core product principles (e.g., speed over data consistency). This allows engineers and designers to innovate creatively within well-defined boundaries.

7. Implement an “Unsell Email” for Hiring

At the offer stage, send an email (3-8 bullet points) detailing potential downsides or fears candidates might have about the role or company (e.g., work-life balance at a startup). This helps identify truly committed A+ hires and prevents early departures due to misaligned expectations.

8. Talk to Customers Constantly

Never stop engaging directly with customers, even if you feel you ‘know’ them. The world and customer needs are constantly evolving, and continuous exposure to these micro-changes is essential for building relevant and successful products.

9. Always Seek the “Additional 3%”

Don’t just meet the minimum requirements of your job or product. Continuously challenge yourself to find and do the ‘additional 3%’ beyond what’s expected, fostering personal growth and creating more delightful products.

10. Conduct Silent Document Reads

To gather effective feedback, schedule dedicated meeting time (e.g., 20 minutes) where team members silently read and comment on documents in real-time. This focused approach speeds up the feedback cycle and ensures deeper engagement than asynchronous reviews.

11. Obsess Over Final Deliverable Details

As a PM, don’t delegate all granular details of the user experience. Be deeply involved in fine-tuning aspects like animation timing, as these small details can significantly impact product adoption and overall quality.

12. Read Compelling Writing to Improve

To become a better writer, consume as much good, compelling writing as possible from diverse sources (e.g., Paul Graham essays, sci-fi/fantasy). Focus on writing that pushes you to action, and practice varying sentence cadence (short, long) to maintain reader engagement.

13. Calibrate and Prioritize Deep Work

Regularly review and ‘spring clean’ your tasks to ensure you’re focusing on activities that truly deliver value to customers, rather than getting bogged down in internal processes. Be willing to push back on artificial deadlines to create space for high-quality work.

14. Invest Deeply in Candidates

As a hiring manager, be highly responsive and accommodating to candidates’ concerns during the offer stage, even if it means unconventional meeting times. This personal investment demonstrates commitment and helps secure strong hires.

15. Embrace “Everything Happens for a Reason”

Adopt the mindset that events, good or bad, are opportunities to learn and move forward. Instead of dwelling on the past, focus on your next actions, trusting that you’ll be able to connect the dots and understand the purpose retrospectively.

16. Recognize AI as a New “Crayon”

Understand that for future generations, AI tools like image generators are fundamentally new creative instruments, akin to a crayon. This perspective highlights the profound and unpredictable shifts in product expectations and user interaction that are yet to come.

17. Decision Log is Complementary, Not a Replacement

While a decision log is valuable for improving product sense, it is not a substitute for hands-on experience in building products. Continuous engagement in product development is crucial for genuine growth.

18. Build Your Own Website

Consider creating and maintaining your own website using raw HTML and CSS. This personal corner of the internet offers joy in hands-on creation and fosters a sense of ownership, even if it’s not frequently updated or shared.

19. Practice Everyday Kindness

Make a conscious effort to be kinder in daily interactions, such as saying thank you more often, holding doors, or waving in traffic. This simple practice contributes to a more positive and less conflict-driven world.