Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss: • Why aspiring PMs should start in engineering, design, or sales • The importance of writing skills, and how to become a better writer • How to automate user research • Kevin’s “unsell email” technique for hiring • The value of keeping a decision log • Insights on AI and its impact on future generations • Lessons from failure — Brought to you by: • BuildBetter—AI for product teams: https://buildbetter.ai/lenny • OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ Find the show notes and transcript at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien Where to find Kevin Yien: • X: https://x.com/kevinyien • LinkedIn: https://www.linkedin.com/in/kevinyien/ • Website: https://kevinyien.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Kevin’s background  (02:00) The story behind Kevin’s profile picture (08:41) The role of a product manager (10:48) Getting started in product management (12:47) The importance of writing skills (15:06) Becoming a better writer (19:10) The PM’s role with engineering and design (28:41) Drawing the perimeter for your team (31:37) Feedback tips (35:13) Decision logs and product sense (45:36) Unorthodox hiring strategies (47:01) The unsell email strategy (54:01) Automating user research (01:02:27) AI in everyday life (01:06:05) Lessons from failure (01:14:34) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.