Podcast Episode Details

The one question that saves product careers | Matt LeMay

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Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things.

In this conversation, you’ll learn:

1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it)

2. Why following product “best practices” perfectly can actually accelerate your path to unemployment

3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant

4. How to push back on executives without saying “no” (the options, plus a recommendation framework)

5. The counterintuitive reason why the happiest PMs are also the most commercially minded

6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management

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Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny

Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/

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Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation

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Where to find Matt LeMay:

• Instagram: https://www.instagram.com/mttlmy

• LinkedIn: https://www.linkedin.com/in/mattlemay/

• Website: https://mattlemay.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Matt LeMay

(04:23) Matt’s background and transition to product management

(06:47) The goal of Matt's new book

(12:00) How to stress test your thinking as a PM

(15:32) Thinking like the CEO

(17:33) The role of a product manager

(23:36) The low-impact PM death spiral

(27:47) Case study: Mailchimp’s transition to a platform company

(32:53) Radical acceptance

(41:24) Embracing constraints in product management

(44:23) Steps to become an impact-first product team

(49:38) Setting effective goals

(01:02:15) Prioritization and impact estimation

(01:07:58) Navigating stakeholder ma

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Published on 3 weeks, 5 days ago