Navigating Product Management within Constraints

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 management

(01:12:35) Summarizing the 3 steps

(01:16:36) Lightning round and final thoughts

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Referenced:

• Pitchfork: https://pitchfork.com/

• Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/

• How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy

• Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri

• Mailchimp: https://mailchimp.com/

• Intuit: https://www.intuit.com/

• Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/

• The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina

• Miro: https://miro.com/

• Prioritizing: https://www.lennysnewsletter.com/p/prioritizing

• Temptation Island on Netflix: https://www.netflix.com/title/81744518

• Mark L. Walberg’s website: https://markwalbergtv.com/about

• Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/

• Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp

• Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/

• Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/

• RedMonk: https://redmonk.com/

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Recommended books:

• Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r

• Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ

• Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/

• Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028

• The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/

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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.