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The one question that saves product careers | Matt LeMay

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Aug 14, 2025

Guest

Matt LeMay

Matt LeMay, a prominent product leader and author, draws from his extensive experience to discuss the crucial question that can predict team survival in layoffs. He reveals how adhering strictly to so-called best practices can lead to irrelevance. Listeners will discover strategies to align product efforts with business objectives, navigate challenges without saying 'no,' and the importance of curiosity in team dynamics. He also shares a personal anecdote about a controversial music review that shaped his views on accountability and creativity in product management.

01:32:09

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Episode notes

00:00 / 00:00

Ask If You’d Fund Your Own Team

Ask your team: “If you were the CEO, would you fully fund this team?”
Use the answer to identify gaps and decide what changes are needed to be a clear business investment.

00:00 / 00:00

How The Low-Impact Death Spiral Starts

The low-impact PM death spiral starts with easy, visible features that feel safe but add complexity.
Accumulated low-impact work makes high-impact projects harder, forcing more low-impact work and dependency layers.

00:00 / 00:00

MailChimp First-Email Turnaround

At MailChimp a PM rallied teams to improve first-email success instead of adding new features.
They simplified the experience and hit an ambitious business metric by collaborating across domains.

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The Interconnection of Music and Product Development

05:06 • 2min

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Aligning Product Teams with Business Outcomes

06:45 • 21min

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Navigating Product Management Challenges

27:47 • 12min

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Navigating Product Management within Constraints

40:05 • 4min

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Aligning Goals for Impact

44:23 • 29min

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Cultivating Curiosity for Team Success

01:13:00 • 8min

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Entertainment, Growth, and Reflection

01:20:32 • 12min

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#1673

• Mentioned in 15 episodes

Escaping the Build Trap

How Effective Product Management Creates Real Value

Melissa Perri

In 'Escaping the Build Trap', Melissa Perri addresses the common issue where organizations become trapped in a cycle of constantly building features without focusing on the value these features bring to customers. She argues that success should be measured by outcomes rather than outputs. The book provides practical frameworks, real-world examples, and strategies for transitioning from a 'feature factory' mindset to one that emphasizes continuous discovery, customer needs, and strategic product management. Perri emphasizes the importance of defining a clear product vision, empowering product teams with autonomy, and aligning organizational dynamics to deliver real value. The book is essential for product managers, leaders, and anyone involved in product development who want to create meaningful products and drive business impact.

#34389

Product Management in Practice

Matt LeMay

This book provides actionable insights into the day-to-day challenges of product management, emphasizing the CORE connective skills (Communication, Organization, Research, Execution) required to align user needs with business goals. It covers real-world tactics for collaboration, user research, goal-setting, and Agile implementation, while addressing common behavioral pitfalls in product management.

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• Mentioned in 15 episodes

The wisdom of insecurity

A Message for an Age of Anxiety

Alan Watts

In this book, Alan Watts draws on Eastern philosophy and religion to argue that true security and peace can only be achieved by understanding and embracing the impermanence and insecurity of life. He critiques the modern quest for security and certainty, highlighting the futility of chasing moving goalposts such as financial success, stability, or escape from pain. Watts emphasizes the importance of living in the present moment, letting go of the past and future, and accepting the uncertainty of life to find true freedom and fulfillment.

#10916

• Mentioned in 3 episodes

Impact First Product Teams

Matt LeMay

Matt LeMay's "Impact First Product Teams" is a guide for product teams seeking to directly contribute to business success. The book emphasizes the importance of understanding and aligning with overall business objectives, moving beyond simply completing tasks. LeMay encourages product managers to think critically about the value their work brings to the company and to communicate this effectively. The book uses powerful questions to challenge assumptions and prompt teams to prioritize high-impact initiatives. It's a practical resource for product teams aiming to maximize their contribution to the bottom line.

#3933

• Mentioned in 7 episodes

Radical Focus

Achieving Your Most Important Goals with Objectives and Key Results

Christina Wodtke

Radical Focus tackles the OKR movement and better goal setting through the story of Hanna and Jack's struggling tea startup. When they receive an ultimatum from their only investor, they must learn to employ OKRs with radical focus to achieve their goals. The book, written in the form of a fable, pulls from Wodtke's experience with Silicon Valley companies to teach how to inspire a diverse team, stay motivated despite setbacks, and create a framework for regular check-ins and key results. The second edition includes new material to help OKR users in larger companies create, grade, and manage OKRs effectively.

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.

To hear more, visit www.lennysnewsletter.com

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