The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)

There's a book called Homegoing, which is about the West Coast of Africa and the impact of the slave trade.

It's not my fault, but it is my problem.

History of Burning is a book that tells a story of Indian indentured servants that were brought to Uganda to build the British railroad there.

Episode summary

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process. We discuss: 1. Why great ideas often don’t get buy-in 2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much 3. Why executives are usually optimizing for a global maximum while you are often optimizing locally 4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?” 5. Why you should go in to learn, not to convince 6. Why showing only one option is a mistake 7. Why AI will make influence more important, not less — Brought to you by: Omni —AI analytics your customers can trust Lovable —Build apps by simply chatting with AI Vanta —Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jessica Fain: • LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 — 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) Introduction to Jessica Fain (03:53) Why influence is the highest-leverage skill in product (04:47) Why great ideas fail without executive buy-in (06:00) How executives actually think (09:05) The fundamentals: context-setting, communication, and empathy (10:22) Stop pitching for approval—start co-creating with execs (12:59) Influence vs. politics (and why people get it wrong) (15:44) How to disagree with execs without losing trust (17:20) Going in to learn, not to convince (19:08) How to present ideas (26:05) The Minto-style approach and tailoring your communication to each exec (28:22) Why Jessica doesn’t like the question “What’s top of mind for you?” (30:24) Understanding incentives to unlock buy-in (32:10) Aligning product work with company strategy (35:10) Quick summary (37:31) Disarming the executive (40:49) Speed matters: why fast follow-up builds momentum (43:32) How to run high-impact meetings (the 60-second rule) (47:00) Why influencing execs is part of your job (49:15) Asking for more resources and thinking in 10x bets (52:23) What to do when your idea gets rejected (54:18) Clarifying information (56:50) How to build trust and make ideas stick (58:30) Shrinking big ideas into experiments (01:02:27) Common mistakes people make when influencing leaders (01:06:00) How to grow into your next role (01:09:32) How AI is changing influence and product work (01:17:55) Using AI to simulate exec feedback and improve pitches (01:21:15) Protecting our brains from overwhelm (01:22:44) Lightning round and final thoughts — Referenced: • Box: https://www.box.com • Slack: https://slack.com • Brightwheel: https://mybrightwheel.com • Webflow: https://webflow.com • April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood • Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua • Atlassian: https://www.atlassian.com • Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid • Calendly: https://calendly.com • Glassdoor: https://www.glassdoor.co.in/index.htm • The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai • Ethan Eismann on X: https://x.com/eeismann • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield • Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank • Checkr: https://checkr.com • Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl • Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan • How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief • Barbara Minto’s website: https://www.barbaraminto.com • How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2 • Casa: https://getcasa.com • Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix • Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles) — Recommended books: • Pachinko : https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Homegoing : https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061 • A History of Burning : https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243 • The Overstory : https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X — Production and marketing by https://penname.co/ . For inquiries about sponsoring the podcast, email [email protected] . — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

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The host mentioned 'Homegoing' as part of a discussion on historical fiction that provides insight into unfamiliar wo…

The host mentions 'Switch' to emphasize the importance of understanding how executives think and make decisions. This…

The host mentioned 'History of Burning' as part of a discussion on multi-generational historical fiction, highlightin…

Pachinko

The host mentions 'Pachinko' to illustrate the historical context of daily life and the mental load faced by individu…

Overstory

The host mentioned 'Overstory' as an example of multi-generational historical fiction that provides insight into diff…

multi-generational historical fiction(3)executive decision making(1)mental load and AI(1)

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The conversation centers on multi-generational historical fiction.
A second recurring theme is executive decision making.
Referenced books include Homegoing and Switch.
The strongest audience signal points to Readers interested in historical fiction and diverse narratives. and Product leaders and managers.

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Readers interested in historical fiction and diverse narratives.Product leaders and managersReaders interested in historical fiction and diverse cultural narratives.Individuals interested in the intersection of history, mental health, and technology.Readers interested in historical fiction and family narratives.

Books Mentioned

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Best for Readers interested in historical fiction and diverse narratives.Often cited around multi-generational historical fiction

“There's a book called Homegoing, which is about the West Coast of Africa and the impact of the slave trade.”

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Sentiment: Highly Recommended

Trigger: multi-generational historical fiction

For: Readers interested in historical fiction and diverse narratives.

Key quote: “There's a book called Homegoing, which is about the West Coast of Africa and the impact of the slave trade.”

The host mentioned 'Homegoing' as part of a discussion on historical fiction that provides insight into unfamiliar worlds. They emphasized the value of such books in offering perspectives on history and personal experiences that are often overlooked.

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Best for Product leaders and managersOften cited around executive decision making

“It's about change management. They talk a lot about shrinking the change, which is this brilliant idea. If something seems scary and overwhelming, how do you make it so much smaller so that it's an experiment?”

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Sentiment: Deep Dive

Trigger: executive decision making

For: Product leaders and managers

Key quote: “It's not my fault, but it is my problem.”

The host mentions 'Switch' to emphasize the importance of understanding how executives think and make decisions. This book provides insights into influencing behavior and decision-making processes, which is crucial for product leaders.

Amazon search results · affiliate link

Find on Amazon

Best for Readers interested in historical fiction and diverse cultural narratives.Often cited around multi-generational historical fiction

“History of Burning is a book that tells a story of Indian indentured servants that were brought to Uganda.”

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Sentiment: Highly Recommended

Trigger: multi-generational historical fiction

For: Readers interested in historical fiction and diverse cultural narratives.

Key quote: “History of Burning is a book that tells a story of Indian indentured servants that were brought to Uganda to build the British railroad there.”

The host mentioned 'History of Burning' as part of a discussion on multi-generational historical fiction, highlighting its unique perspective on Indian indentured servants in Uganda. This book serves as a valuable window into a lesser-known historical narrative that enriches the reader's understanding of different experiences.

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Pachinko

Best for Individuals interested in the intersection of history, mental health, and technology.Often cited around mental load and AI

“I love this book, Pachinko, that tells the history of a Korean family over several generations.”

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Sentiment: Highly Recommended

Trigger: mental load and AI

For: Individuals interested in the intersection of history, mental health, and technology.

Key quote: “I love this book, Pachinko, that tells the history of a Korean family over several generations.”

The host mentions 'Pachinko' to illustrate the historical context of daily life and the mental load faced by individuals over generations. This comparison highlights the staggering demands of modern life and the potential role of AI in alleviating some of that burden.

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Overstory

Best for Readers interested in historical fiction and family narratives.Often cited around multi-generational historical fiction

“I think the book Overstory is an example of that. It's the story of a family over many generations and around a tree.”

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Sentiment: Passing Reference

Trigger: multi-generational historical fiction

For: Readers interested in historical fiction and family narratives.

Key quote: “I think the book Overstory is an example of that.”

The host mentioned 'Overstory' as an example of multi-generational historical fiction that provides insight into different experiences. They highlighted its thematic connection to family stories and the natural world.

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Homegoing

Lenny's Podcast: Product | Career | Growth · 1:25:45

There's a book called Homegoing, which is about the West Coast of Africa and the impact of the slave trade.

Switch

Lenny's Podcast: Product | Career | Growth · 58:36

It's not my fault, but it is my problem.

History of Burning

Lenny's Podcast: Product | Career | Growth · 1:25:56

History of Burning is a book that tells a story of Indian indentured servants that were brought to Uganda to build the British railroad there.

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Mentioned at 1:25:45

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The host mentioned 'Homegoing' as part of a discussion on historical fiction that provides insight into unfamiliar worlds. They emphasized the valu…

Direct Amazon listing · affiliate link

Mentioned at 58:36

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The host mentions 'Switch' to emphasize the importance of understanding how executives think and make decisions. This book provides insights into i…

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Mentioned at 1:25:56