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

Page: https://stenobird.com/podcast/lenny-s-podcast/the-art-of-influence-the-single-most-important-skill-that-ai-can-t-replace-jessica-fain-webflow-ex-slack
Text version: https://stenobird.com/podcast/lenny-s-podcast/the-art-of-influence-the-single-most-important-skill-that-ai-can-t-replace-jessica-fain-webflow-ex-slack.md
Podcast: [Lenny's Podcast: Product | Career | Growth](https://stenobird.com/podcast/lenny-s-podcast)
Published: 2026-03-22T12:31:51+00:00
Episode link: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain
Audio file: https://pscrb.fm/rss/p/api.substack.com/feed/podcast/189787031/e33636fb65141b736d62d710df3bbac6.mp3
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Duration seconds: 5613

## Resource

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 bu…

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## Transcript

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