The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
Lenny's PodcastStewart 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.</p><p></p><p><strong>We discuss:</strong></p><p>1. Why great ideas often don’t get buy-in</p><p>2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much</p><p>3. Why executives are usually optimizing for a global maximum while you are often optimizing locally</p><p>4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”</p><p>5. Why you should go in to learn, not to convince</p><p>6. Why showing only one option is a mistake</p><p>7. Why AI will make influence more important, not less</p><p>—</p><p><strong>Brought to you by:</strong></p><p><a href="https://omni.co/lenny" target="_blank"><strong>Omni</strong></a>—AI analytics your customers can trust</p><p><a href="https://lovable.dev/" target="_blank"><strong>Lovable</strong></a>—Build apps by simply chatting with AI</p><p><a href="https://vanta.com/lenny" target="_blank"><strong>Vanta</strong></a>—Automate compliance, manage risk, and accelerate trust with AI</p><p>—</p><p><strong>Episode transcript:</strong> <a href="https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain" target="_blank">https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain</a></p><p>—</p><p><strong>Archive of all Lenny's Podcast transcripts:</strong> <a href="https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0" target="_blank">https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0</a></p><p>—</p><p><strong>Where to find Jessica Fain:</strong></p><p>• LinkedIn: <a href="https://www.linkedin.com/in/jessica-fain-79b8989" target="_blank">https://www.linkedin.com/in/jessica-fain-79b8989</a></p><p>—</p><p><strong>Where to find Lenny:</strong></p><p>• Newsletter: <a href="https://www.lennysnewsletter.com" target="_blank">https://www.lennysnewsletter.com</a></p><p>• X: <a href="https://twitter.com/lennysan" target="_blank">https://twitter.com/lennysan</a></p><p>• LinkedIn: <a href="https://www.linkedin.com/in/lennyrachitsky/" target="_blank">https://www.linkedin.com/in/lennyrachitsky/</a></p><p>—</p><p><strong>In this episode, we cover:</strong></p><p>(00:00) Introduction to Jessica Fain</p><p>(03:53) Why influence is the highest-leverage skill in product</p><p>(04:47) Why great ideas fail without executive buy-in</p><p>(06:00) How executives actually think</p><p>(09:05) The fundamentals: context-setting, communication, and empathy</p><p>(10:22) Stop pitching for approval—start co-creating with execs</p><p>(12:59) Influence vs. politics (and why people get it wrong)</p><p>(15:44) How to disagree with execs without losing trust</p><p>(17:20) Going in to learn, not to convince</p><p>(19:08) How to present ideas</p><p>(26:05) The Minto-style approach and tailoring your communication to each exec</p><p>(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”</p><p>(30:24) Understanding incentives to unlock buy-in</p><p>(32:10) Aligning product work with company strategy</p><p>(35:10) Quick summary</p><p>(37:31) Disarming the executive</p><p>(40:49) Speed matters: why fast follow-up builds momentum</p><p>(43:32) How to run high-impact meetings (the 60-second rule)</p><p>(47:00) Why influencing execs is part of your job</p><p>(49:15) Asking for more resources and thinking in 10x bets</p><p>(52:23) What to do when your idea gets rejected</p><p>(54:18) Clarifying information</p><p>(56:50) How to build trust and make ideas stick</p><p>(58:30) Shrinking big ideas into experiments</p><p>(01:02:27) Common mistakes people make when influencing leaders</p><p>(01:06:00) How to grow into your next role</p><p>(01:09:32) How AI is changing influence and product work</p><p>(01:17:55) Using AI to simulate exec feedback and improve pitches</p><p>(01:21:15) Protecting our brains from overwhelm</p><p>(01:22:44) Lightning round and final thoughts</p><p>—</p><p><strong>Referenced:</strong></p><p>• Box: <a href="https://www.box.com" target="_blank">https://www.box.com</a></p><p>• Slack: <a href="https://slack.com" target="_blank">https://slack.com</a></p><p>• Brightwheel: <a href="https://mybrightwheel.com" target="_blank">https://mybrightwheel.com</a></p><p>• Webflow: <a href="https://webflow.com" target="_blank">https://webflow.com</a></p><p>• April Underwood on LinkedIn: <a href="https://www.linkedin.com/in/aprilunderwood" target="_blank">https://www.linkedin.com/in/aprilunderwood</a></p><p>• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (ProductMar 22, 20261h 34minListen to full episode
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