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

About this episode

Jessica Fain discusses the art of influence and the nuances of executive decision-making.

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 —…

People in this episode

Host: Lenny Rachitsky

Guest: Jessica Fain

Topics covered

• influence
• executive decision making
• AI impact
• buy-in strategies
• meeting dynamics
• leadership communication

Keywords

• influence
• executive decisions
• AI
• buy-in
• leadership
• communication
• meeting strategies

Sponsors

Omni, Lovable, Vanta

Mentioned in this episode

Organizations: Webflow, Slack

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