Lenny's Podcast: Product | Career | Growth

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

March 22, 2026

AI Summary

5 min read

Jessica Fain, a product leader at Webflow with prior roles at Slack, Box, and Brightwheel, explains influencing executives as a pivotal skill for product managers. Drawing from her time as chief of staff to Slack CPOs April Underwood and Tamar Yoshiyahu, she describes how misunderstanding executives' decision-making leads to failed ideas, even strong ones rooted in user insights. Influence, she argues, channels curiosity and empathy—core PM strengths—toward leaders, ensuring ideas gain traction amid their chaotic schedules.

Executives' Overlooked Realities

Executives operate in a "strobe light" calendar of constant context-switching: budget meetings, interviews, legal issues, and people problems, often without time for basics like bathroom breaks. They enter product reviews unprimed, focused on global company optima rather than a PM's local priorities. Fain stresses applying user empathy here—execs want success too, measured by board pressures, OKRs, or revenue goals. Instead of centering your pitch, connect it explicitly: "How does this improve the metric you're responsible for?" Probe deeper with questions like "What is the board pushing you on?" or "What pressures are you facing?" rather than generic "What's top of mind?" This uncovers incentives, as PMs often forget their discovery skills when seeking approval.

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What you'll learn

1 (00:00) **🎙️ Introduction: Jessica Fain**
2 (04:00) **Why Influence is Crucial for Product Success**
3 (05:45) **Understanding Exec Decision-Making and Calendars**
4 (08:30) **Setting Context and Helping Execs Engage**
5 (11:47) **Approach Meetings to Learn, Not Just Approve**
6 (13:00) **Influence vs. Politics: Focus on Empathy and Learning**
7 (16:03) **Handling Disagreement: Bring Domain Expertise**

+ Full timestamped outline available in the app

Show Notes

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

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