The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) - Lenny's Podcast: Product | Career | Growth Recap

Podcast: Lenny's Podcast: Product | Career | Growth

Published: 2026-03-22

Guests: Jessica Fain

What Happened

Jessica Fain, a product leader at Webflow and former chief of staff at Slack, discusses the crucial skill of influence, particularly for product managers. She highlights how product managers often forget the power of curiosity and empathy when communicating with executives, who are often overwhelmed by their packed schedules. Building trust with executives might require deprioritizing certain tasks to align with their goals, which can be more impactful than AI in decision-making.

Fain emphasizes the importance of aligning pitches with executive goals and incentives to secure buy-in for product ideas. The technique of treating executive conversations as discovery interviews can help uncover the reasons behind executive beliefs and decisions. She also notes that influence is not about politics but about increasing the odds that good ideas survive.

Jessica Fain shares insights from her time at Slack, where interactions with executives like Stuart Butterfield and techniques from leaders like Noah Weiss and Elon Frank enriched her understanding of influence. She recommends asking specific questions to better understand executive priorities and suggests that product leaders should not simply agree with executives but should bring their expertise and perspective to the table.

AI is shifting the skill of influence by focusing on deciding which ideas survive and getting stakeholder buy-in rather than just execution. Fain points out that AI tools can be used to analyze past product reviews, aiding in preparation for executive meetings. However, AI cannot replace the human elements of empathy and understanding, which remain crucial in influencing and building trust.

Jessica Fain mentions the concept of 'red teaming', which involves critically assessing one's own ideas from an outsider's perspective to improve them. She stresses the importance of presenting multiple options and using the Minto pyramid principle to effectively communicate recommendations and supporting evidence to executives.

Understanding the pressures and constraints executives face, such as board expectations, can help tailor communication and align team incentives with executive goals. Fain suggests that aligning product work with company goals and user success is crucial for mutual success and influence. Building trust through consistent follow-through on feedback and showing tangible results can also enhance long-term relationships with leaders.

Key Insights