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

Q: Jessica Fain argues executives optimize for a global maximum while PMs optimize locally, making ince

Jessica Fain argues executives optimize for a global maximum while PMs optimize locally, making incentive alignment the key to getting buy-in.

Q: As AI automates analytical work, human influence skills become more valuable, not less, making them

As AI automates analytical work, human influence skills become more valuable, not less, making them the PM skill most worth developing.

Lenny's Newsletter·Sunday, March 22, 2026·3 min read

Product Business AI/ML

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AI Summary

Lenny Rachitsky interviews Jessica Fain, product leader at Webflow and ex-Chief of Staff to the CPO at Slack, on the art of influencing executives. Fain shares tactical frameworks for getting buy-in, including aligning with executive incentives, presenting multiple options rather than one, and entering meetings to learn rather than convince. She argues that as AI automates more analytical work, human influence skills become increasingly valuable and irreplaceable.

Key Facts

✓Jessica Fain argues executives optimize for a global maximum while PMs optimize locally, making incentive alignment the key to getting buy-in.

✓Presenting only one option to executives is a tactical mistake — always bring three options to create a real decision framework.

✓As AI automates analytical work, human influence skills become more valuable, not less, making them the PM skill most worth developing.

Author Takes

BullishLenny's Newsletter

AI and influence skills

AI will make human influence skills more important, not less, as analytical tasks get automated and relationship-driven decision-making becomes the differentiator.

BearishLenny's Newsletter

Presenting a single option to executives

Showing only one option to an executive is a mistake because it removes their agency and signals a lack of strategic thinking.

Contrarian Angle

Go In to Learn, Not to Convince

Jessica Fain's counter-intuitive approach to executive meetings: enter with the goal of understanding the executive's perspective rather than selling your idea, which paradoxically increases your chances of getting buy-in.

Most PMs enter executive meetings in persuasion mode; Fain argues this is exactly backwards and kills credibility.

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