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

Jessica Fain frames influence as a product skill rather than office politics. Product managers already use curiosity and empathy to understand users, but often abandon those habits when speaking with executives. Her account of ideas at Slack that either received funding or “died on the vine” led her to become a chief of staff and study how executive calendars, incentives, and context shape decisions. The practical implication is that a strong idea is not enough: the person presenting it must help a stakeholder understand why it matters in the stakeholder’s own world.

Executive meetings often begin with a severe context mismatch. A product manager may prepare for weeks while an executive arrives from finance, hiring, legal, and people issues. Fain recommends using the first 30 seconds to explain why the meeting exists, what changed since the last conversation, why the topic matters, and how the meeting will run. The presenter should also adapt the format to the executive’s communication style and use the executive as a key user: learn whether that person responds to design, customer stories, dashboards, experiments, a document, or quiet reading time.

The goal should be learning and improving the plan, not merely obtaining a rubber stamp. Fain’s maxim, “It’s not my fault, but it is my problem,” shifts responsibility from blaming a leader to understanding the conditions that produced a decision. She argues that this approach is not manipulation when it is genuine: the executive contributes domain expertise and context, while the product leader protects user understanding and product judgment. The approach fails when the presenter neither respects the stakeholder’s expertise nor asks questions that reveal it.