The art of influence: The single most important skill that AI can’t replace

Jessica Fain is a product leader who has worked at Box, Slack, Brightwheel, and now Webflow, including a stint as chief of staff to Slack's CPO. The conversation covers the art and science of influencing executives: understanding how leaders actually make decisions, framing pitches around their incentives, presenting options well, and how AI is changing the skill of influence.

01Key learnings

• Treat stakeholder conversations as discovery interviews: go in to learn and strengthen your plan, not simply to get approval for it.
• Remember executives have chaotic calendars and little context on your topic, so spend under 60 seconds at the start restating why you're meeting and what the goal is.
• Ground your pitch in the executive's success metrics and board pressures, and show explicitly how your proposal moves those outcomes.
• Present more than one option, with the rejected alternatives ready in an appendix, so leaders see you considered the tradeoffs rather than missing them.
• Ask about the reasoning behind opinions you disagree with, and follow subtle hints from executives quickly, since delays cost you their trust and enthusiasm.
• Shrink the change into a small, low-risk experiment with clear checkpoints and failure criteria to build trust before asking for big investment.
• Show strategic thinking by killing or deprioritizing work that doesn't serve company goals; this is one of the strongest trust-building moves.
• In the AI era, the valuable skills are deciding what to build, aligning people around strategy, and building trust, since AI handles much of the synthesis and execution.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.