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

with Jessica Fain

22 Mar 2026 8 min read 1h 5m

TL;DR

Influence isn't manipulation—it's understanding how executives actually think and work. Most product leaders fail because they center themselves rather than practicing curiosity and empathy toward their stakeholders, not realizing executives operate in chaotic calendars with competing pressures and need clear context to make good decisions.

Key Moments

Jessica Fain

“I describe an executive's calendar as like a strobe light going off. You know, you wake up at 8 a.m., you've already got a huge list of urgent things going on. You go from a meeting with finance on a budget to an interview for another executive to a people problem to a legal problem to a product review.”

Explaining why executives often seem disconnected during product reviews and don't have context for your ideas

▶ 7:40

Jessica Fain

“As product managers, one of our best sets of skills is curiosity and empathy and trying to understand our users. But the moment that we're talking to an executive or to a stakeholder, we forget those skills and those talents and we begin to think about our ideas, getting that approval, getting to the next meeting.”

Describing the fundamental mistake product leaders make when pitching to executives

▶ 11:06

Jessica Fain

“Politics is manipulating outcomes in people for your own gain. Influence is about increasing the odds that your good ideas survive.”

Addressing the concern that influence feels icky or manipulative

▶ 13:26

Jessica Fain

“You get paid to have an opinion. You get paid to be a domain expert. And in a lot of ways, your executive is looking for you to be the deepest person in the room, especially if they're good at their job, right? they're looking for you to be the expert.”

Clarifying that successful influence requires strong convictions, not being a yes-person

▶ 16:34

Jessica Fain

“Execs want to be successful, too. They want to be good at their jobs. And how can you help them? I mean, in the best case scenario, your incentives at a local team level or product organization level really closely align with their incentives that you're working on something that really matters to the company.”

Explaining how to reframe pitches around executive success metrics, not just your own priorities

▶ 30:27

About Jessica Fain

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Jessica Fain is a product leader who has held roles at Box, Slack, Brightwheel, and currently Webflow. She's become known for her expertise in influence and executive communication, having served as Chief of Staff to Slack's CPO April Underwood and later to Tamar Huhsua. Her unique perspective on how executives actually make decisions comes from working closely with some of the best product minds in the industry.

Takeaways

Executives are drowning in context-switching Busy executive calendars mean they haven't thought about your problem since you last spoke. You must spend 30 seconds at the start of every meeting resetting context: why are we here, what happened last time, why does this matter to you? This isn't babying them—it's respecting their cognitive load.

Ask better discovery questions, not approval questions Instead of seeking sign-off on your fully-formed idea, approach executives like you would a user discovery interview. Ask what the board is pushing them on, what they're scared of messing up, what pressures they face. Then show how your work helps them win on those fronts.

Show your work by presenting options, not just conclusions Don't lead with one perfect recommendation—present 2–3 options with your reasoning for why you chose yours. This shows you considered alternatives thoughtfully, invites the executive into co-creation, and gives you defensible ground for debate. Keep full working details in an appendix, not the main pitch.