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

What It Covers

Jessica Fain, product leader at Webflow and former Slack chief of staff, breaks down the mechanics of executive influence for product managers. Drawing on direct experience inside Slack's leadership, she explains how executives actually make decisions, why most pitches fail, and how PMs can align their ideas with leadership incentives to build trust and get funded.

Key Questions Answered

• •Executive Calendar Reality: Executives context-switch constantly — moving from budget meetings to legal issues to people problems — and have not thought about your pitch since the last meeting. Counter this by spending the first 30–60 seconds of any meeting re-establishing context: state why you're there, what was decided last time, today's goals, and ask if anything else needs covering. This simple reset dramatically improves the quality of the conversation that follows.
• •Incentive Alignment as Pitch Strategy: Before pitching any idea, map it explicitly to the executive's measurable goals — their OKRs, board pressures, and company-level outcomes. Ask directly what the board is pushing on, or ask their chief of staff or EA what is most urgent for them right now. Then structure your pitch to show how your proposal accelerates their specific success criteria, not just your team's local metrics or feature delivery targets.
• •Present Three Options, Not One: Bringing a single recommendation to an executive review signals that alternatives were not considered, which erodes confidence. Present three options with the preferred solution in the middle — a classic Goldilocks structure. This demonstrates analytical rigor, preempts the objection that something was missed, and gives the executive a framework for discussion rather than a binary approve-or-reject decision on one path.
• •Curiosity as Disarming Tactic: When an executive says something that contradicts your data or expertise, respond with "That's so interesting — what led you to believe that?" rather than defending your position. This question surfaces the reasoning, board pressure, or recent experience behind their view, enabling co-creation rather than confrontation. It also signals respect for their domain knowledge, which builds the trust needed for future pitches on harder or more novel ideas.
• •Kill Things to Build Trust: One of the fastest ways to establish credibility with senior leaders is to proactively deprioritize or kill initiatives that are not working, rather than defending them. This signals that your incentives are aligned with company outcomes, not personal scope protection. Pair this with pre-defined success criteria — tell the executive upfront how you will know if something is failing and on what date you will return with a go/no-go decision.
• •Shrink the Change for Novel Ideas: When pitching net-new or high-risk ideas that lack executive buy-in, reduce the perceived investment to a two-week proof of concept or a single experiment with defined success metrics. The book *Switch* frames this as "shrinking the change." Ask the executive directly what failure would look like for them, then design the experiment to address that specific risk. Momentum from a small win creates the credibility needed to fund the larger version.
• •AI Shifts PM Value to Influence and Strategy: As AI handles data analysis, note-taking, and code generation, the highest-leverage PM skill becomes deciding what to build and aligning others around that decision. Use AI tools practically: train a GPT on past product review transcripts to simulate executive pushback before a meeting, run PRDs through Claude to identify weak data or thin UX reasoning, and use Slackbot to surface what topics a leader has been focused on recently.