The Art of Executive Influence
Jessica Fain, product leader at Webflow and former chief of staff and PM at Slack, unpacks the art of influence — the single highest-leverage skill for product leaders outside of AI. Drawing from her experience working alongside Slack CPOs April Underwood and Tamar Yehoshua, she reveals how executives actually make decisions and why most PMs fail to get buy-in. Her core message: influence isn't politics — it's increasing the odds that your good ideas survive by treating your executive like your most important user.
The talk itself: youtube.com/watch?v=RP4vJeIb7WU
Influence separated from politics in a way you can act on, from someone who ran a chief-of-staff function at Slack. The strobe-light description of an executive's calendar is worth the first ten minutes alone.
The argument, in 8 sections
10 quotes, none repeated01The Executive's Strobelight Calendar
The single biggest mistake PMs make is misunderstanding what it's like inside an executive's day. While the PM has spent two to six weeks preparing for a product review, the executive coming into that session hasn't thought about you since the last meeting. They may not have gone to the bathroom today. Fain's metaphor is vivid: “I describe an executive's calendar as like a strobe light going off. You wake up at 8 a.m., you've already got a huge list of urgent things going on.” They go from a finance budget meeting to an interview for another executive, to a people problem, to a legal problem, to a product review — all in one morning.
The fix is disarmingly simple: take 30 seconds at the top of every meeting to reorient them. “We're here to discuss X. Last time we met, we left it off here. The goals of today's meeting are Y. Here's how we're going to run this meeting.” Then stop talking. Add: “Was there anything else you were hoping to cover today?” This tiny investment pays enormous dividends because it helps the executive center on your problem rather than the dozen other emergencies competing for their attention. As Fain puts it, “they have not had the time, the energy, the wherewithal to center your problems.”
“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.”
The single most vivid metaphor for why executives struggle to center on your ideas — and why 30 seconds of context-setting changes everything.
02Influence Is Not Politics — It's Learning
Fain draws a sharp line between politics and influence. “Politics is manipulating outcomes in people for your own gain. Influence is about increasing the odds that your good ideas survive.” The key reframe: PMs are world-class at curiosity and empathy when it comes to understanding users, but “the moment that we're talking to an executive or to a stakeholder, we forget those skills and those talents.”
Instead of going into a meeting seeking approval for your plan, go in to learn. Ask: “How can I strengthen this plan using the domain expertise, context, and experience this person brings?” The result is twofold: the executive feels like you've built the product alongside them, and you end up with a better product. Fain's litmus test: if you don't respect the person, if you don't believe they know something you don't, you need to quit and work somewhere else. But if you respect them, take the feedback, ask questions, and don't treat the meeting as a rubber stamp. “That's a failure state and it's a failure state that they don't like.”
Noah Weiss, Slack's former CPO, embodied this perfectly: he kept a small notebook of things he learned from Stewart Butterfield over the years — not to show off, but for “genuine learning and growth of his own ideas and place as a product leader.” See also: consume/concepts/protect-your-thinking, consume/concepts/judgment-human-advantage.
“Politics is manipulating outcomes in people for your own gain. Influence is about increasing the odds that your good ideas survive.”
Reframes influence from something icky to something essential — it's the mechanism by which great products get built.
03Align Your Pitch with Their Incentives
Executives are optimizing for a global maximum, not the local maximum you're optimizing for. The question isn't “what's top of mind for you?” — a question Fain argues has lost its firepower and become a trope. Instead, ask spicier questions: “Tell me what the board is pushing you on.” “What pressures are you facing?” “What are you really scared about messing up?”
Execs want to be successful too. They want to be good at their jobs. So understand what their success looks like — their OKRs, the board pressures, the metrics they're measured on — and explicitly connect your pitch to that success. Fain demonstrated this at Slack with the “customer love sprint,” where she aligned a two-week bug-bash sprint with the executive team's concern that Slack had lost its product-craft mojo. By framing it as restoring a key differentiator, she got buy-in, shipped 65 improvements, and brought executives into the judging process. See also: consume/concepts/founder-mode-as-leverage.
“What are the success criteria for an exec and how do you model your world to amplify that success so that both of you can be more successful.”
04Present Options, Hold the Whiteboard
Two common errors when pitching executives: trying to prove you did your homework by overwhelming them with process (“we talked to 16 participants from 15 geos”), and presenting only one recommendation. Fain learned the first one the hard way — the person she was trying to convince “glazed over, got on their phone, and I totally blew the meeting.” Put the evidence in the appendix. The baseline expectation is that you did your job.
For the second error: present at least three options, with the Goldilocks recommendation in the middle. This shows you considered alternatives and preempts the “did you think of X?” objections. When her CPO Rachel Wolan pushed back on a single-option strategy doc, Fain's team turned around a new doc in two days showing all the options they'd considered and why each wouldn't serve the outcomes. Once the CPO saw the permutations, she said: “Oh yeah, okay. I see why the solution that you're proposing makes the most sense.”
April Underwood's technique was holding the whiteboard marker in strategy meetings — extracting Stuart Butterfield's instincts and packaging them into actionable frameworks in real time, co-creating rather than just pitching. See also: consume/concepts/make-the-decision-70-percent.
“The baseline expectation is that you did your job and that this is built on a solid foundation of your domain expertise.”
05Follow the Subtle Threads — Speed Matters
Executives rarely give clear-cut asks like “write a brief on exactly this thing.” More often, the feedback is subtle: “I wonder if...” or “Have you considered...?” The best people take the bait. Fain calls these “breadcrumbs of opinions” and observes that most PMs let them pass — and the executive loses faith that you'll follow up on what they believe is important.
At Slack, Tamar Yehoshua asked four times across multiple strategy reviews for “the top 10 use cases on X.” By the fourth time, she was visibly frustrated. The team hadn't picked up on the cue that there was something deep underneath — an important piece of feedback they weren't pulling on. The antidote: act fast. When Rachel Wolan at Webflow said “we're going to have to think about design reviews at some point,” the head of design had a Loom with a full framework ready within an hour. Speed signals that you're listening and that you can be trusted.
A clarifying question to use when you're unsure: “How strongly do you feel about this?” It surfaces whether it's a random idea, a suggestion, or a mandate. See also: consume/concepts/reward-learning-not-outcomes.
“A lot of times I see people don't take that invitation from the executive to actually engage on the subtle feedback they're giving.”
06Kill Things to Build Trust
One of the most counterintuitive trust-building moves: kill things. Deprioritize. “If you're thinking about how do you be more senior, how do you show up in a way that is in a leadership mindset, you have to act like a CPO.” Killing a project you've invested months in because it's not working demonstrates that you share the executive's incentives — you're optimizing for company and user outcomes, not your own ego.
Fain also recommends “shrinking the change” (from the book Switch): turn a scary six-month project into a one-week proof of concept. This reduces the perceived risk, builds momentum through quick wins, and creates a track record that enables you to return later with the bigger, scarier ask. And when outcomes are uncertain — especially with AI-native products — provide certainty about the check-in point: “I don't know if this is going to be successful. I'm going to check in with you on X date.”
“One of the biggest things you can do to build trust is kill things, deprioritize things. That is a very very senior way of thinking.”
The most unexpected trust-building tactic — shows you optimize for the company, not your own ego.
07AI Makes Influence the 10x Skill
Fain believes we are entering “a golden age of product management, not of product managers, but of product management.” As execution complexity plummets and everyone can build, the leverage shifts from doing the work to deciding what work survives. PMs who built careers on being the best notetaker, the Gantt chart master, or the data analyst will find that AI is better at all of those things. What's left — and what's 10x more important — is influence, stakeholder management, and learning.
AI can't yet be an anthropologist. The best product thinkers get to novel insights through user empathy and deep understanding of business dynamics, then bring people along for the ride. Fain also notes that as ideas proliferate and building accelerates, mistakes compound faster too. Strategy clarity becomes the essential anchor — it's what lets teams run at maximum velocity without building the wrong things. In a world of AI agents as colleagues, influence becomes bidirectional: you're teaching agents your product philosophy so they can in turn influence you effectively. See also: consume/concepts/need-more-pms-not-fewer, consume/concepts/taste, consume/concepts/narrow-specialization-decline.
“The act of influence, the act of stakeholder management, the act of learning is the 10x skill.”
In an AI world, influence isn't a soft skill — it's the hardest and highest-leverage one.
08Authenticity Is Your Superpower
Fain closes with a personal note: she received early-career feedback to “show up more like a man would” — more aggressively, more decisively. It took her years to realize that “who I am and how I show up is actually my superpower that I can double down on.” You don't need to be an extrovert or a people person to build influence. Any personality type — shy, introverted, data-oriented, technical — can build trust and influence in a way that feels authentic. What matters is knowing what you want to accomplish and growing into it in a way that's true to you. See also: consume/concepts/inner-voice.
“Who I am and how I show up is actually my superpower that I can double down on. And I don't need to be like someone else.”
Influence isn't reserved for extroverts or natural politicians — authenticity is the real foundation.
Also worth keeping
2 more · each links to its minute“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.”
This is the core diagnosis — PMs have the right skills but apply them to the wrong audience.
“We are entering a golden age of product management, not of product managers, but of product management.”
When execution becomes commoditized, the skills of deciding what to build and bringing people along become the real differentiator.
What to take away
5 lines- 01Spend 30 seconds framing every exec meeting
Before diving in, state why you're there, what happened last time, and the meeting's goals. Then ask if they wanted to cover anything else. This tiny ritual makes the difference between a confused executive and an engaged one.
- 02Replace “what's top of mind?” with spicier questions
Ask about board pressures, what they're scared of messing up, and what success looks like for them. Then explicitly connect your pitch to that success — make it impossible for them to say no because your idea directly serves their goals.
- 03Present three options, not one
The Goldilocks structure shows you've done the thinking, preempts objections, and turns the conversation from “should we do this?” to “which of these is best?” Keep the appendix ready with the evidence, but don't lead with it.
- 04Respond to subtle executive feedback within hours, not weeks
When an exec says “I wonder if...” or “have you considered...”, take the bait immediately. Speed of follow-up signals you're listening and builds the trust needed for the next, bigger ask.
- 05Kill something this quarter
Voluntarily deprioritize a project that isn't working and explain why. This demonstrates you think like a CPO — optimizing for company outcomes over personal territory — and is one of the fastest ways to earn an executive's trust. ---