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Treat Your Exec
Like a User

Jessica Fain
Product leader at Webflow · Fmr. Box, Slack (chief of staff to CPO), Brightwheel
MAR 22 2026
The Thesis

Influence Is How Good Ideas Survive

CURIOSITYEMPATHY(for users)SAME SKILLSFOR EXECS
"Politics is manipulating outcomes for your own gain. Influence is increasing the odds that your good ideas survive."
  • PMs bring curiosity and empathy to users; they forget both the moment they walk into an exec meeting
  • The best PMs treat the exec conversation as a discovery interview, not an approval hunt
  • Annie Pearl gave Jessica the frame: "It's not my fault, but it is my problem"
  • Jessica learned this as chief of staff to April Underwood, then CPO of Slack
Framework

The Executive's Strobe-Light Day

FINANCE / BUDGETEXEC INTERVIEWPEOPLE PROBLEMLEGAL PROBLEMYOUR PRODUCT REVIEW(they haven't thought about you since)
"An executive's calendar is a strobe light going off. They may not have gone to the bathroom today. They have not centered your problems."
  • You've prepped this meeting for weeks; they context-switched into it thirty seconds ago
  • Bring the empathy: help them get into the mindset before you ask for a decision
  • Ask the questions you'd ask a user: "Tell me what the board is pushing you on"
  • Deprioritize things loudly — one of the biggest trust deposits a PM can make
Jessica's ask-back"How strongly do you feel about this? How urgent do you think it is? Do you think that trumps what the team is working on now?" — forces the exec to contextualize, so you're responding to the real signal, not the surface request.
Where Influence Breaks

The Failure Modes
Jessica Sees Most

  • "They just don't get it": if you don't respect the exec, quit. If you do, take their feedback as data
  • Being the yes-person: you get paid to have an opinion, to be the deepest domain expert in the room
  • Going in for approval: that framing pre-loses the meeting. Go in to learn and strengthen your plan
  • Framing rejection as their fault: "You agreed to do something else. That's not them, that's you."
The Noah Weiss notebook

Noah kept a section in his notebook for things he learned from Stuart Butterfield, over years. Not to show off — for his own growth. Later it became the seed of Slack's product principles.

Rubber-stamp trap

Do not treat an exec as a rubber stamp. It fails your product AND fails them. They notice.

Playbook

How Jessica Actually Runs Exec Rooms

  • Ask about their day, their board, their context before you say a word about your plan
  • Bring a real trade-off, not a "we should build something simple." Force the sacrifice out of hiding
  • Deprioritize something out loud — it's how you show you can act like a CPO
  • Then follow up: "How strongly do you feel? Does that trump what my team's doing now?" — and actually respond
The mindset shiftKev at Webflow saw where the org was heading and put a design-review framework in a Loom within an hour — unasked. That is what recognizing an exec's incentives looks like from the outside in.
Contrarian

What Jessica Rejects

✗Influence is playing politicsINSTEAD →✓ Politics manipulates outcomes for personal gain. Influence is doing the work so your good ideas survive.
✗Great work will speak for itselfINSTEAD →✓ Jessica lived this trap; she watched her ideas die on the vine while others got funded. Influence is the delivery mechanism.
✗Killing a project is failureINSTEAD →✓ One of the biggest trust deposits you can make with an exec is deprioritizing things loudly. Do more of that.
✗Say what the leader wants to hearINSTEAD →✓ You are paid to be the deepest domain expert in the room. A yes-person adds no value; that's a failure state execs actively dislike.
Based on Jessica Fain's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTube
GO DEEPER IN THE EPISODE
03:53 Why influence is the highest-leverage skill in product04:47 Why great ideas fail without executive buy-in06:00 How executives actually think09:05 The fundamentals: context-setting, communication, and empathy10:22 Stop pitching for approval, start co-creating with execs12:59 Influence vs. politics (and why people get it wrong)15:44 How to disagree with execs without losing trust17:20 Going in to learn, not to convince19:08 How to present ideas26:05 The Minto-style approach and tailoring your communication to each exec28:22 Why Jessica doesn’t like the question “What’s top of mind for you?”30:24 Understanding incentives to unlock buy-in32:10 Aligning product work with company strategy35:10 Quick summary37:31 Disarming the executive40:49 Speed matters: why fast follow-up builds momentum43:32 How to run high-impact meetings (the 60-second rule)47:00 Why influencing execs is part of your job49:15 Asking for more resources and thinking in 10x bets52:23 What to do when your idea gets rejected54:18 Clarifying information56:50 How to build trust and make ideas stick58:30 Shrinking big ideas into experiments01:02:27 Common mistakes people make when influencing leaders01:06:00 How to grow into your next role01:09:32 How AI is changing influence and product work01:17:55 Using AI to simulate exec feedback and improve pitches01:21:15 Protecting our brains from overwhelm01:22:44 Lightning round and final thoughts
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