The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
3/22/20261 hr 34 min
Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.
We discuss:
1. Why great ideas often don’t get buy-in
2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much
3. Why executives are usually optimizing for a global maximum while you are often optimizing locally
4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”
5. Why you should go in to learn, not to convince
6. Why showing only one option is a mistake
7. Why AI will make influence more important, not less
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Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain
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Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0
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Where to find Jessica Fain:
• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Jessica Fain
(03:53) Why influence is the highest-leverage skill in product
(04:47) Why great ideas fail without executive buy-in
(06:00) How executives actually think
(09:05) The fundamentals: context-setting, communication, and empathy
(10:22) Stop pitching for approval—start co-creating with execs
(12:59) Influence vs. politics (and why people get it wrong)
(15:44) How to disagree with execs without losing trust
(17:20) Going in to learn, not to convince
(19:08) How to present ideas
(26:05) The Minto-style approach and tailoring your communication to each exec
(28:22) Why Jessica doesn’t like the question “What’s top of mind for you?”
(30:24) Understanding incentives to unlock buy-in
(32:10) Aligning product work with company strategy
(35:10) Quick summary
(37:31) Disarming the executive
(40:49) Speed matters: why fast follow-up builds momentum
(43:32) How to run high-impact meetings (the 60-second rule)
(47:00) Why influencing execs is part of your job
(49:15) Asking for more resources and thinking in 10x bets
(52:23) What to do when your idea gets rejected
(54:18) Clarifying information
(56:50) How to build trust and make ideas stick
(58:30) Shrinking big ideas into experiments
(01:02:27) Common mistakes people make when influencing leaders
(01:06:00) How to grow into your next role
(01:09:32) How AI is changing influence and product work
(01:17:55) Using AI to simulate exec feedback and improve pitches
(01:21:15) Protecting our brains from overwhelm
(01:22:44) Lightning round and final thoughts
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Referenced:
• Box: https://www.box.com
• Slack: https://slack.com
• Brightwheel: https://mybrightwheel.com
• Webflow: https://webflow.com
• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood
• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua
• Atlassian: https://www.atlassian.com
• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid
• Calendly: https://calendly.com
• Glassdoor: https://www.glassdoor.co.in/index.htm
• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai
• Ethan Eismann on X: https://x.com/eeismann
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield
• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank
• Checkr: https://checkr.com
• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl
• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan
• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief
• Barbara Minto’s website: https://www.barbaraminto.com
• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein
• The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2
• Casa: https://getcasa.com
• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix
• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles)
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Recommended books:
• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927
• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061
• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243
• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.
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Lenny may be an investor in the companies discussed.
To hear more, visit www.lennysnewsletter.com
Clips
Showing 10 of 12Transcript preview
First 90 secondsJessica Fain· Guest0:00
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, we forget those skills and those talents.
Lenny Rachitsky· Host0:11
It's your fault if the leaders didn't buy into your idea.
Jessica Fain· Guest0:14
People completely misunderstand how executives make decisions, what is going on in the heads. I describe an executive's calendar as a strobe light going off. You wake up at 8:00 AM, you've already got a huge list of urgent things going on. They have not had the time, the energy, the wherewithal to center your problems.
Lenny Rachitsky· Host0:34
What are their goals? What are they trying to do? How are they measured? Connect the thing you're pitching them with that success.
Jessica Fain· Guest0:39
There's ways for us to ask much more interesting questions of our executives. Tell me what the board is pushing you on. Execs wanna be successful, too. They wanna be good at their jobs.
Lenny Rachitsky· Host0:50
Sometimes you have the best idea and they just don't buy it.
Jessica Fain· Guest0:52
One of the biggest things you can do to build trust is kill things, deprioritize things. 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 get paid to be a domain expert. Your executive is looking for you to be the deepest person in the room. Bringing your expertise to bear is absolutely crucial. You have to act like a CPO.
Lenny Rachitsky· Host1:16
Today, my guest is Jessica Fain, who's been a product leader at Box and Slack and Brightwheel, and now at Webflow. And she has gotten very, very uniquely good at the art and science of