Lenny's Podcast: Product | Career | Growth
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PodcastLenny's Podcast: Product | Career | Growth
Publisher/creatorLenny Rachitsky
Shortcast updated
About this episode
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 — Brought to you by: Omni —AI analytics your customers can trust Lovable —Build apps by simply chatting with AI Vanta —Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jessica Fain: • LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — 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 — 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) — 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 — Production and marketing by https://penname.co/ . For inquiries about sponsoring the podcast, email [email protected] . — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com
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Episode summary
Today we’re digging into the art and science of influence with Jessica Fein, a product leader from Box, Slack, Brightwheel, and now Webflow, and why this single skill can change your career.
Influence is how great ideas survive; executives live in nonstop context-switching, so help them reset with a crisp 30-second why-we’re-here and bring empathy to how they think and decide.
A lot of us hope great work speaks for itself, then hit a wall; what actually gets leaders to buy in?
When I moved from PM to chief of staff at Slack, I learned people misread executive incentives and calendars; treat leaders like users, stay curious about what drives them, and adopt the mindset of it’s not my fault, but it is my problem.
Some hear “influence” and think politics; how do you make this feel clean and useful?
Politics is manipulation for personal gain; influence is raising the odds that good ideas live by learning, testing, and reflecting leaders’ principles back to them without ego.
How do you push back on a leader and keep the room with you—any phrases that work?
Bring real domain depth and ask, that’s interesting—what led you to believe that, then co-create from their inputs while calmly testing their confidence with data and customer proof.
What prep gives you an edge, and how do you present to different exec styles?
Ask their EA, chief of staff, and past pitchers what lands, use AI to spot likely pushbacks and your blind spots, align early with office hours, show a clear recommendation plus viable options, and match their preferred format and cadence.
Is asking what’s top of mind still useful, and how do you align with incentives?
Skip the bland top-of-mind and ask spicier prompts like what’s the board pressing you on and what will success look like, then tie your plan to company goals; at Slack we ran a customer-love sprint to restore craft because leadership believed that was our edge.
How do you keep meetings tight and follow subtle breadcrumbs leaders drop?
Open with a 30-second agenda, clarify urgency with how strongly do you feel about this and does this displace current work, and after a silent read, surface only the hot topics that need live debate.
What does showing up like a CPO look like in practice?
State what’s possible now and paint the 10 times path with explicit asks for people, time, and cross-functional help, then follow up fast so momentum—and executive attention—doesn’t evaporate.
If your big idea isn’t landing, how do you build trust and traction?
Prototype a scrappy version and build a cross-functional groundswell, synthesize the leader’s instincts on a whiteboard into actionable frames, deliver results, shrink the change into safe experiments with check-in dates, and be willing to kill weak bets.
What do ambitious PMs miss about thinking like senior leaders?
Executives carry broader context, so ask what they know that you don’t, expand your view to the whole business, practice product citizenship, tell a clear company story for your work, and recommend stopping low-leverage efforts.
How is AI changing influence and where do humans still matter most?
Execution is speeding up, so judgment, alignment, distribution, and trust are the leverage; treat agents like junior teammates by encoding your product philosophy, setting guardrails, inviting them to stress-test plans, and using them to protect focus in a world of overwhelm.
Lightning round—book recs?
Multi-generational historical fiction like Pachinko, Homegoing, and A History of Burning; they’re powerful windows into lives and histories I didn’t know.
Recent show and favorite product?
I’m hooked on an intense kitchen-world series for its craft and grit, and I love two simple joys: a towel warmer and CASA’s household assistant service.
A motto you live by and a favorite poster behind you?
First the guests keeps us oriented to service and kindness, and a Jimi Hendrix at the Greek poster reminds me why music and Berkeley feel like home.
Where can folks find you, and thanks for joining us.
Find me on LinkedIn, and tell me what resonated and how you’re applying these ideas so we can support each other through this change.
Thanks for listening; subscribe on your favorite app, drop a rating or review, and find past episodes at Lenny’sPodcast.com.
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