Lenny's Podcast: Product | Career | Growth

chevron_right

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

whatshot 2079 snips

Mar 22, 2026

Guest

Jessica Fain

Jessica Fain, a product leader at Webflow and former Slack chief of staff, gets into why great ideas fail without buy-in. She explores how executives make decisions, why the first minute of a meeting matters, and how to disagree without becoming political. They also dig into presenting options, aligning with company strategy, and why AI makes influence even more valuable.

01:33:33

forum

Ask episode

web_stories

AI Snips

view_agenda

Chapters

menu_book

Books

auto_awesome

Transcript

info_circle

Episode notes

question_answer

ANECDOTE

How Chief Of Staff Taught Jessica How Execs Decide

Jessica became chief of staff to learn how executives make decisions after pitching April Underwood while pregnant.
That role revealed how misunderstood executive incentives and calendars are, shaping her influence playbook.

volunteer_activism

ADVICE

Research Exec Preferences And Simulate Their Pushback

Before pitching, learn the exec's priorities and communication preferences from their EA or chief of staff.
Jessica suggests training lightweight GPTs on past reviews to simulate likely pushback and tailor the pitch.

question_answer

ANECDOTE

Customer Love Sprint Rebuilt Slack's Product Craft

To revive product craft at Slack, Jessica launched a two-week 'customer love sprint' where engineers picked fixes to ship.
The sprint shipped 65 improvements and reconnected execs to product quality through a judging event.

Get the Snipd Podcast app to discover more snips from this episode

Why great ideas still die

03:58 • 3min

chevron_right

Executive calendars are strobe lights

07:21 • 3min

chevron_right

Influence is not office politics

10:23 • 5min

chevron_right

Disagree without becoming a yes-person

15:46 • 3min

chevron_right

Research the executive before the meeting

19:10 • 3min

chevron_right

Show options, not just one answer

21:58 • 6min

chevron_right

Ask sharper questions about incentives

28:24 • 7min

chevron_right

Align roadmaps with company strategy

35:18 • 2min

chevron_right

Take the thread and follow up fast

37:33 • 6min

chevron_right

Use the first minute wisely

Influence is part of the PM job

47:02 • 2min

chevron_right

Think in 10x bets and constraints

49:25 • 3min

chevron_right

Create cross-functional pull for big ideas

52:14 • 2min

chevron_right

Build trust through shared context

54:43 • 3min

chevron_right

Shrink risky bets into experiments

57:20 • 5min

chevron_right

Broaden your view to grow senior

01:02:29 • 7min

chevron_right

AI makes influence more valuable

01:09:34 • 8min

chevron_right

Train agents with your product philosophy

01:17:56 • 5min

chevron_right

Influence should still feel authentic

• Mentioned in 25 episodes

Pachinko

Allison Hiroto

Min Jin Lee

This novel follows the story of Sunja, a young Korean woman, and her family as they navigate the challenges of living as immigrants in Japan from the early 1900s to the late 1980s. The book explores themes of love, sacrifice, ambition, and loyalty, set against the backdrop of significant historical events including World War II and the Korean War. It delves into the experiences of discrimination, cultural identity, and the struggles of everyday life for Korean families in Japan.

#901

• Mentioned in 40 episodes

The Overstory

Richard Powers

The Overstory is a sweeping and impassioned work of environmental fiction that follows the lives of nine individuals whose paths are intertwined by their connections to trees. The novel is structured in four parts – 'Roots', 'Trunk', 'Crown', and 'Seeds' – mirroring the parts of a tree. It delves into themes of ecology, climate change, and the interconnectedness of trees and humans, using a blend of science, history, and magical realism. The book advocates for the protection of trees and the natural world, posing critical questions about humanity's relationship with the environment and the long-term consequences of human actions.

#50317

A History of Burning

Janika Oza

Janika Oza's "A History of Burning" traces the journey of an Indo-Ugandan family across four generations, spanning a century of displacement and forced migrations. The novel explores the impact of colonialism, exile, and political instability on the family's identity and resilience. It delves into the complexities of memory, trauma, and the search for belonging across continents. Through vivid storytelling, Oza captures the emotional toll of displacement and the enduring strength of family bonds. The novel's narrative structure mirrors the cyclical nature of the family's experiences, highlighting the enduring power of storytelling in navigating loss and finding a sense of home.

#899

• Mentioned in 40 episodes

Switch

How to Change Things When Change Is Hard

Chip Heath

Dan Heath

In 'Switch', Chip and Dan Heath explore why making lasting changes is difficult due to the conflict between the rational mind and the emotional mind. They present a framework for successful change by uniting these two minds, drawing on decades of research in psychology, sociology, and other fields. The book provides compelling examples of how everyday people have achieved dramatic results by following this pattern, whether in personal, organizational, or societal contexts.

#13336

• Mentioned in 4 episodes

Homegoing

Yaa Gyasi

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