Jessica Fain (Webflow, ex-Slack)22 March 2026

The art of influence: The single most important skill that AI can’t replace

7Frameworks

14Insights

Episode overview

Jessica Fain explains that influence is essential to building products because good ideas require stakeholder commitment, resources, and momentum. She offers practical methods for influencing executives: understand their incentives and context, adapt to their communication style, lead with a recommendation, invite genuine learning, and respond quickly to feedback. The conversation also examines how AI makes execution cheaper while increasing the value of strategy, judgment, trust, and the ability to align people around what should be built.

Key ideas

Treat executives like users: apply curiosity and empathy to their goals, pressures, incentives, calendar, and preferred communication style.
Open executive meetings with a sub-60-second reset covering why the group is there, what happened previously, today’s goals, and any additional agenda needs.
Lead with a recommendation and show a small set of meaningful alternatives, while keeping deeper evidence and discarded options available in an appendix.
Enter discussions to learn and co-create, using questions such as “What led you to believe that?” to uncover information and assumptions you lack.
Connect proposals and team metrics directly to company outcomes, executive success criteria, user value, and current strategic priorities.
Build trust by acting on feedback, delivering results, shrinking risky changes into experiments, defining checkpoints, and willingly killing weak initiatives.
Think like a CPO by broadening beyond a local feature or team, identifying constraints leaders can remove, and prioritizing the overall company outcome.
As AI reduces execution costs, durable product leverage shifts toward strategic clarity, novel user insight, judgment, trust, distribution, and organizational influence.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Influence4 steps

Anchor the Pitch to the Exec's Incentives

Find the metric, OKR, or board pressure they own, then show how your idea moves it.

Read →

Leadership3 steps

Follow the Breadcrumbs and Calibrate Urgency

Act fast on an exec's subtle hints, but ask how strongly they actually feel first.

Read →

Influence3 steps

Shrink the Change to Build Trust

De-risk a scary idea into a two-week experiment with a fixed check-in date.

Read →

Communication3 steps

Stewart Plus Two More

Never bring one option; show a Goldilocks three and hold the rest in the appendix.

Read →

Communication4 steps

The 60-Second Meeting Reset

Buy a context-starved exec 30 seconds of orientation before you pitch.

Read →

Communication3 steps

Themes for Discussion at the Top of the Doc

Bubble up the spiciest 3 topics live; answer the hundred nitpicks offline.

Read →

Influence4 steps

Treat the Executive as Your Key User

Run stakeholder conversations as discovery interviews, not approval requests.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 15

Jessica FainMentionsToday my guest is Jessica Feain who's been a product leader at Box and Slack and Brightitewheel and now at Webflow
“Jessica, thank you so much for being here. Welcome to the podcast.”
▶ Watch at ~3:30approx.
Tamar YehoshuaMentionsTamar is currently president of product and Technology at glean
“is now a CPO and head of AI at Atlassian.”
▶ Watch at ~6:30approx.
Tamar YehoshuaMentionsTamar is currently president of product and Technology at glean
“was later chief of staff to Tamario Hoshua. Um, who succeeded succeeded April”
▶ Watch at ~6:30approx.
Annie PearlCoinedAnnie is currently Chief product officer at calendly before that she was Chief product officer at Glassdoor
“Annie Pearl who was my first PM manager back at Box.”
▶ Watch at ~10:30approx.
Annie PearlCoinedAnnie is currently Chief product officer at calendly before that she was Chief product officer at Glassdoor
“She always said to me, "It's not my fault, but it is my problem."”
▶ Watch at ~10:30approx.
Noah WeissMentionsNoah is Chief product officer at slack where he spent the last seven years
“Noah Weiss who succeeded um uh Tamario Suez, CPO of Slack”
▶ Watch at ~14:00approx.
Stewart ButterfieldMentionsStewart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time.
“I actually have a section of this notebook that I've been keeping things I learned from Stuart over the years.”
▶ Watch at ~14:30approx.
Ali RaylCoinedearly Slack employee
“Ali Rail early Slack employee implemented something called hey Stuart what do you think”
▶ Watch at ~21:00approx.
Rachel WolanMentionsour CPO
“we had a recent product review with my manager Rachel Woolen.”
▶ Watch at ~23:30approx.
Stewart ButterfieldCoinedStewart founded Flickr and then Slack, which he sold to Salesforce in one of the biggest acquisitions in tech history at the time.
“we called it Stuart plus two more.”
▶ Watch at ~25:30approx.
Barbara MintoCoinedthe first female consultant at McKenzie or something like that
“there's this uh lady Barbara Mento.”
▶ Watch at ~26:30approx.
Rachel WolanMentionsour CPO
“Rachel our CPO said you know hey Kev our head of design”
▶ Watch at ~39:00approx.
Jeff WeinsteinMentionsJeff was the product lead for Stripes payment infrastructure teams where helped scale stripe payments to hundreds of billions of dollars
“The epitome of this to me is Jeff Weinstein, I think is how I pronounce his last name, or Weinstein at Stripe.”
▶ Watch at ~1:06:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“I want you to do a whole episode on distribution because I feel this so much.”
▶ Watch at ~1:14:00approx.
Jimi HendrixMentionsan incredible musician
“my favorite one is probably, uh, Jimmyi Hendris plays the Greek.”
▶ Watch at ~1:31:00approx.

Resources · 40

WebflowMentionssoftware · Webflow
“been a product leader at Box and Slack and Brightitewheel and now at Webflow”
▶ Watch at ~1:00approx.
BrightwheelMentionscompany
“been a product leader at Box and Slack and Brightitewheel and now at Webflow”
▶ Watch at ~1:00approx.
Lenny's NewsletterMentionsnewsletter · Lenny Rachitsky
“available exclusively to Lenny's newsletter subscribers.”
▶ Watch at ~2:00approx.
OmniRecommendssoftware · Omni
“check out omni.co/lenny for a free 3we trial.”
▶ Watch at ~2:30approx.
LovableUsessoftware · Lovable
“I use it regularly and I could not recommend it more highly.”
▶ Watch at ~3:00approx.
LovableRecommendssoftware · Lovable
“Get started for free at lovable.dev.”
▶ Watch at ~3:30approx.
SlackMentionssoftware · Slack Technologies
“I was a PM at Slack.”
▶ Watch at ~5:00approx.
AtlassianMentionscompany
“is now a CPO and head of AI at Atlassian.”
▶ Watch at ~6:30approx.
Google CalendarMentionssoftware · Google
“A lot of times on Google calendar, it's blocked.”
▶ Watch at ~7:30approx.
GlassdoorMentionscompany · Glassdoor
“a former CPO at Calendarly and Glass Door and now at Microsoft”
▶ Watch at ~10:30approx.
BoxMentionscompany
“Annie Pearl who was my first PM manager back at Box.”
▶ Watch at ~10:30approx.
MicrosoftMentionscompany · Bill Gates and Paul Allen
“and now at Microsoft and Annie's just the best.”
▶ Watch at ~10:30approx.
CalendlyMentionssoftware · Tope Awotona
“a former CPO at Calendarly and Glass Door and now at Microsoft”
▶ Watch at ~10:30approx.
SlackbotUsessoftware · Slack
“You can ask Slackbot, "What has Rachel been posting about lately? What what do you think is most important to her?"”
▶ Watch at ~19:30approx.
GPTUsessoftware · OpenAI
“A colleague of mine, a peer on on our product leadership team trained a GPT on a bunch of um transcripts”
▶ Watch at ~20:00approx.
ClaudeRecommendssoftware · Anthropic
“Cloud's amazing for this.”
▶ Watch at ~20:30approx.
FigmaUsessoftware · Figma
“Have them in an appendix, have them in a draft Figma file, whatever it is.”
▶ Watch at ~25:00approx.
Minto Pyramid PrincipleRecommendsother · Barbara Minto
“Have you have you ever looked into the Mento pyramid way of presenting stuff?”
▶ Watch at ~26:00approx.
LoomUsessoftware · Loom
“Kev had had a loom put together of, hey, here's a framework of high-risisk design changes”
▶ Watch at ~39:00approx.
VantaMentionssoftware · Christina Cacioppo
“That's where Vanta comes in. Vanta helps companies of all sizes get compliant fast”
▶ Watch at ~46:00approx.
SwitchRecommendsbook · Chip Heath and Dan Heath
“one of the only business books I've ever liked is called Switch.”
▶ Watch at ~58:30approx.
StripeMentionscompany · Patrick Collison and John Collison
“The epitome of this to me is Jeff Weinstein, I think is how I pronounce his last name, or Weinstein at Stripe.”
▶ Watch at ~1:06:00approx.
SalesforceMentionscompany · Salesforce
“If everyone thinks they can build the next Salesforce on their own, by the way, I don't believe that.”
▶ Watch at ~1:14:00approx.
GeminiMentionssoftware · Google
“the quintessential example we've seen here is with Gemini and Google's tools”
▶ Watch at ~1:14:00approx.
CodexUsessoftware · OpenAI
“I just find codeex and clock code are so good at actually giving you ideas for what to build.”
▶ Watch at ~1:15:30approx.
PachinkoRecommendsbook · Min Jin Lee
“I love this book um Pachenko that tells the history of um a Korean family over several generations.”
▶ Watch at ~1:21:30approx.
HomegoingRecommendsbook
“there's a book called Homegoing, which is about the west coast of Africa and the impact of the slave trade”
▶ Watch at ~1:25:30approx.
The OverstoryRecommendsbook
“I think the book overstory is an example that.”
▶ Watch at ~1:26:00approx.
A History of BurningRecommendsbook
“history of burning is a is a book that tells a story of um Indian indentured servants”
▶ Watch at ~1:26:00approx.
The PittRecommendstv show
“I have been obsessively watching The Pit”
▶ Watch at ~1:26:30approx.
AmazonUsescompany · Jeff Bezos
“It was like 35 bucks on Amazon and it has led to so much joy in our household.”
▶ Watch at ~1:27:30approx.
KasaUsescompany
“I've been a loyal user of Casa”
▶ Watch at ~1:28:00approx.
KasaRecommendscompany
“I'm really excited to see them see them thrive.”
▶ Watch at ~1:28:30approx.
KasaMentionscompany
“I was looking up their domain name, getcasa.com.”
▶ Watch at ~1:29:00approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“one of the core values at Airbnb was be a host.”
▶ Watch at ~1:30:30approx.
LinkedInUseswebsite · LinkedIn
“the main place I am online is on LinkedIn.”
▶ Watch at ~1:32:00approx.
The Greek Theatre at UC BerkeleyRecommendsplace
“Should everyone should go. It's such a fun spot. Right. right on UC Berkeley's campus.”
▶ Watch at ~1:32:00approx.
Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“You can find all past episodes or learn more about the show at lennispodcast.com.”
▶ Watch at ~1:33:00approx.
Apple PodcastsRecommendssoftware · Apple Inc.
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
▶ Watch at ~1:33:00approx.
SpotifyRecommendssoftware · Spotify
“you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app.”
▶ Watch at ~1:33:00approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster13:00

Influence Isn't Politics: Reframing the 'Icky' Feeling

Jessica pushes back on the idea that working on influence is manipulative or political. She draws a hard line: politics is manipulating people for your own gain, while influence is just raising the odds your good ideas survive. Treat stakeholder conversations as discovery interviews to strengthen your ideas, not as politicking.

Politics manipulates outcomes for personal gain; influence increases the odds good ideas survive
People let ego and their own narrative get in the way of empathy
Treat stakeholder conversations as discovery interviews to strengthen ideas
Done in a genuine, low-ego way, this is learning, not manipulation

“Influence is about increasing the odds that your good ideas survive.”
Jessica Fain · 13:30

#influence#office-politics#mindset#product-management

Hot Take· 3

Hot Take29:00

Hot Take: Stop Asking Execs 'What's Top of Mind for You?'

Jessica argues the 'what's top of mind' question has lost its firepower because it's become a generic, neutralized frame execs answer on autopilot. Like a good user researcher, you should ask sharper, more emotional questions that reveal what someone is actually scared of or pressured by. She asks her own CEO what the board is pushing them on, since even a CEO has a boss.

'What's top of mind' has become a trope that produces generic, neutralized answers
Instead ask 'What's the most urgent priority you're scared of messing up?'
Ask a CEO what the board is pushing them on — everyone has a boss
Get at the emotion and drive behind the priority, not the sanitized version

“I will tell you I am not a big fan of the what's top of mind for you uh question this a hot take because…”
Jessica Fain · 29:00

#influence#questions#executives#hot-take

Hot Take1:00:30

The Best Way to Build Trust Is to Kill Things

Counter to the instinct to always grab more resources and ship more features, Jessica argues that killing or deprioritizing your own projects is one of the strongest trust-building moves. It signals a senior, company-first mindset aligned with the executive's concern for the overall outcome. Pair it with clear criteria for how you'll know something isn't working and when you'll come back with a decision.

Killing or deprioritizing work signals a senior, company-first mindset
It aligns you with the exec who cares about the whole company and user outcome
Counters the default instinct to acquire more resources and features
Pair it with 'here's how I'll know it's not working' and a check-in date

“I think one of the biggest things you can do to build trust is kill things, deprioritize things.”
Jessica Fain · 1:00:30

#influence#trust#prioritization#seniority

Hot Take1:09:30

AI Ushers In a Golden Age of Product Management (Not Product Managers)

Jessica argues AI makes execution cheap, so the leverage shifts from doing the work to deciding what work survives and getting people bought in. As everyone becomes a builder, the type-A Gantt-chart-and-notetaking version of PM loses value while influence, stakeholder management, and learning become the 10x skills. She frames it as a golden age of product management as a craft, even if not of the PM job title.

Execution complexity is plummeting and everyone can be a builder
Leverage shifts from doing the work to deciding what work survives
The Gantt-chart-master, best-notetaker version of PM loses value to AI
Influence, stakeholder management, and learning are the 10x skills

“we are entering a golden age of product management, not of product managers, but of product management”
Jessica Fain · 1:09:30

“the act of influence, the act of stakeholder management, the act of learning is the 10x skill.”
Jessica Fain · 1:11:30

#ai#product-management#influence#future-of-work

Explainer· 2

Explainer07:30

Why an Executive's Calendar Is Like a Strobe Light

Jessica explains that people misjudge influence because they don't understand how executives actually experience their day. An exec ricochets between finance, hiring, legal, and product reviews, and hasn't thought about your problem since you last met, even if you've prepped for weeks. You have to help them context-switch into your topic rather than assuming they arrive primed.

An exec's calendar jumps from budget to interviews to people problems to legal to product reviews with no gaps
The PM has prepped for weeks; the exec 'hasn't thought about you since' the last conversation
Everything on an exec's plate reads as an emergency, so they can't naturally center your problem
Spend 30 seconds at the top of a meeting reframing why you're there and why it matters

“But I describe an executive's calendar as like a strobe light going off.”
Jessica Fain · 07:30

“But the executive coming into that session hasn't thought about you since. They may not have gone to the bathroom today, right?”
Jessica Fain · 08:00

#influence#executives#meetings#product-management

Explainer1:12:30

What AI Can't Do: Be an Anthropologist, and Solve Distribution

Jessica notes AI is built on a corpus of existing knowledge and isn't a good anthropologist yet, so novel user insight still comes from human empathy and business understanding. With software about to flood the market, the new bottleneck becomes distribution — who gets attention, decided by marketing dollars, brand, and existing customer base. Trust with users and internal teams is the other durable human advantage, and it's a function of influence.

AI is based on existing knowledge and isn't a good anthropologist yet
Novel insight comes from human empathy and business/industry understanding
As software floods the market, distribution becomes the key bottleneck
Attention still flows to marketing dollars, brand reputation, and existing customer base

“You know, AI is not good at being an anthropologist yet, right? It is based on a corpus of existing knowledge.”
Jessica Fain · 1:12:30

#ai#distribution#user-research#product-management

Story· 1

Story38:00

Follow the Subtle Threads Execs Leave You

Jessica says the best people act on the subtle 'breadcrumbs' execs drop — an offhand 'I wonder if…' or 'have you considered…' — rather than waiting for an explicit ask. She contrasts Webflow's Kev, who turned a casual comment from the CPO into a Loom framework within an hour, with a past strategy review where she failed to act on a repeated request and the exec grew visibly frustrated. Ignoring these cues makes leaders lose faith you'll follow up on what matters to them.

Most exec asks are subtle ('I wonder if…', 'have you considered…'), not clear-cut briefs
Kev turned an unprompted CPO comment into a Loom framework within an hour
In a past review, ignoring a four-times-repeated request left the exec frustrated
Not acting on subtle feedback makes leaders lose faith you'll follow up

“And what I find is that people don't take the bait and the best people do.”
Jessica Fain · 38:30

#influence#feedback#executives#responsiveness

Tool· 4

Tool17:00

The Disarming Question: 'What Led You to Believe That?'

When an exec says something you disagree with, Jessica's move is genuine curiosity rather than a yes-man nod or a head-on argument. Asking what led them to a belief co-creates the answer with them and surfaces the pressure or experience behind their certainty. Execs seem certain because they have to make fast decisions on little information, so unpacking the 'why' gets you to a better solution together.

You get paid to have an opinion and be the domain expert, not to be a yes-man
When you hear something you think is wrong, ask what led them to that belief
The question co-creates the answer and surfaces board pressure or a recent meeting driving it
Execs seem certain because they make fast decisions with little information

“That's so interesting. What led you to believe that?”
Jessica Fain · 17:30

#influence#communication#questions#executives

Tool19:30

Train an AI on Your Exec to Pressure-Test Your Pitch

Jessica describes using AI to prepare before a pitch by simulating the executive you're trying to convince. A colleague trained a GPT on publicly available transcripts of past product reviews, and PMs are expected to run their PRDs through it to find pushback and weaknesses. You can also point AI at your own known weak spots, like thin data or shallow UX thinking.

A colleague trained a GPT on publicly available past product-review transcripts
PMs run their PRDs/pitches through it to anticipate pushback before the real review
Ask tools like Slackbot what a leader has been posting about lately
Also point AI at your own known weaknesses (thin data, thin UX) for feedback

“What's Rachel going to push back on? Where are their weaknesses in this ideas?”
Jessica Fain · 20:00

#ai#influence#meeting-prep#tools

Tool42:00

Ask 'How Strongly Do You Feel About This?' to Gauge Urgency

Because execs fire off ideas rapidly without signaling urgency, people over-react and drop everything for a passing comment. Jessica's fix is to explicitly ask how strongly they feel or whether the new idea trumps current priorities. Often they'll say it was just a random thought to backlog, and as a leader she's trying to label her own asks as idea vs. mandate.

Execs move so fast they won't always signal how urgent a request is
Ask 'how strongly do you feel about this?' or whether it trumps current work
If they confirm it's urgent, act; if not, it goes on the backlog
As a leader, label your own comments: 'this is just an idea' vs 'this is a mandate'

“And a great question to ask in that in that scenario is how strongly do you feel about this?”
Jessica Fain · 42:00

“This is just an idea. Um this is a mandate. This is something I want to see.”
Jessica Fain · 43:00

#influence#prioritization#communication#executives

Tool58:30

'Shrinking the Change' to De-Risk a Scary Idea

Citing the book Switch, Jessica recommends 'shrinking the change' — turning a scary, overwhelming initiative into a small experiment or one-week proof of concept so people can get over the hump of committing. Milestones and small chunks that show outcomes build the momentum and trust needed to earn the bigger investment later. Reducing the risk makes it far easier for a leader to say yes.

From the book Switch: shrink an overwhelming change into a small experiment
A one-week proof of concept lowers the barrier to committing
Milestones and visible outcomes build momentum and trust for the bigger ask
Reducing investment and risk makes it easier for leaders to buy in

“If something seems scary and overwhelming, how do you make it so much smaller so that it's an experiment?”
Jessica Fain · 58:30

#influence#change-management#trust#books

Takeaway· 3

Takeaway23:00

Bring Three Options, Not One (and Keep the Rest in the Appendix)

Jessica warns against two opposite mistakes: dumping all your proof upfront (which bores execs) and offering only a single option (which looks like you missed something). Presenting a few options, with a Goldilocks pick in the middle, shows you considered the space. Keep the full set of considered alternatives ready in an appendix in case they dig in.

Don't front-load every proof point; put the homework in the appendix
Offering only one option makes execs feel you missed something
Three options with a Goldilocks middle shows you considered the space
At Slack, a design rule was 'Stuart plus two more' — build his ask plus two alternatives to debate

“give three options and the goldilocks in the middle is the perfect one.”
Jessica Fain · 23:30

“So, we did exactly what he asked for and then two other versions that we felt good about.”
Jessica Fain · 25:30

#influence#product-reviews#decision-making#communication

Takeaway30:00

Execs Want to Succeed Too — Tie Your Pitch to Their Success

A core lever of influence is understanding what success looks like for the exec and connecting your proposal to it. Execs want to be good at their jobs and hit their goals, so map how your idea moves the metric, OKR, or board pressure they're accountable for. If your local team incentives don't align with theirs, you're in misalignment from the start and should have that conversation.

Execs want to be successful and good at their jobs, not just approve or reject
Point out how your proposal improves the metric, OKR, or board pressure they own
Ideally your team-level incentives closely align with the exec's incentives
If they don't align, surface that misalignment early

“The other thing people don't realize is excepts want to be successful, too. They want to be good at their jobs.”
Jessica Fain · 30:00

#influence#incentives#okrs#strategy

Takeaway49:30

Execs Aren't Bound by Your Constraints — So Ask for What You Need

Jessica points out that executives don't feel the same budget, headcount, and timeline limits you do — they can move people, elevate or kill projects, and unlock resources. So instead of accepting 'not possible' with your current team, present the 10x case and name exactly what you'd need to hit it. People routinely miss out by failing to ask for what they need, especially when the exec's ask seems unreasonable.

Execs can reallocate people, add resourcing, and elevate or kill projects
Frame the 10x/accelerated case and state what you need to reach it
If an ask isn't possible with current resources, tell them why not
People constantly fail to ask for what they need to be successful

“people miss out on this all the time of not asking for what they need to be successful, especially when the ask from the executive…”
Jessica Fain · 50:30

#influence#resourcing#executives#ambition

Key ideas

Frameworks in this episode

Anchor the Pitch to the Exec's Incentives

Follow the Breadcrumbs and Calibrate Urgency

Shrink the Change to Build Trust

Stewart Plus Two More

The 60-Second Meeting Reset

Themes for Discussion at the Top of the Doc

Treat the Executive as Your Key User

People & resources mentioned

People · 15

Resources · 40

Insights & moments

⚡Myth Buster· 1

Influence Isn't Politics: Reframing the 'Icky' Feeling

◆Hot Take· 3

Hot Take: Stop Asking Execs 'What's Top of Mind for You?'

The Best Way to Build Trust Is to Kill Things

AI Ushers In a Golden Age of Product Management (Not Product Managers)

✶Explainer· 2

Why an Executive's Calendar Is Like a Strobe Light

What AI Can't Do: Be an Anthropologist, and Solve Distribution

❝Story· 1

Follow the Subtle Threads Execs Leave You

✦Tool· 4

The Disarming Question: 'What Led You to Believe That?'

Train an AI on Your Exec to Pressure-Test Your Pitch

Ask 'How Strongly Do You Feel About This?' to Gauge Urgency

'Shrinking the Change' to De-Risk a Scary Idea

▲Takeaway· 3

Bring Three Options, Not One (and Keep the Rest in the Appendix)

Execs Want to Succeed Too — Tie Your Pitch to Their Success

Execs Aren't Bound by Your Constraints — So Ask for What You Need

Myth Buster· 1

Hot Take· 3

Explainer· 2

Story· 1

Tool· 4

Takeaway· 3