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

22 Mar 2026 31 published claims 2 attributable people
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Speakers in the public record

Jessica FainLenny Rachitsky

Claim mix

belief 17recommendation 4evaluation 3commitment 2preference 2uncertainty 1observation 1prediction 1

Evidence policy

Every row below preserves an exact excerpt. Identified speakers are linked; unresolved voices are labeled and excluded from people counts.

Claim ledger

The useful parts, with receipts.

31 published records

01 / recommendation

They are running around context switching in the most insane ways I've ever seen, and everything that comes across their plate is an emergency. So one of the biggest tactics I think is so important is, just take 30 seconds at the top of a meeting.

“They are running around context switching in the most insane ways I've ever seen, and everything that comes across their plate is an emergency. So one of the biggest tactics I think is so important is, just take 30 seconds at the top of a meeting.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

02 / commitment

If we each think of ourselves as owners and as contributors to the business and as leaders, we will bring those opportunities up as well to both amplify the business or save it from itself.

“If we each think of ourselves as owners and as contributors to the business and as leaders, we will bring those opportunities up as well to both amplify the business or save it from itself.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

03 / belief

The way I think about this right now is just where humans are still necessary and great product thinkers are still necessary is on the front end deciding what to prioritize and build, on the back end, determining if this is good and ready, essentially judgment and taste. And then there's distribution I think is such an underappreciated new bottleneck, because as you said, there's so much shit out there.

“The way I think about this right now is just where humans are still necessary and great product thinkers are still necessary is on the front end deciding what to prioritize and build, on the back end, determining if this is good and ready, essentially judgment and taste. And then there's distribution I think is such an underappreciated new bottleneck, because as you said, there's so much shit out there.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

04 / belief

Tamar, don't be mad if I mess up your title. And what I learned through that process is that people completely misunderstand how executives make decisions, what is going on in the heads, in the calendars, in the incentive structures of executives.

“Tamar, don't be mad if I mess up your title. And what I learned through that process is that people completely misunderstand how executives make decisions, what is going on in the heads, in the calendars, in the incentive structures of executives.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

05 / belief

I think the inverse of this is how do you use that incentive structure to also inform regular roadmap, not just net new product ideas or net new pitches, but you're actually imbuing your entire team and your thought process with that incentive structure.

“I think the inverse of this is how do you use that incentive structure to also inform regular roadmap, not just net new product ideas or net new pitches, but you're actually imbuing your entire team and your thought process with that incentive structure.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

06 / belief

I still don't know because it's a really, really hard job and I have just way more respect than I ever did before that. But I think that if you want to grow into a product leadership role, expanding your viewpoint, expanding the way that you see problems, and thinking about it from a global perspective is a way to show up as that strategic leader that you say you want to be.

“I still don't know because it's a really, really hard job and I have just way more respect than I ever did before that. But I think that if you want to grow into a product leadership role, expanding your viewpoint, expanding the way that you see problems, and thinking about it from a global perspective is a way to show up as that strategic leader that you say you want to be.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

07 / uncertainty

Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now.

“Now more than ever, that is not possible. And so one trick that I learned, especially working with engineers who often have a very, very high desire for certainty, is to say, "I don't know the answer right now.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

08 / belief

If you want to have an empowered EPDI organization or company, that clarity of what you believe, what are the most important problems to invest time and energy into, where we want to invest compute and dollars, that is the mechanism for letting people go and run at as fast a velocity as they're capable of. So if you have that corpus of shared beliefs that you update on a pretty fast clip, because I think that's the mode we're in, that is actually what enables teams to build the right stuff as opposed to just the idea that Claude had.

“If you want to have an empowered EPDI organization or company, that clarity of what you believe, what are the most important problems to invest time and energy into, where we want to invest compute and dollars, that is the mechanism for letting people go and run at as fast a velocity as they're capable of. So if you have that corpus of shared beliefs that you update on a pretty fast clip, because I think that's the mode we're in, that is actually what enables teams to build the right stuff as opposed to just the idea that Claude had.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

09 / belief

Something that we hear a lot on this podcast, is as a product leader, as a leader of any kind, you want to have a point of view, you want to come into a discussion with, "Here's our options, here's what I think is the right solution.

“Something that we hear a lot on this podcast, is as a product leader, as a leader of any kind, you want to have a point of view, you want to come into a discussion with, "Here's our options, here's what I think is the right solution.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

11 / belief

Base this on more corporate context than I could ever have gone through myself and poke holes. And I think that that is just a really powerful way for amplifying our work.

“Base this on more corporate context than I could ever have gone through myself and poke holes. And I think that that is just a really powerful way for amplifying our work.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

12 / belief

I think. I might be getting it wrong, but it's called Overstory, which is a concept of when you have a big tree, like the overstory is the branches that kind of sit on top, that kind of create a shade.

“I think. I might be getting it wrong, but it's called Overstory, which is a concept of when you have a big tree, like the overstory is the branches that kind of sit on top, that kind of create a shade.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

13 / observation

Your job is to help them see how massive an opportunity this is and not just give you what you want, but just like, wow, okay, here's the way to unblock this thing.

“Your job is to help them see how massive an opportunity this is and not just give you what you want, but just like, wow, okay, here's the way to unblock this thing.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

16 / belief

Influence is about increasing the odds that your good ideas survive. And I think what happens is people actually let ego and let their own narrative, their own scope of influence, get in the way of empathy.

“Influence is about increasing the odds that your good ideas survive. And I think what happens is people actually let ego and let their own narrative, their own scope of influence, get in the way of empathy.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

17 / belief

I am not a very online person, which is funny for being on this podcast. So I think the main place I am online is on LinkedIn, and so you could definitely find me there.

“I am not a very online person, which is funny for being on this podcast. So I think the main place I am online is on LinkedIn, and so you could definitely find me there.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

18 / belief

I think as product builders, there's almost not a skill that's more important. Influence and building momentum behind great ideas is the way that great products actually get built.

“I think as product builders, there's almost not a skill that's more important. Influence and building momentum behind great ideas is the way that great products actually get built.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

19 / belief

Distribution is everything. And I think the quintessential example we've seen here is with Gemini and Google's tools and just their total continued dominance in that market because of tools of distribution.

“Distribution is everything. And I think the quintessential example we've seen here is with Gemini and Google's tools and just their total continued dominance in that market because of tools of distribution.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

22 / commitment

If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates, or the marketing team thinks that signups would be 10X because of this, if you have that cross-functional alignment, and this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but that if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf, I think that we now have more tools than ever to, as product folks, build out the V1, prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in to the point that the exec can't say no to the funding.

“If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates, or the marketing team thinks that signups would be 10X because of this, if you have that cross-functional alignment, and this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but that if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf, I think that we now have more tools than ever to, as product folks, build out the V1, prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in to the point that the exec can't say no to the funding.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

23 / recommendation

Then there's your advice of ask people that know them, what is top of mind for them right now? Because they may be like, "This is the big bet we're making right now.

“Then there's your advice of ask people that know them, what is top of mind for them right now? Because they may be like, "This is the big bet we're making right now.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

24 / evaluation

" I think one thing that really trips people up is execs are so good at seeming certain. They say things in an authoritative way with confidence, with surety, because so much of their work is having to make those ultra-fast decisions with little information.

“" I think one thing that really trips people up is execs are so good at seeming certain. They say things in an authoritative way with confidence, with surety, because so much of their work is having to make those ultra-fast decisions with little information.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

26 / evaluation

We talk about this a lot, especially when we think about identity, security, compliance, that agents are a teammate for accelerating work, and the risks that that also provides because of the places where agents fall down.

“We talk about this a lot, especially when we think about identity, security, compliance, that agents are a teammate for accelerating work, and the risks that that also provides because of the places where agents fall down.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

27 / preference

I will tell you, I am not a big fan of the what's top of mind for you question. This is a hot take because I think that what often people do is they think through their top priorities, their top experiences.

“I will tell you, I am not a big fan of the what's top of mind for you question. This is a hot take because I think that what often people do is they think through their top priorities, their top experiences.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

29 / recommendation

Just to make it very clear for people, because it's easy to just like, "Yeah, okay, I'll just expand my horizon," basically, the advice here is just think on behalf of the entire business, not just your feature, not just your little goal.

“Just to make it very clear for people, because it's easy to just like, "Yeah, okay, I'll just expand my horizon," basically, the advice here is just think on behalf of the entire business, not just your feature, not just your little goal.”
Speaker
Lenny Rachitsky
Publisher
Lenny's Podcast

30 / recommendation

You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to the place that they're at because they learned and they developed a skill that you're trying to gain, awesome.

“You need to go work somewhere else. But if you respect them, if you think they have something to offer you, that they got to the place that they're at because they learned and they developed a skill that you're trying to gain, awesome.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast

31 / prediction

I think that we are entering a golden age of product management, not of product managers, but of product management and the core skills that made this function the thing that I love to do.

“I think that we are entering a golden age of product management, not of product managers, but of product management and the core skills that made this function the thing that I love to do.”
Speaker
Jessica Fain
Publisher
Lenny's Podcast
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