YouSaid · the spoken record

Jessica Fain

lines on the record: 96
first: 2026-03-22
most recent: 2026-03-22
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“And then the 30 seconds, I would say we're here to discuss XYZ. Last time we met, we left it off here. The goals of today's meetings are ZYX. Here's how we're going to run this meeting and then stop talking because the moment you go off over 60 seconds, you've lost them. And oh, I think the other really important thing I would add there is to say, was there anything else you were hoping to cover today?”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“And they'll say, Oh, no, no, that's just like a random idea, put it on the backlog. I think that execs are moving so quickly that they won't always give you that context of urgency. And so you have to ask for it. This is something I've been working on getting better at as a leader. This is just an idea. This is a mandate. This is something I want to see. But it's hard. Sometimes it's hard to remember to do that because your brain is spinning with ideas.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, and a great question to ask in that scenario is how strongly do you feel about this? So if you hear something that they say really strongly or how urgent do you think that is? Or, hey, here's what the team is working on now. Do you think that that trumps these priorities? And if they say yes, listen, do the thing that they say trumps it, right? It's not about jumping on every request or taking every piece of feedback. It's about contextualizing it in why they believe that, what they think the urgency is, and then actually responding to that. So more often than not, they'll say, I wonder if we could do this kind of study. And people will go and say, oh my gosh, we have to go run that study right now. We have to deprioritize everything else. But if you say to them, hey, that's a really cool idea. I like that. Do you think that that's more important than these three other studies or three other projects that we're working on now?”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely. I mean, I think 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 have to act like a CPO. You have to come in with that perspective. You have to come in with a solution. You have to follow the thread that they've asked about. You have to do it quickly. One of the missteps here is, you know, people treat these interactions as so high seeks and sometimes they are, but one of the ways that you fail at that interaction is you wait too long to engage on the feedback. If you wait a week for the follow-up items that you discussed in the meeting, that exec has moved on. And you've missed your chance to actually respond to the feedback in a quick manner, you will get so much more excitement, enthusiasm, brain power from them if you keep the ball rolling in a timely manner.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Pulling on, maybe you think that that's not an important thing to do. And then you need more information about why they think it's important. Because if you just let it go and you don't respond to the feedback or respond to the ask, that person loses faith in you that you're going to follow up on the thing that they believe is important.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“To keep everyone really excited about what they're building as well. And he knew that he could slot in and respond to this feedback really, really quickly. A lot of times I see people don't take that invitation from the executive to actually engage on the feet that subtle feedback they're giving. An example from my past where this didn't go as well was We were in a strategy review, you know, sort of a quarterly strategy review. And it was probably the fourth time I had heard Tamar ask, I want to see, I'm interested in seeing the top 10 use cases on X. And the fourth time it happened, she got really frustrated. She said, we've talked about this so many times before. Why don't we have this documented? And I think it's because people are not picking up on the queue that there's really something deep underneath. There's really an important piece of feedback or a question that they're not.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“And I think in that is a disarming of the executive, you know, again, going back to like, how do you get the best out of them? And the best people do. So I'll give you an example just last week, you know, we've been working a lot on as skills get democratized across Webflow, everyone can do design, everyone can ship code, everyone can write a PRD. How are we enabling people to move as fast as their brains and tools will make them? Rachel, our CPO said, you know, hey, Kev, our head of design, we're going to have to think about design reviews at some point. And within an hour, Kev had had a loom put together of, hey, here's a framework of high risk design changes, low risk design changes, blast radius, release processes, and how we might allow anyone in the organization to have designs shipped to production. That was a thread she didn't ask him to do that. He didn't need to follow up in that time frame, but he recognized that the organization's incentives are to keep empowering people, to keep everyone moving fast.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, and I think a big part of this is also metrics and data and what you're actually measuring your own teams on. You know, we talk a lot about leading and lagging indicators or in the nonprofit world, this is called theory of change. There are many steps. You yourself and your individual team may not be able to directly move enterprise revenue or directly move conversion rate, but you believe, and the company has a belief, that painting the inside of the cabinets, having an exceptional customer experience will be the thing that leads to customer attention, customer conversion, user satisfaction. And so how do you make sure that your metrics and the things that you are proposing to actually shift ladder up really, really clearly to those and that your executive agrees to that?”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think that aligning your incentives is, yes, really, really important in a product pitch. If you're thinking about a product pitch, how does it connect to the company goals? Are you trying to improve conversion rates? Are you trying to grow enterprise customers? Are you trying to be perceived in brand? Are you trying to break into some new category? Of course. You have to align on a new pitch. 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. It's a deep understanding how did the OKRs get to be the way they are? How did the positioning statement get to be that way? How do I understand that and deeply embed it into my team's culture so that we're reflecting what our”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Made it a huge deal. We made it really exciting and fun, and we had a big, really fun judging competition that our executives took part of. And we really brought back that part of our culture that we had lost out on a bit. And it spoke to what our executives believed was a differentiation for us and how we were going to show up in the market, show up to our users, grow our user base by making it feel special. And we were able to say, oh, we shipped 65 improvements this week, this sprint. And that felt really, really aligned with what they were trying to accomplish from a company perspective as well.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Usability to a 10x place. And there was a sense that I had heard from our leadership that we weren't quite there and we had lost some of that. And that was so, so important to who we were and how we showed up for our users. And so we implemented something called the customer love sprint. We said, okay, engineering, stop what you're doing as an entire team, we're going to spend two weeks just painting the inside of the cabinets. The only rule was engineers got to pick what they worked on. We supported them from a PM and design and customer support perspective. We gave them tons of ideas, but engineers could pick what they worked on. The only rule was that you had to ship something. You had to ship something that was good for users. And what we did is, you know, you could call this a bug bash. You could say, okay, you got to fix these, you know, these rough edges, these misses in the product.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“And we talked about painting the insides of the cabinets. We really wanted such an amazing experience for our users. That was one of the things that made Slack great in the first place was just it really felt like a product that took that”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“And in building products together, your incentives should be making your users successful, making your business successful because of that. And so what do they actually believe about that? It's not just about, oh, they want a promotion or they don't want to get fired or they want to hit their KR. Those are very, very real human things. But in an ideal world, in product work, it is really based on building incredible products for your users and therefore great outcomes for your business. And so I think a big part of this is actually understanding their strategic insights and what they believe is going to move the business forward most effectively. So after I was chief of staff, I took over Slack's core product team. We worked on channels and emoji and search and messaging. And there was a real feeling from our executive team that we had a bit lost our mojo around product craft.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Top of mind has become this sort of trope, right? It execs right a weekly write up of what's top of mind. And it sort of becomes this generic uninteresting sort of neutralized frame. And so I think the question what's top of mind for you has actually lost some of its firepower. And instead, we have to get at what is the emotion, the sort of drive behind it and what the spicier question that'll get a more interesting answer”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“And sure, is getting pressures, right? What are you seeing as the key inputs to your success? The other thing people don't realize is success want to be successful too. They want to be good at their job. One of the things people really miss out on here is What are the success criteria for an exec? And how do you model your world to amplify that success so that both of you can be more successful?”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“I will tell you I am not a big fan of the what's top of mind for you question. This a ha take because I think that what often people do is they think through their top priorities, their top experiences, you know, if we were trying to do a research study to understand the day-to-day lives of our users, we probably wouldn't say what's top of mind for you. We'd say, tell me how you spent your day. We'd say what's the most urgent priority for you right now that you're really scared about messing up what pressures are you facing? And so I think there's ways for us to ask much more interesting questions of our executives. I recently did this with our CEO. I said, tell me what the board is pushing you on. Because everyone's got a boss, even a CEO who seems so powerful and competent.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Particularly effective means for very busy people and short meetings, and especially in remote work where presentations just don't work very well. Some execs are willing to do prereads, some aren't. And I think you just have to be willing to accept that they are also human and you're trying to give them the best shot at inculcating the information in the way that is meaningful to them.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think that's a really good way of doing it. I think my only gloss on that would be that people are really different, right? Like execs are people too. And so one of the things that I think is really important is understanding what is the literal format, storytelling, pre-work that is going to work for that person. You know, some people hate a PowerPoint and it's just going to crush their soul if you start doing that. Some people only want to see the data and not the user, you know, the qualitative research. And so I do think it is about really understanding their communication style and execs if you're listening to this. It's really fucking helpful if you tell people because you actually know what you like and don't like. And so just tell people, I prefer a doc. I want no upfront explanation. I want 10 minutes of quiet reading time. And then we can come back together. That's a...”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“But at least be ready to show them. Have them in an appendix, have them in a draft Figma file, whatever it is. We used to have this rule after a design review with Stuart. We'd go through the design review and he'd say, no, do it exactly like this. I want the button here and the interaction to be this. And frankly, he always had better ideas than we did. But we would come back and we called it Stuart plus two more. So we did exactly what he asked for and then two other versions that we felt good about. And then it gave us a forum for conversation to debate the merits of each type of approach.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Review is we said, Hey, we really want to sort this out. We want to get moving. We want to show that we can really get building on this product. And alignment is the next stepping stone for that. Can you meet in two days? And we turned around a new doc in two days that actually showed all of the options we had considered but hadn't brought to that first review. And once we elucidated all the things we considered and why we thought they would or wouldn't serve the outcomes we were driving and the technical complexity behind them, she was like, oh, yeah, okay, I see why the solution that you're proposing makes the most sense for what we're trying to accomplish. But in the first version, in the first meeting, we hadn't kind of shown that and we hadn't workshopped it through her. And so sometimes, you know, really tactically, you want to have that available to you. It's not necessary to put all 15 options you can.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Your work that helps elucidate why your solution is best. So, one of the mistakes I see people giving is doing is giving only one option I think that people, if you say, I mean, this is also like classic pricing and packaging strategy, give three options and the Goldilocks in the middle is the perfect one, right? But I think that what that actually allows you to do is say, hey, we considered, we are not dumb. We did not miss something. You think we missed something, but no, no, no. We actually considered this. So we had a recent product review with my manager, Rachel Wollen. She was a recent guest on how IAI. brought a doc, a sort of reasonable approach to what we thought was the sort of problem and strategic space we were going after. It didn't go well. It really didn't match our expectations. And the feedback she gave us, which was really, really the right feedback, was, I don't understand how you're thinking about the permutations of possible here because we had only given one option set. And so what we did following that.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, so my advice on this may be a little paradoxical because I think people make mistakes in both directions on the polls here. On the one hand, I think there's an error people make of trying to show too much work, trying to too much upfront proof point. We talk to 16 participants from these 15 GEOs and this is the statistically significant and the exec is like, I'm so bored I'm going to die. I remember I did this in a review once and literally the person I was most trying to convince glazed over, got on their phone and I totally blew the meeting because I was trying to prove that I had done my homework. Put it in the appendix, right? They don't need to know every single detail the baseline expectation is that you did your job and that this that this is built on a solid foundation of your domain expertise. On the flip side, I think there's some balance of showing”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Stuart, because we realized we were coming to him with like done designs, and he was like, What the is this? This is completely different than how I had this in my mind. So Ally Rail, early Slack employee implemented something called Hey Stuart, what do you think? And we would just sit with him for half an hour and say, what do you think on this topic? What's your belief system? What's your past experience? And we started with a user interview, right? We started with we actually want to download your expertise here. I think that when you engage execs in that way, it's really, really valuable. Like one of the things I see people do poorly is they don't ask for the time. This is sort of a counterpoint to what we were talking about before with how busy their calendars are, but they're afraid to ask for more time to get that insight. But sometimes if you don't, you miss the point.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“From past product reviews that are all publicly available, and we expect that our PMs are running their PRDs or their pitches through that to say, what's Rachel going to push back on? Where are their weaknesses in this ideas? You can also train things on where are your own weaknesses. I know I've gotten feedback in the past that my data is a little thin or that this kind of UX thinking is thin. Give me feedback on that. Claude's amazing for this. And so I think that the first step is actually just saying what's important to them, what do they want to hear and anchor on that? I think the second piece is going in to learn not to convince. And the earlier on you do that, the better. So we have something at Webflow called Office Hours as early as you can. You are having these conversations to align on strategic direction. Maybe even before you have a one-pager. You know, we implemented something at Slack with.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“The earlier that you can understand the belief system and the things that are important to them, the better off you're going to be. So very, very early on in this process, what is top of mind for them? I can count on one hand when I was chief of staff how many people asked me for advice before going into a product review with our CPO or other executive team to say, what do you think is most important to them right now? Use the people around them, their EA, their chief of staff, the people who have successfully pitched ideas in the past and say, what worked? What do you think they're worried about? What are the risks? And in an age of the tools of AI that we have, this is so much easier than it's ever been, right? You can ask Slackbot, what is Rachel been posting about lately? What do you think is most important to her? A colleague of mine appear on our product leadership team, trained a GPT on a bunch of transcripts.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. But if this is someone who is also a learner, who also has a growth mindset, then if you are able to help them unpack why they believe something and then respond with your own domain expertise, you are able to get to a better solution together.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“That kind of question is actually curious about this person said something that I think is dumb, but there must be something behind it. And so if I actually care what's behind it and what you end up doing in that question is co-creating with the person who offered the opinion in the first place. You're able to say to them, I'm interested in what led you to that belief, your experience. Did you have a meeting last week? Are you getting pressure from the board right now in a certain way? What is leading you to that belief? I think one thing that really trips people up is”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Strong enterprise background. So he could bring that to the forefront. I think that has to be married again with that curiosity and empathy. If you hear something that you don't agree with, this is something that on a guy my team does super, super well right now, you know, he'll hear something that flies in the face of what he's the data he's seeing, the insights he's gotten, his experience in his domain expertise. And he'll say that's so interesting. What led you to believe that?”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“One assumption I have of how folks may misunderstand this skill is that they have to be a yes man. They have to take everything that the leader said and do exactly that. That is absolutely wrong. You get paid to have an opinion. You get paid to be a domain expert. And in a lot of ways, your executive is looking for you to be the deepest person in the room, especially if they're good at their job, right? They're looking for you to be the expert. And so bringing your expertise to bear is absolutely crucial. You know, Elon Frank, who was my boss at Slack as well, is now CPO of Checker. He always had a customer anecdote in his back pocket. Like I can hear him in my head saying, I was just on site last week with so-and-so. And they said, blah, blah, blah, right? He always brought his expertise to bear. And many of the executives at Slack were not from.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Allowed him to do was reflect back to Stuart ideas and principles that he had, but also grow his own product sense, intuition. And as an organization, it then allowed us to scale those principles. And I think was a really, really important. They weren't trying to politic. They were trying to build great products. And that's the approach we have to take”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“I've learned so much from Noah. We sat down to write product principles for Slack and Ethan Eisman, our head of design, was leading that initiative. But really this was a lot about codifying the early ideas that made Slack great, especially from product principles and sort of craft perspective. And we started talking about this. And Noah had been at Slack early on. And he pulls out like a small notebook that he kept in his bag and he said, you know, I actually have a section of this notebook that I've been keeping things I learned from Stuart over the years. Now, he hadn't been keeping that notebook because he said to himself, oh, one day we're going to write product principles and I'm going to want these quotes on hand or I'm going to show off that I have this. No, it was for genuine learning and growth of his own ideas and place as a product leader that he was taking those and what it is.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think that when people frame this as politics, they're completely missing the point. Politics is manipulating outcomes in people for your own gain. 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, right? So this isn't politicking. This is learning. If we treat our stakeholder conversations as discovery interviews, as a way to strengthen our ideas, then we end up in a much, much better place. And if we do that in a genuine and low we go way, I'll give an example here. Noah Weiss, who seceded Tamari Oshua as CPO of Slack and former podcast guest.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Fine. If you don't respect that person, if you don't believe they know something you don't, you need to quit. 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. Take the feedback, take the insight, ask questions, and don't just treat it like a rubber stamp because that's a failure state and it's a failure state that they don't like.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Our key user here, then we can have a much, much more productive conversation. You know, I think one of the most disastrous things you can do is go into a meeting just looking for approval for your plan. Instead, if what you go in with is, how can I learn? How can I strengthen this plan? How can I use the domain expertise, the context, the experience that this person brings to the table and imbue that into my product work, both the executive will like you better because they will feel like you have actually built product alongside them, but you will also end up with a better product. You know, I often hear people say to me, oh, they just don't get it, right? They don't see what I see. They're not in my meetings. They don't know how hard this is.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Also, former podcast guest, former CPO at Calendly in Glassdoor, and now at Microsoft. And Annie's just the best. She always said to me, it's not my fault, but it is my problem. And I think that that's the vantage point that a product leader has to have, especially if they're trying to put themselves in the shoes of an executive. As product manager is 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 or to a stakeholder, we forget those skills and those talents and we begin to think about our ideas getting that approval, getting to the next meeting, whatever it might be, the incentive that we are driving. We don't think about the curiosity and empathy for what they're thinking about, for what their incentives are, for how their day has been. And if we can take some of those skills of building great products and think about our executive as”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. I think that, you know, one of the ways that I phrased this is how do you get the best out of your exec? How do you help them be their best selves? We often think about how we show up in a meeting or the doc that we rode or the prototype that we've got ready, but we don't think about how they can be at their best. How do we give them the right kind of information in the way that they communicate? You know, we as product leaders have to be communication chameleons. We have to be speaking their language, like love languages, right? But appropriate for work. And you have to think about do they really turn a spark with a design, with a customer story, with a dashboard, with an experiment? How do you understand how their best brain, how their best expertise gets turned on to give you the best of themselves? But part of that is literally just setting up a meeting effectively so that they”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“They may not have gone to the bathroom today, right? And you have to understand that they have not had the time, the energy, the wherewithal to center your problems and you have to help them get into that mindset. So this is as simple as execs are people too, right? 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. Why are we here? What happened the last time we talked? Why is this important to you? Why is this meaningful? And really remember that they are not thinking just about you. They are optimizing for a global maximum and not for the local that you're optimizing for.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh my gosh, I think the biggest example of this is people don't understand executive calendars, right? A lot of times on Google Calendar, it's blocked. You can't see what they're working on. But I describe an executive's calendar as like a strobe going off. You know, you wake up at 8 a.m. You've already got a huge list of urgent things going on. You go from a meeting with finance on a budget to an interview for another executive to a people problem to a legal problem to a problem. Thinks I've been prepping for this meeting for two weeks, three weeks, maybe six weeks since we last spoke. But the executive coming into that session hasn't thought about you since”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“Who's been on the podcast, right? And is now CPO and head of AI at Atlassian. Tamar, don't be mad if I messed 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. And instead of really understanding where that exec or stakeholder is coming from, they center themselves. They center their own desires, their own motivations, their own slice of the world, and they end up just not being as successful both in their career, but also in the types of products that they're building.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“April Underwood, who had just been named CPO of Slack. She had just come back from maternity leave. We had a two-day overlap. And I sort of got up my courage and I said to her April, I've admired you for a long time. I love the way you work. I really love the way you think. And I really want to understand it better. If you'd ever consider having a chief of staff, I'd love for you to consider me. And when I came back from that maternity leave, I came into a stint as April's chief of staff and was later chief of staff to Mario Hoshua, who seceded April.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think why I wanted to talk to you about this is, you know, when I was an ICPM, I was putting forth ideas, I was trying to reflect what I was hearing from my customers. I was trying to get sort of buy-in and excitement about the work that I thought was really going to move us forward. And at the time that I'm thinking about, I was a PM at Slack. And some of my ideas got people really excited, you know, got me funding and backing and just really a sense that we could accomplish something great. And some of my ideas and the things that I really, really believed in died on the vine. They went nowhere. And I was so confused and frustrated, honestly, because I felt like, hey, I really get this user base. I really understand what's going to move the ball forward. And I don't understand how these decisions are actually being made behind the scenes. And I was eight months pregnant, eight and a half months pregnant.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And if you don't have that influence, if you don't have the buy-in and the backing of your key stakeholders, of your executives, you can't build great products.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's ways for us to ask much more interesting questions of our executives. Tell me what the board is pushing you on. Accepts want to be successful too. They want to be good at their jobs.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 a.m., 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.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source
“As product manager, as 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.”
2026-03-22 · Lenny's Podcast · The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack) · IDENTIFIED FROM THE TRANSCRIPT · source