YouSaid · the spoken record

Jessica Fain

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96
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2026-03-22
most recent
2026-03-22
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1
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  1. “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. In terms of being useful to me, I would love to hear what resonated for you, what's worked for you in the past, how you're seeing these things show up in your work, and how I can get better at, you know, uplifting the tech community. And as we go through this period of tremendous change, how I can show up as a leader and as a source of community for this group of folks.”

    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

  2. “Everyone should go. It's such a fun spot right on UC Berkeley's campus and they've got great music and we're really lucky to live close by.”

    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

  3. “That's such a good question. So these are all my husband's posters. He is a musician. He loves guitar. So he picked them all. But I think that I have to say my favorite one is probably Jimi Hendrix plays the Greek. So we live in Berkeley and it's just slightly off camera, but it's just a great memory of sort of an incredible musician and the iconic place that we're lucky enough to live in and sort of the great access to culture that we have here, but also just how important music is to our lives, how much joy breaks.”

    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

  4. “Right. I've also recently heard if you want a village, be a villager. And so this idea of just building community, reaching out, being there for other people, and really taking that first step, even if it's scary or overwhelming, can really make a difference.”

    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

  5. “I asked my husband about this one. I was like, What's my life motto? And he had such a nice answer that I thought I'd go with it. We have this saying with our kids, first the guess. So if you have guests over, which we love to host people in our house, our role with our three kids is guests always go first. And I think that it's really something that we think about in terms of being of service to others, being respectful to others, being welcoming, being kind. And I think that that has dictated a lot of who I am as a person and how we're trying to be as a family. And it certainly makes the world a little bit better.”

    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

  6. “Air purifiers and whatever. You can set like maintenance for your dishwasher, for your air filters, for your washer dryer, which has been super cool to see. They also, you get handyman credits every month. So all the things that you put off doing, they can come in and do it themselves. And it's just wonderful.”

    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

  7. “But I think more in the tech vein of products I've loved, I've been a loyal user of CASA, which I believe you tweeted about as well as Akasa user. CASA comes in and they have this idea of what if everyone had a household assistant. And so they come in, they take stock of every paint color, every appliance, every light bulb. anytime something breaks or you need something repaired, you can just say, I need new light bulbs for this room and they'll immediately send you them from Amazon. I need a new dishwasher. Ours broke and they'll send you three options that fit your space and are good quality. They also pick up your packages every Friday and your donations. So great. And they're just the nicest people. So I'm really excited to see them see them thrive.”

    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

  8. “It's a separate thing. It's sort of like a basket that you put the towel in, you could put it in for half an hour, an hour, set it on a timer. It's so cool.”

    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

  9. “Okay, I bought my husband a towel warmer. It was like $35 on Amazon, and it has led to so much joy in our household just getting out of the shower to a warm towel is so great. It's a really fun addition to the family. So highly recommend that it's just a cheap and easy way to brighten your day a little bit.”

    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

  10. “You know, again, this is another window. I have been obsessively watching the pit, which is probably a lame answer. I wonder if anyone else has given you that so far. But I just really, it's given me such a vantage point and a view into the incredibly difficult work that emergency healthcare workers do and the stresses and the system and the brokenness that they operate under, but also the extreme care and love that they bring to their work. And it's just given me so much admiration.”

    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

  11. “Of burning is a book that tells a story of Indian indentured servants that were brought to Uganda to build the British Railroad there. And just parts of history that I was so much less familiar with and really treasure that sort of window into a different world.”

    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

  12. “There's a genre of book, I've really fallen in love with. I mentioned Pachenko before I love historical fiction because it really gives me access into worlds that I don't know. You know, I can't remember who talks about windows and mirrors. Books are windows or mirrors for us. And historical fiction, especially about places where I'm less familiar with that history is really a window into someone else's experience. And there's a particular type of historical fiction that I've just loved, which is multi-generational historical fiction. Pachinko does this with a family in Korea over generations and moving to Japan. There's a book called Homegoing, which is about the west coast of Africa and Impact of the Slave Trade and the ongoing life in Africa from two split parts of the family.”

    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

  13. “Around them, to build trust, to build influence in the way that feels true to them. You know, I think when I was younger in my career and I was starting out as a PM, I got a lot of feedback of, oh, Jess, how do you, you know, show up more like a man would, show up more aggressively, show up more decisively. And I think there were some good nuggets in there, but I think it took me a while to feel like, hey, who I am and how I show up is actually my superpower that I can double down on. And I don't need to be like someone else. What I need to do is think about what I want to accomplish and how I want to grow and do that in a way that is true to me.”

    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

  14. “One thing I think that I'll say A people person. I love in person collaboration and I love talking ideas through and whiteboard sessions. I'm a two-way if there are any other Enneagram fans out there. It's a mix of the people person that sort of bringing to the communal thinker with the achiever. That is my personality type. I think that sometimes I can give this kind of advice and people say, oh, well, Jessica, you're good with people or like you kind of understand these things. I think that something that has taken me a while in my career is how to be authentic to myself in influence, in relationships, in trust building. And I don't think that it's one personality type or another. I think that you could be shy and introverted or super data oriented and technical. I think all types of personalities can in their own authentic way communicate with the people.”

    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

  15. “Is an agent is to help our brains be most effective, is to clear out distraction, to point out the most important things, to, and I think this is where people really need to make some tough decisions, how much can we really focus on and how do we allow for that focus in the ways that are hopefully good for humanity.”

    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

  16. “I think that one thing I'm really curious about, you know, you were talking about human brain chemistry is just how we can protect our brains from overwhelm. The speed of ideas change building is we are disolved for this pace of life. We were evolved. I love this book, Pachinko, that tells the history of a Korean family over several generations. And in one of the generations, sort of in the 1600s, 1700s, there are two wives that every day cook breakfast, then go to the market, buy rice, buy fish, buy vegetables, go home, cook the rice, cook the fish, serve dinner, clean up dinner. That's the day. And for the vast majority of human history, that was kind of our day. And the mental load that we are asking of our brains right now is staggering. And so I think one of the ways that we actually have to use AI.”

    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

  17. “Absolutely. Wow, that's really the singularity, isn't it? You should just feed this podcast to a bunch of agents and see if they can do this better than me, see what their advice is. No, but I really think at this point we are in a place where it is a back and forth and where we should be using agents, NAI as a really smart colleague that never gets irritated by our questions. Poke holes in my ideas tell me what you would do differently. Help me plan this out. Base this on more corporate context than I could ever have gone through myself and poke holes. And I think that that is just like a really powerful way for amplifying our work.”

    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

  18. “Product market fit. What do I look for in terms of what success looks like? How do I set metrics? And if we can do that upfront work to actually like analyze ourselves and where we've seen success, where we've seen downfalls, and then continue to train our agent models with that data, that history, that context, they will be better off. But I also think the flip side of this is guardrails. Where do you need to be involved? Where do you need to catch hallucinations or missteps? Where do you uniquely have taste, judgment, frame of reference, something intangible where you need to say, don't do this without me?”

    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

  19. “Love that question. You know, 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. I think agents are absolutely something we have to think about with relation to influence because we are basically all directors of work now, right? If we have an army of agents or this hundred new colleagues that joined our team, how would we onboard new junior team members who don't already understand our product philosophy, what's important to us, and how do we codify that for ourselves? How do we take the time to say, what's important to me as a product leader that I want to inculcate into anything that's developed for my team? What do I believe about”

    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

  20. “Totally strategy clarity is so so important. I am not in the Twitter verse. I find it exhausting partially because I think takes like PRDs are dead or software is dead is like really dumb. I find it a little insufferable if I'm being spicy because I still think what matters is understanding users, understanding business and economic dynamics, understanding strategy and what we're trying to accomplish and then really thinking through what is the right way to do that 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

  21. “Velocity is they're capable of right so if you have that corpus of shared beliefs that you update on a pretty fast clip because I think that's 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.”

    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

  22. “Yeah, I do think that as ideas proliferate and as there just become so many ideas and so much feedback, you know, we're going through a strategy doc rewrite. I think we have like 40 versions now because it's so easy to rev on a 15 page doc. Actually, when these decisions are happening faster, building is happening faster. The flip side of that is mistakes compound faster as well. And strategy clarity becomes so much more important to anchor people on. 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 as 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

  23. “Are still working with millions of users and alongside distribution is trust. And that is a function of influence and empathy.”

    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

  24. “Oh, I want you to do a whole episode on distribution because I feel this so much, right? If everyone thinks they can build the next Salesforce on their own, by the way, I don't believe that, then you're going to have just a flood of available tools. And who gets the attention? It is still going to be who has the marketing dollars, who has the brand reputation, who is the existing customer base, 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. And I think it's really fun to see. I think the other piece I would say is that's underrated there is trust building. Trust with your users, but also with your internal teams. You know, we're seeing even model companies hire at a huge rate right now. So you are still working with colleagues.”

    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

  25. “Yeah. And what can you notice that AI can't? You know, AI is not good at being an anthropologist yet, right? It is based on a corpus of existing knowledge. And I think the best product thinkers, again, across functions that I've worked with really are able to get to novel insights through that user empathy, through that understanding, and through deep understanding of the business dynamics, changing industry, and bringing those together to prioritize ideas that actually really, really matter. You know, we're going to have so much software we won't even know what to do with it, but what software actually works, what software actually matters, what software gets marketed or sold or, you know, we're going to have to think about not just that the software exists, but that it can get to its final state. And that is going to require people's buy-in.”

    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

  26. “That signal on product market fit, on user benefit, and then build momentum from that point in a much faster cycle. And so it's actually like an incredibly exciting place, but the active influence, the active stakeholder management, the act of learning is the 10X skill.”

    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

  27. “Be so incredibly influenced by those court skills of bringing people along for the ride. So I think that product managers for a long time have made their careers on being the most type A, the Gantt chart master, the best note taker in the business. If AI is better than you at analyzing data or taking meeting notes or running experiments, what's your job now? So the leverage actually shifts from doing that work and being the synthesizer to deciding what work actually survives and encouraging other people to buy into that process. And I actually think it's just so incredibly exciting because PMs and other functions, engineers, designers are so empowered to bring that first version to bear to get that momentum to get.”

    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

  28. “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 more than ever, what we have to do is have really interesting ideas that are grounded in user empathy, curiosity, testing, iteration, but we will still be working in organizations where getting buy-in to those ideas and influencing people to fund not just the V1, but the much more expensive V2, 3, 4, and ongoing support become 10x more important. And as execution basically plummets in complexity and everyone can be a builder, PMs can and product thinkers, which I think Is far beyond the product management function 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

  29. “Right, exactly. Right. Think like a CPO. Put yourself in their shoes. I mean, you had Stuart on a few weeks ago and he talked about how the CEO is kind of the only one who can really kill things across things that already exist or really make some of those super, super tough decisions. I think that is oftentimes our culture, but is a mistake. 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.”

    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

  30. “So, you know, so many times I see docs that are like, okay, our KR is to ship this thing. And I'm like, why does that matter? Like, does anyone care? You have to tell a story. And even if that's true, that shipping is the case. Do you need to change course? Do you need to say, hey, actually, I don't think this is the highest leverage thing right now. We could actually do X to be much more effective for our broader goals.”

    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

  31. “Oh, yeah, I mean, he's so charismatic and able to really put himself in other people's shoes. I mean, I think that it is just a way to, you know, we just redid our PM career ladder for this year. And I led that effort. And one of the things that we noted as a trait of becoming more senior is your product citizenship and how much you are embedding back in the organization and giving back best practices, mentoring others, broadening people's horizons on tooling, technology, storytelling, and of course strategy. And I think that this is such an important part of people's growth that they often undersell, but you can do it at every level in your own area. And it's about connecting the dots back up to what is important to the company.”

    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

  32. “I had told April when I originally pitched her on being our chief of staff that I wanted to take the job because I wanted to know if I wanted to be CPO when I grew up. And it's true. 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.”

    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

  33. “Yeah, and I think the other piece of this is for anyone thinking about how they grow their career, how did that person get into the role that they are in? They broadened their context. They saw, you know, sort of had great peripheral vision. And that is a way to show up in a room that is much more senior than you are is keep your domain expertise, keep the things that you know best, but broaden your perspective, broaden your vantage point to think about it in the context of the whole ecosystem, the whole organization, the whole industry, which you often don't get a chance to stand. And what happens at that point is you get seen as a strategic thinker. You get seen as somebody who really cares about the company's success and not just your own. And so it is actually a really, really important tool for growth, especially, you know.”

    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

  34. “They don't show a curiosity for the expertise that that person has brought to bear. And frankly, I think often they don't really care, which is the chief mistake. They should really. Actually, take it into account to strengthen their own thinking.”

    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

  35. “Something people miss is the extremely broad context that execs bring to bear from not only their experiences, but the things that they are hearing in their day-to-day life. They understand what other product teams are working on better than you. They understand the conversation at the e-staff level. They've been to executive roundtables and they are hearing. And one of your jobs is to extract that insight and information and apply it to your ideas. And they want to feel like you care, like you respect that, like you can apply it to your own thinking. And so this keeps going back to that curiosity and empathy. What do they know that you don't that you can actually apply to strengthen your thinking or inform the direction that you want to take your team? And I think people just often don't ask those things of their executive.”

    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

  36. “Right, it's not working. And here's how I'm going to know that's not working. And here's when I'm going to come back to you with a decision, right? So sometimes we don't know that. A lot of times we don't know the outcome, especially with AI native products. And if we can say we're going to test this, here's how we're going to know it's working. We'll come back to you on X date. I think one thing that really spirals people out of control is a desire for certainty. As human beings, many of us have a huge desire for certainty 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. I don't know if this is going to be successful. I'm going to check in with you on X date. That's when we're going to come back and have another conversation. And so at least there's certainty about the next check-in point. And that can be a really powerful.”

    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

  37. “Yeah, I think that's absolutely right. And I think what is the type of risk that they are most afraid of, too, right? Is it wasting time? Is it time to market? Is it that they don't actually think this is going to work with customers? So if you can start to, and you can and should ask this, what are the outcomes you're most afraid of, right? What would a failure state be for you in this experiment? There's a concept of red teaming, which is originally a military tactic and now being applied to businesses. How do you take an outsider's perspective to your idea and not just be so”

    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

  38. “To the way that we develop all products, especially if you're doing something that lasts longer than a month. What are your milestones? What are the chunks at which you're showing outcomes and fit? And this is easier than ever to do with the tools that we have at our disposal. How are we showing that we are taking a much more iterative approach so that you can build that momentum, build that buy-in, and get that trust to do the bigger thing?”

    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

  39. “Amazing things quickly, feeding that back to the leader to say, hey, we worked with you on this, we shipped it, it went well. Here's the result. That builds you momentum to be able to go back with the more novel approach or the scarier one. I think the other thing I would say is one of my favorite, well, actually one of the only business books I've ever liked is called Switch. It's about change management. And they talk a lot about shrinking the change, which is this brilliant idea. If something seems scary and overwhelming, how do you make it so much smaller so that it's an experiment? It's a one week proof of concept. It's something that feels really small that can get people over the hump of, well, I'm not going to invest in six months for this project if I don't know if it's going to work. So shrinking the change is a huge way to build momentum and trust. And I think this applies.”

    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

  40. “Think in terms of building trust, it's really important to ground yourself in what they believe. If you are pitching an idea that is wildly different than something they believe, don't bother. You probably have nine other good ideas that are more aligned with the beliefs that they already hold. Follow those instead. So there's something about just engaging from a baseline assumption. If they feel strongly about something, okay, maybe you can come back to them once or twice and say, are you sure you feel strongly about that? I really see this data. And if they say, yeah, I feel really strongly, you probably have to drop it. But in terms of building that long-term trust, I think the biggest things that do that are really hearing them out and actioning on the feedback that you've gotten in the past. Having results, you know, it cannot be overstated that impact in the organization, building great products, shipping.”

    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

  41. “Yes, and I think there are also really different phases of a relationship. There's a phase when you're new, you may not have so much FaceTime with that person. You don't really know them that well. But I think that this is a place where time spent together really just accelerates your trust with them, your ability to speak freely, to ask difficult questions, to get real feedback. And so especially if you're in a position where you can ask for that time, more casual time, less fraught that you're not always pitching an idea, but you can have real conversations. That is also the groundwork for the pitch down the line. I think people devalue that time up front spent together because it pays dividends for the later pitch.”

    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

  42. “I'm thinking about a tool April Underwood taught me. She said she used to go into product strategy meetings with Stewart and was really trying to extract some of his ideas, but she was always holding the whiteboard marker. And so there was this back and forth between them in the conversation of I'm trying to imbue, I'm trying to understand deeply what you're seeing in the market, what you're feeling in the business, what your instincts are. But I'm also going to package that in a way that is translatable, is actionable, is in a framework that you might not have had in your head. And so that is like a great tool for marrying that leader's instincts with your ability to sort of not synthesize their approach, but really take that approach and accelerate it for marrying what you. You know about the world and what they know about the world.”

    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

  43. “You know, it really depends on what kind of organization you're working in. You know, if you're working in a smaller organization, if that big idea is something that you can build on your own or you can build within versus if you need a large scale investment.”

    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

  44. “Yeah, absolutely. This is going to be our new big bet. And this comes back to aligning with what the company is trying to accomplish and also the urgency. So some things, if you added a dozen more people or perfect alignment with Go to Market, you could get them to market faster. Is that the most important thing for the company goals? Is right now the answer is accelerating this in this way actually going to do more? Or is it something else that's actually more aligned? And so I think it's still being so rooted in the company goals and what the exec is trying to accomplish and what your users really need to be successful so that you can say in order to accelerate our goals, here's what we can do.”

    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

  45. “About that, I need eight more people. I need you twice a week for an hour. I need much closer alignment with our marketing team, and I'm not sure how to get that. You have to think about what are the constraints that hold you back that they can actually help you a lot with. And 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 seems unreasonable.”

    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

  46. “They don't have the same boundaries of budget and headcount and timeline that you feel. They can move people around in the organization. They can ask for more resourcing. They can get creative. They can elevate projects, kill projects. And so you have to come to them with that mindset of, hey, with today's resourcing, with this many engineers, or this kind of tooling or this kind of investment, here's what I can get, but I'm thinking of the 10x case. I'm thinking of the accelerated case. And if that's what you want, and if that's aligned with your incentives, here's what I need to be successful. And so I think that people think, okay, well, I've got my pizza team and I've got my four engineers and what you're asking is not possible. Well, if it's not possible, tell them why not. Come back and say, you know, the thing that you're asking for, I'm super stoked.”

    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

  47. “Yeah, we should have like a stamp influenced at the end. So I think one of the things that people misunderstand is the constraints that they are bound by versus their leadership. You know, execs are 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

  48. “We'll make everything easier. It is also the job, right? You also have to. But I think the thing I want people to take away is that it's really the way to build well. You know, when people are motivated, when they feel purpose, when they feel like this is really something that I believe in, they work harder, they support you more. They talk about you in rooms that you're not in. And so it's just actually the way you deliver great results.”

    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

  49. “I mean, it's literally your job, right? They, I think the way that product management has worked for a long time is you basically get funding for your ideas in the form of engineering, design, you know, cross-functional resourcing, right? That is you should consider that VC money that's been invested in you and your CFO, your CPO, your CEO is expecting a return. And so what is the way that you are showing that you are building great products that honors that investment in you? Sure, you can go into a startup and be the sole decision maker, and that is a very, very valid way to work. But if you work with other people, having them excited, interested, passionate, bought in to what you're doing.”

    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

  50. “Try to actually do that. I think the other thing here is this often depends on what kind of meeting, what you're actually doing. You know, in our culture, we do a lot of sort of silent read of docs or watching a loom in the meeting and then coming back for conversation. I think one of the things that I've seen be really effective in coming back for that conversation is oftentimes a leader will smatter your doc with a hundred comments and you're like, oh my gosh, what is actually important here? So what I often do is I have a section at the top to say themes for discussion. I bubble up some of the biggest and most controversial pieces that can only be discussed live. And anything they've said that they're just curious about, what's the timeframe for this?”

    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