The art of influence: The single most important skill left that AI can’t replace | Jessica Fain
In a Nutshell
Jessica Fain teaches product managers to master influence by empathizing with executives' chaotic "strobe light" calendars, aligning pitches to their goals/OKRs (e.g., "What is the board pushing you on?"), and entering meetings to learn rather than seek approval—using tactics like starting with 30-second context, curious questions ("That's interesting—what led you to believe that?"), Minto Pyramid structure (recommendation first), and presenting 3 options with the preferred "Goldilocks" in the middle. Build trust by killing bad ideas, acting like a CPO with domain expertise, red-teaming proposals, and shrinking changes into low-risk experiments; leverage chief of staffs/EAs for intel and AI tools to simulate exec feedback. In the AI era, influence becomes irreplaceable as execution automates—prioritize strategy clarity, user empathy for novel insights, buy-in for prioritization/distribution, and onboarding AI agents with company context/guardrails.
These notes were generated by AI and may contain inaccuracies.
As product managers, 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. > It's your fault if the leaders didn't buy into your ideas. 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 8:00 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. > What are their goals? What are they trying to do? How are they measured? Connect the thing you're pitching them with that success. There's ways for us to ask much more interesting questions of our executives. Tell me what the board is pushing you on. Execs want to be successful, too. They want to be good at their jobs. Sometimes you have the best idea and they just don't bite. One 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.
Today my guest is Jessica Fain who's been a product leader at Box and Slack and Brightitewheel and now at Webflow and she has gotten very very uniquely good at the art and science of influence and in particular influencing executives. Influence might be the single highest leveraged skill for product leaders outside of AI. We actually get into how AI is changing the skill of influence. I've never heard a podcast conversation get deep into the art and science of influence, how to actually change people's minds and the mistakes that people make when they're trying to influence leaders. We get very tactical and very specific. There's a bunch of stuff in this conversation that I've never heard before or thought about.
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 buyin and the backing of your key stakeholders, of your executives, you can't build great products.
Something that I personally went through is just like I was in a period of like I don't need to work on this skill. I'm just like, I'm just going to do amazing work. It's going to show itself. Everyone's going to recognize it. And you just everyone run into this wall of like, oh man, all these other people are getting promoted.
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 buyin 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, 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 uh I was uh eight months pregnant, eight and a half months pregnant. April Underwood, who had just been named CPO of Slack, um 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 I really love the way you think. Um, 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 Tamar Yaron Joshua, who succeeded April, who's been on the podcast, right? And is now a CPO and head of AI at Atlassian. 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.
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 light 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 product review. And the product manager coming to that product review or the leader who's trying to make a pitch 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. 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.
Tactics to Help Executives Engage
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 wrote 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? We as product leaders have to be communication chameleons. We have to be speaking their language like love languages, right? But appropriate for work. Um, and you have to think about do they really uh turn a spark with a design, with a customer story, with a dashboard, with an experiment, and 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 the meeting effectively so that they can have the context, the wherewithal, the sort of breath at the beginning of the meeting to to dive into it.
It's your fault if the leaders didn't buy into your idea. Like it's not you can't just be like ah they never they just don't see it. It's not my fault. I they they agreed to do something else. I always tell them like that's just you're not able to influence them and convince them that you're right. And Annie Pearl who was my first PM manager back at Box. Also former podcast guest, a former CPO at Calendly and Glassdoor and now at Microsoft. 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 in the shoes of an executive. As product managers, 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 our key user here, then we can have a much much more productive conversation.
Avoid Seeking Approval; Seek to Learn and Strengthen
One of the most disastrous things you can do is going 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. 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." 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.
Some people might be turned off by this topic in terms of it may feel icky of just like uh I don't want to try to be this like manipulative person and you know deal with politics and influence like I just want to do awesome work. Why do I have to do this? 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 in a genuine and low ego way.
Example: Noah Weiss's Notebook of Learnings from Stewart
Noah Weiss who succeeded Tamar Yaron Joshua, CPO of Slack and also former podcast. We sat down uh to write product principles for Slack and uh Ethan Eisman, our head of design um was leading that initiative. But really this was a lot about codifying the early ideas that made Slack great, especially from a product principles and and sort of craft perspective. And we started talking about this um and Noah had been at Slack early on and he 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 Stewart 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 and what it allowed him to do was reflect back to Stewart 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. Um, and and I think was a really really important part. And we worked with a lot of the sort of early Slack folks and the people that had really developed that culture, but it was folks who had really tried to grow and learn. They weren't trying to politic. They were trying to build great products.
Most people do not work for a Stewart that has incredible product sense, really cares about craft. Most people are like I he's so or she is so wrong about what we're doing. This is such a mistake. They don't listen. They don't know what they're talking about. One assumption I have of of how folks may misunderstand this skill is that they have to be a yes man. They have to take everything that the um 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.
Example: Elon Frank's Customer Anecdotes
Elon Frank who was my boss at Slack as well is now CPO of Checkr, 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 a strong enterprise background. so he could bring that to the forefront.
Curious Questioning to Co-Create
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 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?" 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 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 execs are so good at seeming certain. They say things in an authoritative way with confidence with shity 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 is 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.
I love these very tactical phrases and tips for how to deal with someone, say a leader, say you're, let's just say this is like, you know, they're a director of product, VP of product, CEO that you're trying to convince to agree to a plan. So, one phrase, the phrase you're suggesting here is, uh, that's so interesting. What led you to believe that? Um, anything else along these lines? Say you're pitching your product or an idea to say a VP of product and they're just like, what what else would what else what else works?
Understand Their Priorities Early
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 our 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 has Rachel been posting about lately? What what do you think is most important to her?" A colleague of mine, a peer on on our product leadership team trained a GPT on a bunch of um transcripts from past product reviews that are all publicly available. And we expect that our PMs are running their PRDs or their 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.
Early Alignment Conversations
And so I think that the 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 uh 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 uh we implemented something at Slack with Stewart because we realized we were coming to him with like done designs and he was like what the [ __ ] is this I this is completely different than how I had this in my mind so Ali Ray early Slack employee implemented something called hey Stewart 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. And 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. They're afraid to ask for more time to get that insight. But sometimes if you don't, you miss the point.
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 here's our options. Here's what I think is the right solution. And then at the same time, as you're describing, you want to come across as I want to learn. I'm not here to convince you. I'm here to just like help understand your worldview and where you think the right path is. How do you think about just those two kind of that balance of I have something I believe is right and okay but I'm here to learn and get your feedback and see what you think makes sense.
Avoid Overloading with Proof or Single Options
My advice on this may be a little paradoxical because um 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 tow too much upfront proof point. We talked 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 you 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 your work that helps elucidate why your solution is best. So, one of the mistakes I see people giving is 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 uh 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 we actually considered this.
Example: Product Review Feedback from Rachel Woolen
So we had a recent product review with my manager Rachel Woolen. uh she was a recent guest on how I AI and we uh 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 her 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 review is we said hey we really want to sort this out we want to get moving we want to show um
In a product alignment meeting, the team proposed a solution but faced pushback. They followed up by turning around a new doc in two days showing all options considered but not presented in the first review. The doc elucidated considerations, reasons why options would or wouldn't serve outcomes, and technical complexity. The executive then agreed, saying, "Oh yeah, okay. I see why the solution that you're proposing makes the most sense for what we're trying to accomplish."
Tactically, have options ready in an appendix or draft Figma file, even if not presenting all 15 initially. After design reviews with Stuart, the team implemented "Stuart plus two more": exactly what he asked for, plus two other versions they felt good about. This created a forum for conversation to debate merits of each approach.
Default: Don't lead with the whole process; have it ready if they don't buy in. Present options, then "here's my point of view, here's why I think this is the right one." Be ready for more options if they dig in.
Barbara Minto, first female consultant at McKinsey in the 1950s, developed the Minto Pyramid: present backwards to execs. Start with recommendation, then things explored, then evidence. Instead of process → conclusions → recommendation.
Gloss: People differ, so understand their preferred format, storytelling, pre-work. Some hate PowerPoint; some want only data, not qualitative research. Execs, tell people your preferences: e.g., "I prefer a doc. I want no upfront explanation. I want 10 minutes of quiet reading time and then we can come back together." Effective for busy people, short meetings, remote work.
- Understand how they respond best: presentation, recommendation + three options, data, five-minute fast conclusion + why.
- Ask people who know them what's top of mind right now; align if it's their big bet.
- Simulate them: feed previous meetings into a custom GPT and run your idea by it.
Hot take: Avoid "what's top of mind for you?" Instead, ask deeper: "Tell me how you spent your day," "What's the most urgent priority you're scared about messing up?" "What pressures are you facing?" With CEO: "What is the board pushing you on? What are the key inputs to your success?"
Execs want to succeed too. Align incentives: How does your proposal improve their metric, OKR, board pressure? Point out alignment. Model your world to amplify their success.
After chief of staff role, took over Slack's core product team (channels, emoji, search, messaging). Exec team felt loss of product craft mojo, "painting the insides of the cabinets" for 10x usability.
Implemented Customer Love Sprint: Entire engineering team stops for two weeks to paint insides of cabinets. Engineers pick what to work on (supported by PM, design, customer support); only rule: ship something good for users. Like a bug bash but exciting, with exec-judged competition. Shipped 65 improvements. Revived culture, aligned with exec beliefs on differentiation, user experience, growth.
Align pitch with their success: company goals like improve conversion, grow enterprise customers, brand perception, new category.
Inverse: Embed incentive structure in regular roadmap, team culture. Understand OKRs, positioning statement origins.
Everything should feel cohesive based on agreed outcome/mission. Use leading/lagging indicators or theory of change. Team may not directly move enterprise revenue, but exceptional experience leads to retention/conversion. Ensure metrics ladder up clearly, get exec agreement.
Enter with open mind: "That's so interesting. What led you to believe that?" Disarms exec, makes them comfortable to be honest.
Follow subtle threads/breadcrumbs: "I wonder if..." "Have you considered...?" Best people take the bait.
Example: CPO Rachel said, "We're going to have to think about design reviews." Head of Design Kev responded in an hour with Loom on framework: high-risk/low-risk design changes, blast radius, release processes for anyone shipping designs.
Recognized org incentives to empower, move fast. Negative example: In quarterly strategy review, Tamar repeatedly asked for top 10 use cases on X (4th time frustrated: "Why don't we have this documented?") People missed cue of importance underneath.
If you disagree, get more info on why they think it's important. Respond quickly to feedback; don't let go or exec loses faith.
To be more senior/leadership mindset: Act like CPO, come with solutions, follow threads quickly. Don't treat interactions as high-stakes by waiting too long—exec moves on. Keep ball rolling timely for excitement/brainpower.
Balance: Not every comment needs action. Ask: "How strongly do you feel about this?" "How urgent?" "Does this trump current priorities?" Often, they'll say no, backlog it. Execs move fast, don't always give urgency context.
Spend 30-60 seconds: "We're here to discuss XYZ. Last time, left off here. Goals today: ZYX. Here's how we'll run this meeting." Then stop. Add: "Was there anything else you hoped to cover?"
In doc/Loom read meetings, after leader's comments: Top section "themes for discussion." Bubble up biggest/controversial for live discussion. Answer offline: timeframe, staffing. Confirm: "Rachel, was that right? Did I get your thoughts? Anything to add?"
Influencing is your job: Get funding (eng/design resources) like VC money; deliver return. Buy-in makes everything easier, motivates harder work/purpose/support in other rooms.
Vanta automates SOC 2, ISO 27001 compliance, vendor risk. Completes questionnaires 5x faster. IDC study: Customers save $500,000/year, 3x more productive. $1,000 off at vanta.com/lenny.
They support you more. They talk about you in rooms that you're not in. It's the way you deliver great results.
Executives don't have the same boundaries of budget, headcount, and timeline. They can move people around, ask for more resourcing, get creative, elevate or kill projects. Approach them with: with today's resourcing, here's what I can get, but for the 10x or accelerated case, here's what I need to be successful. If it's not possible, tell them why: I'm super stoked about this, but I need eight more people, you twice a week for an hour, closer alignment with marketing. Identify constraints they can help with. People miss out on not asking for what they need, especially when the executive ask seems unreasonable.
If you get them excited enough, resourcing and prioritization can change significantly. Your job is to help them see the massive opportunity, unblock it, make it the new big bet.
Align with company goals and urgency. Adding a dozen people or perfect go-to-market alignment accelerates, but is it most important now? Stay rooted in company goals, exec priorities, user needs: to accelerate our goals, here's what we can do.
If you were in charge of a company, you'd be so excited if someone came to you with a 10x idea that's going to change the trajectory of your product.
Not every idea is big or great; they take time. In smaller organizations, build on your own if possible. For net new big ideas needing investment, build outside and around the executive. They want to hear from peers and experts why it matters. Get cross-functional alignment: customer success for expansion, marketing for 10x signups. Influence cross-functional execs and stakeholders to be advocates.
Build V1 prototype, messy version, get feedback, iterate, socialize to create groundswell of buy-in so exec can't say no to funding.
Biggest reason leaders don't buy in: different information. They don't see what you see; clarify on both sides.
April Underwood taught a tool: in product strategy meetings with Stuart, hold the whiteboard marker for back-and-forth. Understand deeply what they're seeing in market, feeling in business, instincts, then package into translatable, actionable framework. Marries leader's instincts with your synthesis to accelerate, combining what you know about the world with what they know.
Take it upon yourself to align your worldview with theirs. Ask: help me understand what I don't know; what led you to believe that?
Different phases: when new, less facetime. Time spent together accelerates trust, ability to speak freely, ask difficult questions, get real feedback. Ask for casual time, not always pitching, for real conversations. This groundwork pays dividends for later pitches.
Build trust by grounding in what they believe. If idea wildly different, don't bother; pursue nine others aligned with their beliefs. Engage from baseline assumption. Challenge once or twice with data, but if they feel strongly, drop it.
Long-term trust: hear them out, action past feedback, show results. Feed back impact: we worked with you, shipped it, here's results. Builds momentum for novel/scarier approaches.
From business book Switch on change management: shrink the change. Make scary/overwhelming into small experiment, one-week proof of concept. Easier to invest in small than six months uncertain.
Apply to product development: milestones, chunks showing outcomes/fit. Iterative approach with tools builds momentum, buy-in, trust for bigger things.
Reduce risk: two weeks low-risk easier to bite off. Identify feared risks: wasting time, time to market, not working with customers. Ask: what outcomes are you most afraid of? What would failure state be?
Red teaming: military tactic now in business, outsider's perspective. Avoid obsession with own thinking/prototype. Build trust by killing/deprioritizing things. Senior thinking, aligned incentives with exec for company/user outcome, not personal.
Everyone acquires resources/features; show: this is terrible, spent months, but kill because not working. Define how you'll know, decision date. Test, here's how we know it's working, back on X date.
Desire for certainty spirals out of control, especially now impossible. With engineers: I don't know if successful, check in on X date for next conversation. Certainty about check-in deescalates fears.
Execs have broad context: other product teams, E-staff conversations, executive roundtables. Extract that insight, apply to ideas. They want you to care, respect, apply it. Curiosity and empathy. Ask about their expertise; don't assume you know better.
Chief mistake: not caring, not taking into account to strengthen thinking.
There's a reason they're in this role. There's a reason you're not. Even if wrong, they believe right. Understand what they think/know.
To grow career: broaden context like they did. Peripheral vision. In senior rooms: domain expertise plus broad perspective on ecosystem, organization, industry. Seen as strategic thinker caring about company success.
Jessica pitched April Underwood as chief of staff to see if she wanted to be CPO. Still doesn't know—really hard job, more respect now. To grow into product leadership: expand viewpoint, global perspective.
Think on behalf of entire business, not just feature/goal. What business trying to do? How this fits? CEO thinking.
Example: Jeff Weinstein at Stripe, PM constantly tweeting/sharing Stripe as business, his work helping company. Jessica worked with him at Box. Charismatic, puts self in others' shoes.
Redid PM career ladder; led effort. Senior trait: product citizenship—embedding in organization, giving back best practices, mentoring, broadening horizons on tooling/technology/storytelling/strategy. Do at every level, connect dots to company importance.
Docs often: KR to ship thing—why matter? Tell story: business/user outcome making CEO excited. If not shifting outcomes/urgent, change course: not highest leverage, do X for broader goals.
Ultimate trust: tell leaders goal/ideas wrong, doesn't fit, kill product.
Think like a CPO. Put yourself in their shoes.
Stuart: CEO only one killing existing things, tough decisions. Culture mistake if not each thinking as owners/contributors/leaders, amplify business or save from itself.
Do the job you want versus the job you have.
Entering golden age of product management (not managers). Core skills: interesting ideas grounded in user empathy, curiosity, testing, iteration. In organizations, influencing for buy-in/funding V1 to expensive V2/3/4/ongoing 10x more important.
Execution complexity plummets, everyone builder. PMs/product thinkers leverage: synthesize to decide what survives/lives, encourage buy-in.
PM careers on type A, Gantt charts, best notetaker. AI better at data analysis, notes, experiments. Leverage shifts to deciding what work survives, getting buy-in.
Empowered to build V1 fast, momentum, signal on product-market fit/user benefit, faster cycles.
Influence, stakeholder management, learning are 10x skill.
Human brains necessary: deciding what to prioritize/build, alignment. Then build fast.
AI not anthropologist: based on existing knowledge. Best product thinkers: novel insights via user empathy, business dynamics, industry changes to prioritize what matters.
Flood of software; what works, matters, gets marketed/sold/final state requires buy-in.
Humans key: front-end prioritization, back-end judgment/taste if good/ready, distribution bottleneck. Flood of tools/products; attention to who? Marketing dollars, brand, customer base.
Example: Gemini/Google dominance via distribution tools.
Trust building with users and internal teams is underrated. Model companies are hiring at a huge rate, so people still work with colleagues and millions of users. Alongside distribution, trust is a function of influence and empathy.
Humans remain valuable, especially great product leaders who decide what to build and know when it's ready. AI is advancing rapidly: we never thought it would excel at coding, but soon 100% of code will be AI-written. Tools like Claude and Cursor provide excellent ideas for what to build—asking "what should I do to make this better?" yields 10 solid ideas.
As ideas proliferate with easy revisions (e.g., 40 versions of a 15-page strategy doc), decisions and building happen faster, but mistakes compound faster too. Strategy clarity becomes crucial to anchor empowered organizations. It defines shared beliefs, most important problems, where to invest time, energy, compute, and dollars—enabling teams to move at high velocity. Update this corpus frequently in the current fast mode to build the right things.
I love this point because there's a lot of talk on Twitter in the PM community about PRDs are dead and I think it's exactly the opposite which is being very clear about what we are doing and the strategy is now the most important thing because once you have that then it's cool fire off 100 agents and we'll go build it and launch it.
Strategy clarity is essential. Twitter debates like "PRDs are dead" or "software is dead" are dumb. What matters: understanding users, business and economic dynamics, strategy, and the right ways to execute together.
Agents like Claude and Cursor are now colleagues in the workforce. For identity, security, compliance, agents accelerate work but introduce risks where they fall short.
Everyone is a director of work with an army of agents—new junior team members without product philosophy knowledge. Onboard them by codifying: what's important as a product leader, product philosophy, product-market fit beliefs, success indicators, metrics. Analyze past successes and failures, train agent models with that data, history, context.
Also set guard rails: where to intervene on hallucinations, missteps; where unique taste, judgment, frame of reference require saying "Don't do this without me."
We're helping the agent learn the skills we've been talking about to influence you. Here's context on my goals. Here's what I understand about the customers. Here's our current priorities like help me tell me what to do and it's like influencing you to agree.
That's the singularity. Use agents as smart colleagues that never get irritated: poke holes in ideas, suggest alternatives, help plan, provide corporate context, amplify work.
Agents embody tips like coming in with an open mind: "Tell me more. What else?" They hop on ideas, generate many options.
Human brain chemistry struggles with the speed of ideas, change, building. We're not evolved for this pace. In Pachinko (history of a Korean family over generations), in the 1600s-1700s, two wives' daily routine: cook breakfast, market for rice/fish/vegetables, cook/serve/clean dinner. For most of history, that was the day.
Today's mental load is staggering. Use AI/agents to clear distractions, highlight important things. Make tough decisions: how much to focus on, allow for focus in ways good for humanity.
Jessica is a people person who loves in-person collaboration, whiteboard sessions, Enneagram 2-wing 3 (people person, communal thinker, achiever). Advice applies to all: shy/introverted, data-oriented/technical people can build trust and influence authentically.
Early career feedback: show up more aggressively/decisively "like a man." Realized her authentic style is her superpower. Focus on goals, growth in a true way—no need to mimic others.
You can accomplish the same things other people can through your own strengths. You don't have to do it the way they're doing it.
Books
Jessica recommends multigenerational historical fiction for windows into unfamiliar worlds:
- Pachinko: Korean family over generations, moving to Japan.
- Homegoing: West coast of Africa, slave trade impact, two split family branches.
- History of Burning: Indian indentured servants to Uganda for British railroad.
Host mentions The Overstory: family over generations around a tree (overstory as top branches providing shade).
Favorite Recent Movie/TV
The Pitt: vantage into emergency healthcare workers' difficult work, system stresses/brokenness, extreme care/love. Trending on podcast.
Favorite Recent Product
- $35 Amazon towel warmer: basket for towel, timer (30-60 min), brings household joy.
- Casa (getcasa.com, Bay Area expanding to LA): household assistant. Stocks paint colors/appliances/light bulbs; sends replacements (e.g., light bulbs, dishwasher options fitting space/quality via Amazon). Picks up packages/donations Fridays. Filter rotations (air purifiers, dishwasher, washer/dryer maintenance every 6 months). Monthly handyman credits.
Favorite Life Motto
Husband's suggestion: "First the guests"—rule with kids when hosting. Guests always go first: service, respect, welcoming, kind. Puts others first, brings joy, betters the world.
Related: Airbnb core value "be a host"; "If you want a village, be a villager"—build community, reach out, take first step.
Favorite Poster
Husband's music posters (he's a guitarist). Favorite: Jimi Hendrix plays the Greek (Greek Theatre, Berkeley, outdoor amphitheater on UC Berkeley campus with grass/blankets). Iconic musician, local culture access, music's importance.
Find Jessica on LinkedIn. Useful: share what resonated, past successes, how these show up in work; ideas for uplifting tech community amid AI change.
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