Why Influence Is the Product Skill AI Won't Replace: Jessica Fain on Winning Executive Buy-In
Lenny's Podcast
Jessica Fain has been a product leader at Box, Slack, Brightwheel, and now Webflow, and served as chief of staff to two of Slack's chief product officers. In this conversation with Lenny Rachitsky, Fain argues that influence, meaning the ability to build momentum behind good ideas and win the backing of executives, is close to the most important skill a product builder can have. Fain also argues that it matters more, not less, as AI makes execution cheaper. Fain's central claim is that most people misunderstand how executives actually make decisions. They center their own ideas instead of the executive's context, incentives, and constraints. Fain's remedy is to treat the executive the way a good product manager treats a user: with curiosity and empathy.
From Frustrated PM to Chief of Staff
Fain's interest in the topic started with frustration. As an individual-contributor PM at Slack, Fain would bring forward ideas grounded in what customers were saying. Some of those ideas generated excitement, funding, and a sense that the team could accomplish something great. Others that Fain believed in deeply "died on the vine." Fain felt they understood the user base well, but they couldn't see how decisions were being made behind the scenes.
At eight and a half months pregnant, Fain had a two-day overlap with April Underwood, who had just been named Slack's CPO and was returning from their own maternity leave. Fain worked up the courage to say they admired how April worked and thought, and asked to be considered if April ever wanted a chief of staff. When Fain came back from leave, they took that role, and later served as chief of staff to April's successor, Tamar Yehoshua.
The lesson from those years, in Fain's telling, is that people completely misunderstand what goes on in executives' heads, calendars, and incentive structures. Instead of understanding where the executive or stakeholder is coming from, people center their own desires, motivations, and slice of the world. Fain believes this hurts both their careers and the products they build.
The Executive Calendar as a Strobe Light
Fain's first example of this misunderstanding is the executive calendar, which is often blocked on Google Calendar so nobody can see what fills it. Fain describes it as a strobe light going off. An executive wakes up at 8 a.m. with a long list of urgent things, then moves from a finance meeting on budget to an interview for another executive, then a people problem, a legal problem, and a product review. The PM walking into that review may have been preparing for two, three, or six weeks. The executive probably hasn't thought about the topic since the last meeting and "may not have gone to the bathroom today." Everything that crosses an executive's plate feels like an emergency, and they haven't had the time or energy to focus on your problem.
Fain's most basic tactic follows from this. Take 30 seconds at the top of the meeting to explain why everyone is there, what happened last time, and why the topic matters. Fain adds that executives are optimizing for a global maximum across the company, while the presenter is usually optimizing locally for their own area.
Fain frames the broader goal as helping executives be their best selves. People focus on their own doc, prototype, or presentation, but rarely ask how to get the best thinking out of the executive. Fain says product leaders need to be "communication chameleons" who speak the executive's language. That means figuring out whether a given leader lights up at a design, a customer story, a dashboard, or an experiment, and then presenting in that form.
Treat the Executive as Your User
Rachitsky says he tells people he manages that it's their fault if leaders didn't buy into their ideas. Fain agrees, quoting Annie Pearl, their first PM manager at Box: "It's not my fault, but it is my problem."
Fain's core observation is that curiosity and empathy are among a PM's best skills, yet PMs drop them the moment they talk to an executive or stakeholder. They start thinking only about their idea, the approval, and getting to the next meeting. Fain suggests treating the executive as the key user and applying the same product skills to understanding them.
Fain calls going into a meeting just looking for approval "one of the most disastrous things you can do." The alternative is to go in asking how the executive's domain expertise, context, and experience can strengthen the plan. Fain says this yields both a better product and an executive who feels they built the product alongside you.
Fain is blunt about the common complaint that executives "just don't get it." If you don't respect the person or believe they know something you don't, Fain says you should quit and work somewhere else. If you do respect them and believe they got where they are by developing skills you want, then take the feedback, ask questions, and don't treat the meeting as a rubber stamp. Fain calls that a failure state, and one executives dislike.
Influence Is Not Politics
Rachitsky raises the objection that this can feel manipulative to people who just want to do great work. Fain distinguishes the two sharply. Politics is manipulating outcomes and people for your own gain. Influence is increasing the odds that your good ideas survive. In Fain's view, people who see this as politics are letting ego, and their own narrative and scope, crowd out empathy. Treating stakeholder conversations as discovery interviews turns them into learning.
Fain illustrates this with Noah Weiss, who succeeded Tamar as Slack's CPO. When Ethan Eismann, Slack's head of design, was leading an effort to write product principles that codified what made early Slack great, Noah pulled a small notebook out of their bag. It had a section of lessons they had learned from Stewart Butterfield over the years. Fain stresses that Noah hadn't kept it in anticipation of a principles exercise or to show off. It was genuine learning. That practice let Noah reflect Stewart's principles back while building their own product intuition, and it let the organization scale those principles. Fain says the early Slack people who shaped the culture were trying to grow and build great products, not to politic.
Disagreeing Without Being a Yes-Man
Most people don't work for someone with Stewart's product sense, Rachitsky notes, and often think their leader is simply wrong. Fain rejects the idea that influence means doing whatever the leader says. "You get paid to have an opinion. You get paid to be a domain expert." A good executive wants you to be the deepest person in the room on your topic.
Fain points to Ilan Frank, their boss at Slack and now CPO of Checkr, who always had a customer anecdote ready, along the lines of "I was just on site last week with so-and-so and they said…" Many Slack executives didn't come from strong enterprise backgrounds, so Ilan's enterprise expertise mattered.
That expertise has to come with curiosity. Fain describes a person on their current team who, on hearing something that contradicts the data or their experience, says: "That's so interesting. What led you to believe that?" Fain reads this as genuine curiosity. The person said something that seems wrong, but there must be something behind it. Asking opens the door to co-creating. Did they have a meeting last week? Are they getting pressure from the board? Fain notes that executives are very good at seeming certain, because so much of their job is making fast decisions with little information. If the executive is also a learner, unpacking why they believe something and then responding with your own expertise gets both of you to a better answer.
Learn What Matters to Them, Early
Fain's next advice is to understand the executive's belief system as early as possible. As chief of staff, Fain says, they could count on one hand the people who asked beforehand what the CPO cared about most before a product review. Fain recommends asking the executive's assistant, chief of staff, and people who have pitched successfully: what worked, what the executive is worried about, what the risks are.
AI makes this easier, according to Fain. You can ask Slackbot what a leader has been posting about lately. At Webflow, a peer on the product leadership team trained a GPT on transcripts of past product reviews, which are publicly available internally. PMs are expected to run their PRDs and pitches through it to see what Rachel Wolan, Webflow's CPO, is likely to push back on. Fain also suggests using AI on your own known weaknesses. If you've gotten feedback that your data or UX thinking is thin, ask for critique on that. Fain calls Claude "amazing for this."
The second step is to go in to learn, not to convince, and to do it early. Webflow has "office hours" for aligning on strategic direction, sometimes before a one-pager even exists. At Slack, teams had been bringing Stewart finished designs that didn't match what was in Stewart's head. Early employee Ali Rayl set up a format called "Hey Stewart, what do you think": half an hour to ask Stewart's beliefs and past experience on a topic, run like a user interview. Fain says people often fail by not asking for this time. They're afraid to take up busy executives' calendars, and then miss the point.
Having a Point of View Versus Showing Too Much Work
Rachitsky asks how to hold a point of view while going in to learn. Fain's answer is that people err in both directions.
The first error is showing too much work: "We talked to 16 participants from these 15 geos and this is statistically significant." Fain recalls doing exactly this in a review. The person they most needed to convince glazed over and got on their phone, and Fain says they "totally blew the meeting" by trying to prove they'd done their homework. The baseline expectation is that you did your job. Put the detail in the appendix.
The opposite error is offering only one option. Fain compares it to classic pricing strategy: present three options with a Goldilocks choice in the middle. More importantly, showing alternatives signals that you considered what the executive might think you missed. In a recent review with Rachel Wolan, Fain's team brought a single reasonable approach. It didn't match Rachel's expectations. The feedback, which Fain calls exactly right, was that Rachel couldn't see how the team was thinking about the possible permutations. The team asked to meet again in two days and returned with a new doc laying out every option they had considered, why each would or wouldn't serve the target outcomes, and the technical complexity of each. With that, Rachel agreed the proposed solution made the most sense. Fain's takeaway: you don't need to present all 15 options, but have them ready in an appendix or a draft Figma file.
At Slack, the team had a rule after design reviews called "Stewart plus two more." When Stewart specified exactly what he wanted, and Fain says Stewart usually had better ideas, the team built that version plus two others they believed in. This created a forum to debate the merits of each approach.
Rachitsky brings up Barbara Minto's pyramid approach: lead with the recommendation, then what you explored, then the evidence. Fain hadn't heard of it but thinks it works. Fain's caveat is that executives differ. Some hate PowerPoint. Some want only data and no qualitative research. Some will do pre-reads and some won't. Fain directly asks executives to state their preferences, for instance "I prefer a doc, no upfront explanation, ten minutes of quiet reading." Fain says that format works especially well for busy people, short meetings, and remote work, where presentations don't land well.
Skip "What's Top of Mind?" and Find the Incentives
Fain offers what they call a hot take: they dislike the question "What's top of mind for you?" It has become a trope, the title of generic weekly exec write-ups, and it draws neutralized answers. If you were researching users, you wouldn't ask that. You'd ask how they spent their day, what urgent priority they're scared of messing up, what pressures they face. Fain recently asked their CEO, "Tell me what the board is pushing you on." Everyone has a boss, Fain notes, including a CEO who seems all-powerful.
This leads to incentives. Executives want to be successful and good at their jobs too. Ideally your team's incentives already align with theirs. If not, Fain says you need that conversation, or you'll be misaligned from the start. If they do align, make the connection explicit: how does your proposal move their metric, their OKR, or the board pressure they're under? Fain adds that in product work, incentives shouldn't be reduced to promotions or not getting fired, though those are real. At best they're about making users successful, and through that the business. So you need to understand the executive's strategic beliefs about what will move the business.
Fain's example is from leading Slack's core product team (channels, emoji, search, messaging) after the chief-of-staff role. Leadership felt Slack had lost some of its "mojo" around craft, its habit of "painting the insides of the cabinets." The team launched a "customer love sprint": engineering stopped regular work for two weeks, engineers chose what to work on from ideas supplied by PM, design, and customer support, and the only rule was that each had to ship something good for users. Fain acknowledges this could be called a bug bash. The difference was making it a big, fun event, with a judging competition that executives joined. The team shipped 65 improvements and, in Fain's account, restored part of the culture and spoke directly to what executives believed differentiated Slack.
Fain extends the idea beyond new pitches to the regular roadmap. Understand how the OKRs and positioning got to be what they are, and embed that in the team's culture. The same applies to metrics. Using leading and lagging indicators, which the nonprofit world calls "theory of change," a team that can't directly move enterprise revenue can still show how its metrics ladder up to the company's beliefs about retention, conversion, or satisfaction, and get the executive to agree to that chain.
Following the Breadcrumbs, Quickly
Fain says many executive asks are subtle, such as "I wonder if…" or "Have you considered…?" Most people don't take the bait, and the best people do. Last week, Rachel remarked to Webflow's head of design, Kev, that as skills get democratized and everyone can design, ship code, and write PRDs, "we're going to have to think about design reviews at some point." Within an hour, Kev had a Loom proposing a framework: high- versus low-risk design changes, blast radius, release processes, and how anyone in the organization might ship designs to production. Nobody asked for it or set a deadline. Fain says Kev recognized the organization's incentive to keep people empowered and moving fast.
The counterexample is from Fain's own past. In a quarterly strategy review, Tamar asked for the fourth time to see the top 10 use cases on a topic. The fourth time, Tamar got frustrated that it still wasn't documented. Fain's interpretation is that people missed the cue that something important lay underneath. If you think the request isn't important, ask why the executive thinks it is. Letting it drop costs you their faith that you'll follow up on what they care about.
To show up as more senior, Fain says, "you have to act like a CPO": come with a solution, follow the thread, and do it quickly. Waiting a week on follow-ups means the executive has moved on. Keeping the ball rolling gets you more of their enthusiasm and brainpower.
Rachitsky raises the opposite risk: executives sometimes say things in passing that everyone treats as orders. Fain suggests asking how strongly they feel, how urgent it is, or whether it outranks current priorities. If they say yes, do it. Often, Fain says, they'll answer that it was just a random idea for the backlog. Executives move too fast to always signal urgency, so you have to ask. Fain admits that as a leader they are still working on labeling their own ideas as "just an idea" versus "a mandate."
Running the Meeting: The 60-Second Opening
Asked what the opening should contain, Fain gives a compact script: we're here to discuss X, last time we left off here, today's goals are Y, here's how we'll run the meeting. Then stop talking, because past 60 seconds you've lost them. Fain adds one more question: "Was there anything else you were hoping to cover today?" Rachitsky notes that "60 seconds" often turns into five minutes, and Fain agrees that you have to actually hold to it.
For Webflow's common format of silent reading or watching a Loom before discussing, Fain handles the flood of comments a leader may leave on a doc by adding a "themes for discussion" section at the top. It surfaces the biggest and most controversial issues that can only be resolved live. Questions about timeline or staffing can be answered offline. What can't be recovered is discussion time with that group. Fain checks with the leader ("Rachel, did I get your thoughts right?") and then moves to what Fain calls "the really good stuff."
It's Your Job, and Asking for What You Need
Rachitsky returns to people who resent this "meta work." Fain says it's literally the job. PMs get funding for ideas in the form of engineering, design, and cross-functional resources, which Fain likens to VC money from a CFO, CPO, or CEO who expects a return. Being a solo startup decision-maker is valid, but if you work with others, their buy-in makes everything easier. Beyond that, Fain says, motivated people who feel purpose work harder, support you more, and "talk about you in rooms that you're not in."
A further misunderstanding is constraints. Executives aren't bound by the budget, headcount, and timelines you feel. They can move people, ask for resources, elevate or kill projects. So when an ask seems impossible with your "pizza team" of four engineers, tell them why and say what you need: eight more people, an hour of their time twice a week, closer alignment with marketing. Fain says people miss this constantly, especially when the executive's request seems unreasonable. Fain still grounds this in company goals: would adding a dozen people actually do more for the company's priorities, or is something else more important?
On big ideas that get no traction, Fain says it depends on the organization and whether you can build it yourself. For large investments, the key lies around the executive. They'll want to hear from peers and experts. If customer success thinks it will accelerate expansion, or marketing thinks it will multiply signups, that cross-functional support helps. Fain notes PMs can now prototype a messy V1, gather feedback, and socialize it into "a groundswell of buy-in" that makes the funding hard to refuse.
Rachitsky suggests rejection often comes down to each side having different information. Fain cites a technique from April Underwood: in strategy sessions with Stewart, April always held the whiteboard marker. April drew out Stewart's instincts about the market and the business, while packaging them into actionable frameworks Stewart might not have had in mind. Fain also stresses relationship phases. When you're new, casual time together, when you're not pitching, builds the trust and candor that pays off in later pitches, and people undervalue it.
Building Trust: Shrink the Change and Kill Things
On trust, Fain's first advice is to ground ideas in what the executive already believes. If an idea is wildly at odds with their beliefs, "don't bother." You probably have nine other good ideas that fit better. You can push back once or twice with data, but if they still feel strongly, you probably have to drop it. Long-term trust comes from hearing them out, acting on past feedback, and delivering results. Reporting back that "we worked with you on this, we shipped it, here are the results" builds momentum for bolder proposals later.
Fain cites Switch, one of the few business books Fain likes, and its idea of "shrinking the change." Turn something scary into an experiment or a one-week proof of concept, so nobody has to commit six months up front. Fain applies this to any project longer than a month: define milestones and show outcomes along the way.
Fain recommends asking what kind of risk the executive fears most, whether wasted time, time to market, or doubt that customers will want it, and what failure would look like to them. Fain mentions red teaming, originally a military tactic, as a way to see your idea from outside. Fain says obsession with one's own idea is getting worse with prototyping. You build something beautiful you never could have built before and become unwilling to accept it might fail.
"One of the biggest things you can do to build trust is kill things," Fain says, or deprioritize them. It shows your incentives match the executive's concern for company and user outcomes. Rachitsky agrees, since most people only try to acquire more resources. Fain adds the structure: here's how I'll know it's not working, and here's when I'll come back with a decision. Many outcomes are unknowable, especially for AI-native products, and people crave certainty. A trick Fain learned working with engineers, who often want high certainty, is to say "I don't know the answer right now" but commit to a check-in date. At least the next checkpoint is certain, which Fain says de-escalates fear around an initiative.
Broad Context and Growing Into the Next Role
Asked about common mistakes, Fain points to the broad context executives carry. They know what other product teams are doing, what's discussed at the executive staff level, and what they hear at executive roundtables. Part of your job is extracting that and applying it to your ideas. Fain calls the chief mistake not caring about it.
That breadth is also how leaders get promoted. Keep your domain expertise, Fain says, but widen your view to the whole organization and industry, and you'll be seen as a strategic thinker who cares about the company's success. When pitching April on the chief-of-staff job, Fain said they wanted to find out whether they wanted to be a CPO someday. Fain still doesn't know, calling it a very hard job they respect far more now.
Rachitsky offers Jeff Weinstein at Stripe as an example: a PM who constantly thinks and posts about Stripe as a business. Fain, who worked with Jeff at Box, agrees and describes Jeff as charismatic and good at taking others' perspectives. Fain recently led a rewrite of Webflow's PM career ladder, which names "product citizenship" as a trait of seniority: giving best practices back, mentoring, and broadening others' horizons on tooling, storytelling, and strategy. Fain says they often see docs whose key result is "ship this thing" with no explanation of why it matters or why the CEO would care. The flip side, if your work doesn't move an important outcome, is to say so and propose something more effective. Fain references Stewart's comment on the podcast that CEOs are often the only ones who can kill existing things, and says it's a cultural mistake if others don't also raise such opportunities to "amplify the business or save it from itself."
AI: A Golden Age of Product Management, Not Product Managers
Fain believes we're entering "a golden age of product management, not of product managers." The core skills of user empathy, curiosity, testing, and iteration matter more than ever. Organizations still need buy-in to fund not just a V1 but the costlier V2, V3, and ongoing support, and Fain says that becomes ten times more important. PMs have long built careers on being type-A Gantt-chart masters and the best note-takers. If AI beats you at analyzing data, taking notes, or running experiments, Fain says, leverage shifts from doing and synthesizing work to deciding what work survives and bringing others along. Fain finds this exciting because PMs, engineers, and designers can now produce a first version and get signal on product-market fit much faster. Influence, stakeholder management, and learning are "the 10x skill."
Fain says AI isn't yet a good "anthropologist." It draws on existing knowledge, while the best product thinkers reach novel insights through user empathy and understanding of changing business dynamics. "We're going to have so much software we won't even know what to do with it." The question is which software matters and gets marketed and sold. Rachitsky lists where humans stay necessary: deciding what to build, judging whether it's ready, and distribution, which he calls an underappreciated new bottleneck. Fain agrees strongly. Fain doesn't believe everyone can build the next Salesforce alone, and argues that attention will still go to whoever has marketing dollars, brand, and customers. Fain cites Gemini and Google's tools as the quintessential distribution example. Fain adds trust, with users and internal teams, as equally underrated, noting that even model companies are hiring heavily.
Rachitsky pushes back that people underestimate how good AI will get at judgment too, since Codex and Claude Code already give him good ideas for what to build. Fain responds that as ideas multiply, mistakes compound faster. Webflow's current strategy doc rewrite is on about 40 versions because it's so easy to revise a 15-page doc. That's why strategic clarity matters more: a shared, frequently updated set of beliefs about which problems deserve time, compute, and money lets teams move fast and build the right thing, "as opposed to just the idea that Claude had." Rachitsky ties this to Twitter claims that PRDs are dead, which he thinks are backwards. Fain calls such takes "really dumb" and "a little insufferable," saying what still matters is understanding users, business dynamics, and strategy.
On agents as colleagues, Fain says we are all "directors of work" now. If a hundred agent colleagues joined your team, you'd need to onboard them as you would junior staff who don't know your product philosophy. That means codifying what you believe about product-market fit, success, and metrics, analyzing your past wins and failures, and feeding that context in. The other half is guardrails: where you must catch hallucinations or missteps, and where your taste and judgment mean "don't do this without me." Rachitsky observes that this is essentially teaching agents to influence you. Fain describes using AI as "a really smart colleague that never gets irritated by our questions": poke holes in my ideas, tell me what you'd do differently, bring in more corporate context than I could read myself.
Fain is also concerned about protecting our brains from overwhelm. Fain describes a passage in Pachinko where, in an earlier generation, two women's day is cooking breakfast, going to market, cooking, serving, and cleaning up dinner, which Fain says was the shape of most of human history. The mental load now is "staggering," and Fain thinks one important use of AI is clearing distraction and surfacing what matters most. People will need to make hard choices about how much they can actually focus on.
Influence on Your Own Terms
Fain closes the main conversation with a point about authenticity. Fain identifies as a people person, an Enneagram "two-wing-three," which Fain describes as a mix of the communal people person and the achiever. Fain hears people dismiss the advice with "you're just good with people." Fain's response is that influence and trust-building aren't tied to one personality type. Someone shy, introverted, data-oriented, or deeply technical can build influence in a way that feels true to them. Early in their career, Fain was told to show up "more like a man would," more aggressive and decisive. Fain grants there were useful nuggets in that feedback, but says it took a while to see that their own way of showing up was a superpower to double down on, rather than something to replace by imitating someone else.
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 Brightwheel 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. I am very excited for you to learn from Jessica.
Before we get into it, don't forget to check out lennisproduct.com for an incredible set of deals available exclusively to Lenny's newsletter subscribers. Now, let's get into it after a short word from our wonderful sponsors.
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Jessica, thank you so much for being here. Welcome to the podcast.
Thanks for having me. It's my pleasure.
Let's set this conversation up. We're going to be talking about the skill and the art of influence and in particular influencing executives and leaders, people above you that you want to convince to do things you want them to do. Help us understand why this is worth people's time. Why is this worth the next hour of someone listening to this? Why is this skill so important to people's careers?
I think as product builders, there's almost not a skill that's more important. Influence and building a 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.
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 going to do amazing work. It's going to show itself. Everyone's going to recognize it. And you just run into this wall of like, oh man, all these other people are getting promoted. Maybe talk about that because it feels like that's a big trap people run into.
I think why I wanted to talk to you about this is, you know, when I was an IC PM, 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. 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 Tamar Yehoshua, who succeeded April,
who's been on the podcast,
who's been on the podcast, right? And is now a CPO and head of AI at Atlassian. Tamar, don't be mad if I mess up your title. And what I learned through that process is that people completely misunderstand how executives make decisions, what is going on in the heads, in the calendars, in the incentive structures of executives. 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.
What's an example of that when you talk about people don't understand how product leaders actually make decisions, how they decide what to do, what to listen to. What's an example?
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 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.
Essentially, this is how to help someone in this world that is running around from meeting to meeting without context on most things, maybe hasn't had time to go to the bathroom. How do we help them see what you want them to see and maybe buy into your vision and suggestions?
Yeah, I think that, you know, one of the ways that I phrase 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 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? 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, 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 dive into it.
The other thing I always tell people I managed is it's your fault if the leaders didn't buy into your idea. You can't just be like, ah, they just don't see it. It's not my fault. They agreed to do something else. I always tell them that's just you're not able to influence them and convince them that you're right.
Yeah. And Annie Pearl, who was my first PM manager back at Box, she's
also former podcast guest.
Also former podcast guest, a former CPO at Calendly and 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 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.
You know, I think 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.
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." 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.
I want to dive deeper into this stuff, but first something on my mind is some people might be turned off by this topic in terms of it may feel icky of just like, I don't want to try to be this manipulative person and, you know, deal with politics and influence. I just want to do awesome work. Why do I have to do this? Speak to that person that kind of just feels icky about building this and working on this and being this person.
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-ego way... I'll give an example here. Noah Weiss, who succeeded Tamar Yehoshua as CPO of Slack and also former podcast...
What a run we're on here.
Oh, no. Yeah, I've learned so much from Noah. We sat down to write product principles for Slack, and Ethan Eismann, 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 a 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 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 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. And I think that 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. And that's the approach we have to take.
Okay. So, what if you're not working for Stewart, which most people, you know... Stewart, also former podcast guest. I feel like just the alumni of Slack, holy moly. Just the fact that I have so many of these people on the podcast. What a sign of an incredible team. Okay, so
Yeah. So most people do not work for a Stewart that has incredible product sense, really cares about craft and, you know, most people are like, 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. How do you deal with that?
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, Ilan 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.
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 a guy on my team does super, super well right now. You know, he'll hear something that flies in the face of 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 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 certainty, 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.
I love these very tactical phrases and tips for how to deal with someone, say a leader, let's just say this is, 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, "That's so interesting. What led you to believe that?" 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 else works?
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 do you think is most important to her?" A colleague of mine, a peer on our product leadership team, trained a GPT on a bunch of transcripts 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 the weaknesses in these 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 Stewart 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 Ali Rayl, 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. You know, this is sort of in 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.
Something that we hear a lot on this podcast is, as a product leader, as a leader of any kind, you want to have a point of view. You want to come into a discussion with, here's our options, here's what I think is the right solution. 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 help understand your worldview and where you think the right path is. How do you think about that balance of, I have something I believe is right, but I'm here to learn and get your feedback and see what you think makes sense?
Okay. So my advice on this may be a little paradoxical, because I think people make mistakes in both directions on the poles here. On the one hand, I think there's an error people make of trying to show too much work, trying to show too much upfront proof point. "We talked to 16 participants from these 15 geos and this is 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 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 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, we actually considered this.
So we had a recent product review with my manager Rachel Wolan. She was a recent guest on How I AI. And we 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 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 considered, 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 Stewart. We'd go through the design review and he'd say, "No, do it exactly like this. I want, you know, 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 "Stewart 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.
Awesome. Okay. So, there's a bunch of advice here. One is, the default is don't go in with here's our whole process that landed on this suggestion, but have that ready because they may ask for that if they don't buy into it. Another is present options. And then there's a, here's my point of view, here's why I think this is the right one. And then if they dig in, be ready for more options. Have you ever looked into the Minto pyramid way of presenting stuff?
No, I don't know what that is.
Okay. So, there's this lady, Barbara Minto. She's like from the 50s, I think she was the first female consultant at McKinsey or something like that, and she kind of figured out the best way to present information to execs is backwards, essentially. It's, instead of here's our process, here's all the things we did, here's our set of conclusions, and then here's our recommendation, it's flip it. Start with here's our recommendation, and then here's the things we explored, and then here's the evidence behind that. Feels like that's kind of what you're describing.
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 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 [ __ ] 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 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 pre-reads, 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.
So, there's a bunch of tips here that I want to summarize for how to kind of set yourself up for success. One is what you just described, which is just think about how do they respond best? What kind of setup do they respond best to? Is it a presentation? Is it a here's what we recommend, here's three options? Is it data? Something else? So, there's just understand here's what this person likes. They want like a five-minute fast conclusion. Then there's your advice of ask people that know them what is top of mind for them right now, because they may be like, this is the big bet we're making right now, if it's not aligned with that, they're not going to care. So either ask them or ask people around them what's top of mind for them right now. And then there's this idea of almost simulate them. Feed all the previous meetings with them into, say, a Claude project or something like that, create a little GPT, and run your idea by them, and like, what would you say?
I will tell you, I am not a big fan of the "what's top of mind for you" question. This is a hot take, because I think that what often people do is they think through their top priorities, their top experiences. 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, and even a CEO who seems so powerful and competent 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 execs want to be successful, too. They want to be good at their jobs. And how can you help them? I mean, in the best case scenario, your incentives at a local team level or product organization level really closely align with their incentives, that you're working on something that really matters to the company. If you're not, you really should be having that conversation, because you'll be in misalignment from the start. But if you actually have alignment, point out that alignment. How is the metric that they're trying to move, the OKR they're responsible for, the board pressure that they're under, going to be improved by the thing that you are proposing, and how do you get there together? So I think that 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?
Okay, that is such an important lesson. Before I follow that thread, just to clarify this question of what is top of mind. Your advice was ask people around them what is top of mind for them. Don't ask them directly this question.
Top of mind has become this sort of trope, right? Execs write 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's the spicier question that'll get a more interesting answer.
So then, but going back to this incentives piece, such a powerful lever for getting anyone, basically, to agree to what you want, which is what are their goals? What are they
trying to do? How are they measured? How's success for them? And then how's the thing you're pitching them aligning with that and will help them achieve that specific goal.
Right? And in a product, 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. And we talked about, you know, 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 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 gotta fix these, you know, these rough edges, these misses in the product," but we 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.
Okay. So to summarize the kind of tactics so far, one is align your pitch with the person you're trying to pitch's incentives. I don't know if the grammar on that sentence works, but what are they trying, what does success look like for them? Connect the thing you're pitching them with that success.
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, you know, 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 exec team, our leadership has said is important.
So basically everything should feel like it's a cohesive set of priorities based on some outcome you all agreed to in the mission.
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 retention, 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.
Okay. And then a second lever is trying to not go into a conversation, even though you are trying to influence them. It's to go into it with an open mind and a learning mindset. You use this phrase, "That's so interesting. What led you to believe that?"
Right. 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? You want them to feel comfortable. You want them to feel like they can be honest with you. I think something I see people miss often is they don't follow the subtle threads that executives lead them, the sort of breadcrumbs of opinions. You know, in a sort of more clear-cut scenario, your leader, your executive will say to you, "Okay, I'd like a brief on exactly this thing. Write it generally this way. Let's review it in a week." That's a very clear-cut ask, but very very often the asks are more subtle. I wonder if, I'm thinking about, have you considered? And what I find is that people don't take the bait, 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 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, 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 subtle feedback they're giving. You know, 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 cue that there's really something deep underneath. There's really an important piece of feedback or a question that they're not 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.
It also sounds like a really good way to influence is you take the reins, and here's where I think we could go with this, and here's the answer to your question.
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 stakes, 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.
And obviously there's like, you know, everyone's so busy, there's already so much work on their plates, you can't just hop on everything an exec says. There's also this like classic advice of sometimes execs just say something and everyone takes it so seriously. Oh, I have to do that. And sometimes they're just saying it in passing. So, it's probably all, you know, it's a balance of like take the opportunities, don't hop on every single thing.
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?" 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.
This comes back to your point about getting into the mind of the person in the meeting, the leader. They're running around all day. I think you call it a strobe. You're just like bam, another meeting, next meeting, next meeting, next meeting, without a lot of context, and they just say things, and sometimes it's important to them, sometimes not. Which comes back to one of your tips at the beginning of this chat, is spend 30 to 60 seconds at the beginning just giving them a little context on what the heck. What would you recommend in that 30, 60 seconds? What are some kind of key bullet points of what you want to communicate?
Yeah, in 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?
That was awesome. I love this advice. I am excited to tweet this out, just to summarize these bullet points you just shared. That is so cool. I love that. And to your point, if 60 seconds flies by, you may think you're talking for 60 seconds. It often ends up being 5 minutes. So the advice of keep it under 60 seconds, just like try to actually do that.
Try to actually do that. I think the other thing here is, you know, 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 time frame for this, what's the staffing need for why, I can answer offline, I can answer in a follow-up. What I can't get again is the time for discussion with that group. And the safer that they feel in that discussion, and the more that they think that you've understood what is the most sort of spicy or controversial, that's where you get to the good stuff and you really get their insight and input. So I, you know, put a section at the top and say topics for discussion, that I'm reading through the comments. Rachel, was that right? Did I sort of get your thoughts right? Anything you would add to this? And then we can talk about the really good stuff that gets us to a better outcome.
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We've talked about aligning your incentives and goals with their goals, going in with an open mind, setting context at the beginning of the meeting, understanding how they like to be presented to. What else can we learn to become better at influencing execs? And let me just do a quick tangent. As people are listening to this, they may again be like, "Oh my god, all this BS I have to do. I just want to do awesome work. Why am I spending all this time learning all this meta work of how to convince someone of a freaking thing? I just want to build awesome products, drive, you know, growth for the business and the product, and this sucks." I think it's again important to remind people this is just the way things go. You need to influence people in power to agree with your approach. That's just the way it is. You can't just be like, "Nah, no one understands me. It sucks. So, it's not my fault."
I mean, it's literally your job, right? 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? 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? And 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 will 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.
I think that's such an important framing. Okay. What other tactics, what other techniques work in helping leaders get influenced?
Yeah. Get influenced. I love that. I love that.
Yeah, we should have like a stamp like 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, 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 know 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 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.
This is such a good piece of advice of just if you get them excited enough, things can significantly change in terms of resourcing and prioritization. Like your job is to help them see how massive an opportunity this is and go and not just give you what you want, but just like wow, okay, here's the way to unblock this thing. Here's how we can go. Like, okay, this is going to be our new big bet. Let's go big here.
Yeah, absolutely. This is going to be our new big bet. And this comes back to aligning with what the company's trying to accomplish. And also the urgency. So some things if you added a dozen more people or perfect alignment with go to market, yeah, you could get them to market faster, but is that the most important thing for the company goals? Is right now the answer 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, in what the exec is trying to accomplish, in 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.
Like you know 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, like that's what everybody wants. And so that is a really powerful way of approaching all these things. Obviously not every idea is going to be a big idea. Not every idea is a great idea. A lot of times these take time. Also maybe speak to that, just like say you have a big idea and they're like nah. What are some expectations to set for people that come up with a big idea that just isn't getting any traction?
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, you know, a large scale investment.
I think the real thing about building toward a big idea, towards something net new, the key is really outside and around the executive. So if the executive is the decision maker on whether we're going to invest here, they also want to understand from their peers, from other experts why this actually matters. If you have something net new that you want to bring to market and customer success thinks it would really accelerate expansion rates or you know the marketing team thinks that signups would be 10xed because of this, if you have that cross-functional alignment. And this is where a lot of these lessons don't just apply if you're going into a product executive meeting, but if you're influencing your cross-functional execs and your cross-functional stakeholders to be advocates on your behalf.
I think that, you know, we now have more tools than ever as product folks to build out the V1, right? Prototype something, build your own app, build the messy version of it, get feedback, iterate, and be socializing that in a way that creates a groundswell of buy-in, to the point that, you know, the exec can't say no to the funding.
Along those lines, it feels like to me the biggest reason that a leader doesn't buy into your pitch is you just have different information. They don't see what you see. You don't see what they see, right? They have all this other stuff that they're looking at and trying to decide. Maybe speak to just that skill of trying to clarify information on both sides.
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 know about the world and what they know about the world.
So what I'm hearing is kind of take it upon yourself to help them to kind of align your worldview with their worldview. And there's this question coming back, just like help me understand what I don't, what was the question you had? Oh, that's so interesting. What led you to believe that? Like these are kind of questions that help you extract what you don't know that they know.
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 upfront spent together because it pays dividends for the later pitch.
Yeah, I'm glad you went there. That's exactly where I was going to actually go, is this idea of trust and building and having, you know, giving the person a reason to kind of assume that you know what you're doing. Obviously hard to build trust. And the reason I think this is important is sometimes you have the best idea and they just don't buy it because they just don't know what you've been up to. They don't know how awesome you are, how smart you are, how successful you've been your whole life and career, maybe because you're new. What are some tips for trying to build trust with the leader so that these things become easier?
I 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 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 results." 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 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.
That's an awesome, very tactical piece of advice here, to convince someone to do something is just reduce the risk, essentially reduce the investment to help build trust in okay, this is showing success, because obviously it's much easier to bite off on something that's going to take two weeks or have very low risk and impact if it's not a good idea.
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?
You know, 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 obsessed with your own thinking, with your own concept? Because so often we get wrapped around the axle. I actually find this happens even more with prototyping. You build a prototype and you're like, "Oh, looks so beautiful. I would have never been able to build that before." That's actually not a very good idea, but you get obsessed with it and you're unwilling to accept that it could fail.
I think one of the biggest things you can do to build trust is kill things, deprioritize things. That is a very very senior way of thinking, right? And it shows that you have the same aligned incentives as the executive who's thinking about the good of the company outcome, the user outcome, and not just your own.
That is such a good one because everyone's always just trying to acquire more resources, more investment, just like more features, and showing that, okay, this is a terrible idea. I know I spent like months on this, but no, we should kill this because it's not working,
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, 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. You know, 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 tool for sort of de-escalating the fears and risks around a given initiative or idea.
Okay. Before we get into AI's impact and all this stuff, are there any other common mistakes people make when they are trying to get better at the skill of influence or just any other really powerful tactics for increasing your ability to influence leaders?
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 coming 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 executives. 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.
Yeah. So much of this is about just coming into it with like, here's what I, it's just like having the same information. And I think this point about just believe they know what they're doing is so underappreciated. Like there's a reason they're in this role. There's a reason you're not there. There's a reason this company's doing as well as it is. And even if they are wrong, they believe they are right. So it's important to understand what they think and know and what information they have access to.
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 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 say it. 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, 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. But I think that if you want to grow into a product leadership role, expanding your viewpoint, expanding the way that you see problems and thinking about it from a global perspective is a way to show up as that strategic leader that you say you want to be.
I love this advice. Just to make it very clear for people, because it's easy to just like, yeah, okay, I'll just like expand my horizon. Like basically the advice here is just like think on behalf of the entire business, not just your feature, not just your little goal. It's like, what is the business trying to do? Here's how this fits into it. Here's what the CEO broadly is thinking about. Like the epitome of this to me is Jeff Weinstein, I think is how I pronounce his last name, or Weinstein, at Stripe. Like he's just like a PM on a product and he's just constantly tweeting and sharing Stripe as a business. Like he's just thinking about Stripe as the company and then here's this thing I work on that helps the company.
Absolutely. And Jeff and I work together at Box.
Oh, you did? Oh, that is so cool. Right. Okay. Would you agree he's like the epitome of this?
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. 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 KR, sometimes that's the case, right? But even if that's true, why are you doing that? What is the outcome for the business? Why would the CEO be excited about shipping that? It's usually because of some business outcome or user outcome that you have to tie back to their perspective of. And then I think the flip side of it is, if you're working on something that doesn't shift one of those outcomes or isn't urgent for the business, 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."
That's where I was going to go, is just like that's the ultimate trust-building move, is to tell the leaders, okay, here's our goal, here's all these ideas, but we don't think this is the right goal, and here's how this doesn't fit in, and here's why we should kill this product.
Right. Exactly. Right. Think like a CPO. Put yourself in their shoes. I mean, you had Stewart on a few weeks ago and he talked about how the CEO is kind of the only one who can really kill things across a, you know, 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.
Do the job you want versus the job you have.
Classic.
Yes.
Okay, let's talk AI. I feel like you cannot do anything these days without mentioning AI in some way. How is AI changing the skill of influence? What's changed in the past couple years in trying to convince people to do the things you're hoping them to do?
I think that we are entering a golden age of product management, not of product managers, but of product management and the core skills that made this function the thing that I love to do. You know, 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 and product thinkers, which I think is far beyond the product management function, can be so incredibly influenced by those core 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 notetaker in the business. And 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 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 act of influence, the act of stakeholder management, the act of learning is the 10x skill.
Awesome. This is such a fun topic. The way I've been thinking about this is just like, where are human brains going to continue to be necessary and useful in this new world?
I'm terrified. [laughter]
Maybe nowhere.
Maybe nowhere. But the way you described it, which I totally agree with, is essentially it's deciding what to do and getting everyone on the same page, alignment around that. Here's, we're all on the same page. Here's what we're prioritizing. And then it's like, cool, now let's build it. And that happens so quickly now.
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 gonna 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 to that idea working.
Yeah. The way I think about this right now is just like, where humans are still necessary and great product thinkers are still necessary is on the front end, deciding what to prioritize and build; on the back end, determining if this is good and ready, essentially judgment and taste; and then there's distribution, I think, is such an underappreciated, like, new bottleneck, because as you said, there's so much [ __ ] out there. Just like, how do we get anyone to pay attention to any of this stuff? Every day there's like a new life-changing product. So, I feel like that's going to be a big problem.
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 know, 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 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. You are still working with millions of users, and alongside distribution is trust, and that is a function of influence and empathy.
Along these lines, what I wonder is, we talked about these other two kind of areas where humans are still valuable and great product leaders are still valuable: deciding what to build, knowing if it's ready and awesome. I wonder how good AI will get at those things, because we never thought AI would be amazing at coding and now it's, 100% of code will soon be written by AI. And I've actually been building a bunch of stuff and I just find Codex and Claude Code are so good at actually giving you ideas for what to build. I'm just like, what should I do to make this better? And it's like, here's 10 ideas, and then they're like, that is a really good idea. So, I think it'll get there. People underestimate how good it'll get at these things, I think.
Yeah, I do think that as ideas proliferate and as there just becomes 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 at as fast a velocity as 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 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.
I love this point because there's a lot of talk on Twitter, actually just today, 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.
Totally. Strategy clarity is so, so important. I am not in the Twitterverse. 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.
Okay, maybe one more question along these lines, just agents now running as colleagues. Everyone's got all these Claudes running, Codexes, all kinds of agent platforms. Now that agents are a part of kind of the workforce, and increasingly, is there anything there around influence that is valuable for people to start thinking about, to learn how to do?
I 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 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"?
What's so funny about this, essentially, 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.
Absolutely. I think, 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 and AI 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.
Oh, it's like so interesting. Like one of your, you know, tips is come in with an open mind and learn. It's like exactly what an agent does. Tell me more. What else should I... and then just like hopping on your ideas, like okay, cool, we'll add that to the two. Like all the ideas you've shared, agents are so good at. So that's, yeah.
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 diseolved 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 and agents 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?
What a time to be alive, Jessica. Holy... Oh my god. Before we get to our very exciting lightning round, is there anything else that you wanted to share? Anything else you want to double down on?
One thing I think that I'll say is I'm a people person. I love in-person collaboration and I love talking ideas through and whiteboard sessions. I'm a two-wing three, if there are any other Enneagram fans out there. It's a mix of the people person, the 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 Jess, you're good with people, or 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 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, 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.
I could not agree more with that. I've shared very similar sentiment on the pod a few times. Just like, 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.
Exactly. I so agree.
A beautiful way to end that. And with that, we have reached our very exciting lightning round. I've got five questions for you. Are you ready?
I'm ready. I'm so excited.
What are two or three books that you find yourself recommending most to other people?
I think there's a genre of book I've really fallen in love with. I mentioned Pachinko 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 just loved, which is multigenerational 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 the impact of the slave trade, and the ongoing life in Africa from two split parts of the family. A History 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 I really treasure that sort of window into a different world.
I think the book The Overstory is an example of that. Have you heard of that?
No, I haven't.
I think I might be getting it wrong, but it's called The Overstory, which is around a concept of, when you have a big tree, the overstory is the branches that kind of sit on top that kind of create a shade.
Oh, that's beautiful.
That's the book I'm thinking about, and it's the story of a family over many generations and around a tree.
Oh, great. Now I have to pick that up.
It was popular. Okay. If it's the one I'm thinking about, I think you're going to love it.
Okay, great.
Favorite recent movie or TV show you've really enjoyed?
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 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 has just given me so much admiration.
It is trending on this podcast. So, and I'm watching.
It's really good.
It is really good. Okay. Favorite recent product, favorite product you've recently discovered that you really love.
Okay. I bought my husband a towel warmer. It was like 35 bucks 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.
I want one. That sounds amazing. Does it sit on top of an existing towel rack or is it a separate thing that you...
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.
Okay. I love this idea. Never been mentioned before.
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 a Casa 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. And 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 thrive.
I love that pick. I was looking up their domain name, getcasa.com. And I think they're only in the Bay Area right now, and I think they're expanding into LA right now.
Expanding into LA. Yep.
Sweet. That's a good pick. And their website is very bare. I don't even know how you sign up, but yeah, I don't know. I guess you could figure it out, but I love Casa. Yeah, they also do like a filter rotation thing. So like every six months they come and replace all your filters for air purifiers and whatever.
You can set maintenance for your dishwasher, for your air filters, for your washer dryer, which has been super cool to see. 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.
Awesome. Okay, two more questions. Do you have a favorite life motto that you often come back to in work or in life?
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 guests. So if you have guests over, which we love to host people in our house, our rule 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. When you are of service to others, when you are inclusive, when you can put them first ahead of yourself, I think it actually brings a lot of joy to you. And it certainly makes the world a little bit better.
Oh, one of the core values at Airbnb was "be a host."
Yeah.
Which is very appropriate for Airbnb, but such a broadly useful lens.
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.
Final question. You have some cool posters behind you, if people are watching on YouTube. Is there one that's a favorite? Is there one that has a story, per chance?
Ah, 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...
It is such a cool venue. Just, if people don't know, it's just like this outdoor amphitheater with grass. You can get blankets.
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.
Well, with that, Jessica, thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out, maybe follow up on anything here? And how can listeners be useful to you?
I am not a very online person, which is, you know, 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 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.
What change are you speaking of? [laughter] Nothing.
It's called AI. We're still talking about AI.
Oh, man. All right. Well, Jessica, thank you so much for being here.
Yeah. Thanks.
Bye, everyone.
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
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