Why Half of Product Managers Are in Trouble: Nikhyl Singhal on Builders, Judgment, and the Courage to Reinvent
Lenny's Podcast
Nikhyl Singhal is a former product executive at Meta, Google, and Credit Karma, a four-time founder, and the founder of The Skip, a community of about 125 heads of product. In his second appearance on Lenny's Podcast, he tries to answer a question many product managers are asking: what is actually happening to their profession, and what should they do about it? His answer is blunt. The next two years will be chaotic. The people who love building will "have the time of their lives." The roughly half of product managers whose main skill has been moving information are "in trouble." The deciding factor, he argues, is less about talent than about whether people are willing to cross a psychological threshold and start reinventing themselves.
Three years ago: responsibility without authority
Singhal starts with the period of his first appearance, around the end of COVID, when the zero-interest-rate era was cresting. The industry was then the biggest it had ever been, with more product managers and CPOs than at any point in history, and people were well paid. Even so, he says, the product leaders he talked to at the time "weren't very happy." Their days were mostly spent moving information: reshaping how their team presented something to their boss so that the boss could reshape it again for their own boss. The function had become focused on "responsibility without authority," which he calls the greatest form of workplace stress.
People today talk mostly about new worries, such as whether AI will replace their function. Singhal's point is that anyone who has been in product for a few years should remember how hard that earlier period was.
A renaissance that comes with exhaustion
What has changed, in his view, is that product people are having fun again because they can build. They depend on fewer people to have impact, and their ideas connect more directly to testing and to customers. He calls this "a complete renaissance for the product industry." Among the strongest builders in his network, he reports that compensation is at an all-time high, offers are more plentiful than ever, and many see their next role as founder, CEO, or a C-level job outside product.
He is just as direct about the cost. He says he has "never seen an industry that's more tired than they are now." Once, people could learn their job and be fine for a decade before becoming a manager. Now, if you fall three months behind, colleagues tell you the team stopped doing that thing three months ago. Even PRDs are questioned, and "everyone's in a state of alert." At the same time, large employers are cutting tens of thousands of people while also hiring and paying triple wages. Which side of that you land on shapes how you see the whole situation.
He singles out mid-career people, roughly those in their 30s, as especially strained. These are their "power years": they finally know what they are doing. They are also settling down, having kids, watching their parents age and become dependent, and dealing with their own health for the first time. Work already takes whatever time is left, and now it also changes constantly: "what's the latest in Claude Code? They changed it this morning." There is joy, he says, "but there's fatigue in a way that I haven't quite seen before."
Asked whether product leaders are better or worse off than two or three years ago, he separates how people describe it from how he sees it. He measures "doing better" by how much choice people have and how happy they are likely to be over time. By that standard, the people at the top of their game are doing much better because they find their jobs more interesting. They are still stressed, but differently: they wish they had more time "to feed the LLM at night," which is not the same as wondering whether their team can get through the organization's decision-making malaise. On average, though, the industry is under stress. Even people who are doing well worry about falling behind or becoming "roadkill" as the industry changes.
A meetup that sounded like a foreign language
To show how fast things are moving, Singhal describes a recent meetup of his head-of-product group in San Francisco. Many members were building tools for their companies or for their own productivity, so the group held a show-and-tell. Presenters came from a startup, mid-size companies, and late-stage companies.
Two things stood out to him. The first was the joy in the room. People had their laptops open and were one-upping each other, describing what their "chief of staff" apps did for them. The second was that the way they described product decisions, prioritization, and information flow inside their companies looked like a "completely foreign animal" compared with how he had worked only a few years earlier. He told the room that none of it, including agents in the enterprise, chief-of-staff apps, spending all their time on judgment, and writing software around anything that could be made obsolete, had even been in the vocabulary 12 months before. So what would it look like 12 months from now? According to him, the room went quiet. Nobody could have predicted that conversation a year earlier, and nobody could say where it was going.
Judgment becomes the job
He still offers a prediction for the next two years. Product leaders will increasingly be paid to exercise judgment and to be "the tip of the spear" in making everything else obsolete through software, AI, and agents. Part of the excitement, he admits, is that most of what PMs never liked doing is exactly what AI is going after. He expects most companies to have automated the mechanical parts of building product within two years. Because testing and changing things will become so much cheaper, products may see "10 to 100 times more" changes than before, which makes judgment "pretty much paramount."
When Lenny asks what judgment means, Singhal describes it as evaluating whether a change is good or bad, and whether the product should change one way or another. You cannot build 100 custom versions of the same product without damaging the brand and maintainability. Judgment means deciding how to build something sustainable and differentiated, and whether a change meets that bar and is worth building and releasing. He calls it "the system skill" that has existed since the early internet: the focus is not on the feature but on the system or platform being put together.
"There won't be any more bad software"
As an aside, Singhal predicts that in two years there will be no more bad software, while admitting this may be "more of a wish and a dream than a prediction." His house has about 15 apps controlling everything from the shades to the air conditioning to the garage door, and almost none of them work well or are ever maintained. He expects that someone will "tell Claude to fix it" and it will get fixed, and be more secure too. Once that happens, he argues, people will tolerate bad software much less. He imagines a "super skill" run against every app in the app store that turns out more consistent, less buggy, more maintainable versions.
Lenny adds that his most common prompt to Codex and Claude is simply to ask how the product experience could be better, then tell it to implement the first seven suggestions. He also notes that many such apps were built by companies that aren't product-first and didn't care much about the software. Those companies now have access to highly skilled AI engineers, and all it takes to ask for better software is English.
Singhal pushes the point to legacy systems. He says that until very recently there may have been more lines of COBOL than of any other language, and that mainframe sales remain a large line item for companies like IBM. He once spent an hour and a half trying to get his United MileagePlus account to work with his daughter's phone, which he attributes partly to complex mainframe-based systems. Many of the engineers who wrote that code decades ago have, in his words, literally passed away, and touching that code is "all downside," so nobody does. He is excited that AI could change this.
Shed 30,000, rehire 8,000
Singhal's most striking prediction is about staffing. Companies are looking hard at headcount and asking whether they over-hired. Many public companies roughly doubled their staff over the last five years, and they are now asking whether they got twice as much for it. He recalls that at Google, more than 10 to 15 years ago, people on ancillary teams like his used to ask how many employees Google really needed to hit its numbers. With 20,000 to 40,000 people at the time, he suggests the honest answer was closer to 9% than 90%, maybe about 500 people to keep the lights on and build the business. Companies hire beyond that because they want to expand and try new things, not simply because they want bureaucrats.
Now, he says, "a judgment day has come back." Companies feel they didn't get enough from recent hiring, and AI requires a different skill set. Together, he predicts, this will mean that "in the next 12 to 24 months, we're going to see massive shedding of staffs, and then massive rehiring." A company might shed 30,000 people and hire 8,000, and those 8,000 "are going to all be AI-first." He calls this "dark" and expects it to make the coming year or two very difficult.
The most open PM roles in years, and the builder divide
Lenny offers a counterpoint from his recent job-market report: open PM roles at tech companies globally are at their highest level in more than three years, last seen around COVID. Singhal says the report lined up with three points he had planned to make: builders are going to have the time of their lives, compensation is up, and the Bay Area is back in favor.
How can there be record openings while so many product people struggle to find roles? Singhal says it depends on how you define a product manager, and that the definition has, for the first time, shifted dramatically. Three years ago they discussed various PM archetypes, some more in demand than others. Now, he says, "the information mover is essentially going to become a dinosaur." He estimates that about half of product people who grew up in the industry have information-moving as their core skill. The other half came into product because they like to build, and those are the people everyone wants. Engineers, designers, and marketers can be builders too, and he expects "builders wanted" to be the tagline for the next couple of years.
He ties this back to satisfaction. As a PM, he used to take breaks to change light bulbs at home, because seeing something broken get fixed was so rare in a product job. That rarity is part of having responsibility without authority. Now PMs can create a design themselves instead of persuading a designer or waiting in a backlog.
He also sees builders moving into other functions. In his community's first two to three years, while it grew to 60 or 70 members, there was one founder. In the last 12 months, as it grew to about 125, 14 members chose to found companies instead of taking another product executive role. One very senior member interviewed for a CHRO (chief HR officer) role because the company specifically wanted a product background. Forward-leaning companies, he says, want someone who brings obsolescence, judgment, empowerment, and building skills to the function, and the function itself may be the easier part to learn. He expects the lines between product, engineering, and other roles to blur in both directions.
If you don't love building
The flip side, he says, has to be said out loud. Many people in product say things like "I'm not really into tech." They took the job because it paid well and suited their strengths in communication, moving information, and team building, things Singhal says he loves too. "But if you don't love building stuff, you're in trouble." Some of those roughly half may need to leave tech, start a non-tech business using AI tools, or find entirely different work. He describes the non-builder problem as a "mirror image" of the builder growth story.
Lenny raises a counterpoint from his conversation with Amol Avasare, head of growth at Anthropic. Because engineers can now do so much, PMs are getting squeezed by the volume of features, ideas, and documents they have to track. Avasare's view was that a PM's leverage may be higher when they are not coding and shipping, and that Anthropic needs more PMs.
Singhal says it depends on what "shipping" means. If you have 50 engineers building for customers and you become the 51st, that is "kind of a cheap knockoff of an engineer." If instead you are building ways to keep track of what those 50 people are doing, replacing tickets, backlogs, and stand-ups, that is where the leverage is. At the CPO meetup, most of what people had built was internal tooling to make their product organizations more efficient. Some companies already say they have fully automated product reviews and product stand-ups. If ten times as much is happening, judgment is needed to decide which changes are good, "and right now if it's manual, we're cooked." Companies will therefore hire product builders with judgment and, increasingly, people whose job is to build internal decision-making tools, through technology rather than more people and management layers. One CPO's reaction captures the appeal: they hated status reports, so they wrote something to replace them, and their boss is happier because they get more detail.
Adults, pace, and a diversity setback
Singhal adds several more predictions. "Adults are still going to be needed." Fast-growing companies are often led by classic founders, and while AI supplements a lot, judgment comes from expertise combined with wisdom. Members of his community tell him they appeal to companies because they have wisdom but stay hands-on: they can talk to founders in their language and have "seen the movie."
He expects pace to keep increasing, partly to "feed the beast" of LLMs running overnight and partly because the opportunity to move faster is so large. He is not looking forward to what that will mean for burnout.
He also offers what he calls a personal worry: that geographic diversity and diversity in general are going to take a step back. As the industry grew, it made an effort to bring in people from different backgrounds and locations. But the AI wave is so centered on the Bay Area, and companies are hiring fewer people, so they tend to hire people who "look and act like themselves." He believes age, gender, and ethnic diversity are all taking a hit, possibly setting the industry back "quite a number of years." He doesn't think anyone is doing this on purpose. But when pace is this high, people in their power years who are having children, he mentions women in particular, don't have time to spend nights and weekends in Claude Code. He says the industry doesn't talk about this, "but it's absolutely true."
Brands matter less than being modern
One of the most surprising shifts, Singhal says, is that personal brands, meaning the companies on your résumé and the products you shipped at scale, matter less than how modern you are in delivering product. In their last conversation, he and Lenny had emphasized the value of those brands. Now, if the whole way of building software is alien compared with the last decade, how you shipped things in the old way becomes less relevant. The interview feedback he hears is about scenarios: which tools you use, what your judgment is, how you think. It is not about the thinking behind something you shipped five years ago. Spending six years at an established company that isn't working in a current way can leave you feeling like you've come out into a different world.
He adds that at the biggest companies, it is hard even to explain what you did. Spending two years at Meta making part of an algorithm run a little faster may have had huge impact and required real skill navigating the organization. As a former Meta employee, he says he respects that as a promotable achievement. But it "falls very flat" in a conversation with someone "living in the future."
Lenny summarizes: the skills that used to be valued in PMs are changing substantially. Singhal goes further and says they may be "flipped upside down." Many people start as builders and are then taught to value leverage, scale, organizing, and empowering others: "stop working on the car, work on the factory." That is how the industry matured. Now it may turn out that scale can happen very differently, and what matters is your opinion and what you build. "That's very jarring."
Why reinvention is so hard
When Lenny asks for specific advice, Singhal begins with psychology. Humans aren't designed to change easily, and we are taught to change less as we age. Kids fall down constantly, reinvent how they move, and learn languages quickly because they aren't afraid of mistakes. He gives his own example of deciding he was too old to learn to ski. Adults are trained to find a stable middle ground and change as little as possible: find a partner, settle down, find a job and stay, treat changing jobs as a failure to avoid.
That creates a mental block. When told to reinvent themselves, people first ask whether it's really necessary. At a deeper level, he says, the feeling is "that just wasn't the deal": I went to school, worked hard, built the brand, became a manager, and now I have to start over? Twitter makes the new world look fun, but part of your mind just wants to go back to how things were. He thinks this block "is actually at the heart of the matter today."
Time is the next obstacle. In the power years, he says, the goal is to "equally disappoint everyone in your life." You have maybe 6, 8, or 12 hours to give and 20 hours of demand, so the only workable prioritization is to make sure no single group, whether parents, kids, health, friends, partner, work, or retirement savings, is disappointed more than the others. Adding reinvention on top of that "disappointment algorithm" is, as he puts it, "quite dark."
Two more factors make it worse. First, the target keeps moving: take a week off to catch up, and three months later what you learned is already outdated. Unlike changing jobs, where you grit your teeth and eventually get back into flow, "I'm never in flow because I got to keep doing this over and over." Second, and most surprising to him, the people who mastered the old game find reinvention hardest. He calls this a "shadow superpower": the better you are at one system, the less likely you are to recognize a new one, because your world is working. Weaker performers have nothing to lose by changing, while strong performers have no incentive, and their employers may be reinforcing that they're doing great.
His main advice is to have the courage to say that work is changing, that you need to stay modern, and to "cross that mental threshold" and prioritize it above everything else. If listeners take one thing away, he says, it should be that each of them needs to find it in themselves to cross the threshold toward embracing reinvention.
Lenny connects this to reports that the heads of the major AI labs, including Demis Hassabis, Sam Altman, and Dario Amodei, said they would slow down if everyone agreed to. Lenny's point is that game theory makes that impossible, so the change is happening regardless, and the only choice is whether to pretend otherwise or lean in.
The chaos will settle
Singhal offers what he calls a "baby version" of this story, meant to give some comfort. Product management was originally a structured discipline at hardware companies like HP, Cisco, and AMD, with long engineering cycles. Internet companies disrupted it: Google, finding that existing product management wasn't working for it, created the APM program to train a new breed from scratch. Microsoft, Meta, and others followed. For a few years this was jarring, because the new product management resembled the old one "pretty much in name only."
He thinks the next couple of years will be similar: new agents every three months, new forms of judgment, blurred roles, people entering and leaving, "it's going to be chaos." But after a few years, things will settle. Companies will be built a certain way, there will be training and consistency, and your next job will look like your last one. He stresses that he is not saying people will be on a merry-go-round that spins faster for 30 years until they "go vomit in the corner." He is saying that right now, people who love building need to stay current because they will be happier and more relevant, and people who don't love building need to recognize the industry is moving away from them. Lenny finds that empowering: this is a period to get on board, not a permanent state of sacrifice.
Finding a "moment of joy"
For people who are afraid and feel stuck, Singhal suggests a simple exercise: color each meeting in your week green, yellow, or red. He bets most PMs in traditional product organizations would see mostly yellow and red, while those moving into build mode see mostly green and yellow.
What surprised him is that people make the shift at a specific moment: the first time they feel joy using the new tools. The stories vary and are very personal. It might be an app built with a partner, a chief-of-staff app to manage an inbox, or controlling the lights at home. These stories often come with "and I stayed up all night." His wife, who is not an engineer, went from using AI to write a business plan for a business idea to actually test-marketing it. After that moment, people have "caught a bug," and they move from fear to joy. Joy, he argues, is "the biggest antidote to burnout." Once work stops feeling like work, the rest of your psyche finds time, stops feeling like it's disappointing others, and builds energy. People have more energy than they realize; they're just exhausted by the monotony of what product management had become.
Some people will find all of this boring or nauseating, and he says they should respect that and be honest with themselves that they may not be suited to the next version of the industry. But many anxious product people, he believes, will be happier once they cross over. He advises leaders to look for these moments of joy in their teams, because they are contagious. He is caught up in it himself: he picks TV shows he can vibe code alongside, such as Amazon Prime series like Cross and Jack Ryan, and once rewatched a season of 24 while coding the whole time.
Singhal's stack and the obsolescence mindset
Singhal says he has been "pretty all in" on Claude for about three months, after about a month using Codex heavily because he found its highest-reasoning modes advanced. He finds switching tools hard, so he tries to standardize.
He builds web properties for his community around anything he can "obsolete and code." With 100 members, not everyone can meet everyone, so he used to decide personally who should meet whom based on who hadn't met yet and what each person needed. Now an agent does the matching. Another agent collects the roles his heads of product are hiring for and matches them with members interested in work, which he calls "the next generation of recruiting." He also has an AI trained on his content that answers people's questions. He reviews the answers, spots recurring themes, and writes about where he and the LLMs disagree.
The principle comes from early in his career. He asked the best engineer he knew for the definition of a great engineer and expected an answer about degrees or technology stacks. Instead, the engineer quoted their father, an engineer from before the tech era: an engineer is someone who obsoletes themselves from everything they do. Singhal has carried that into every job, though he still meets people who don't want to obsolete their own work. AI, he says, has "put an eight ball on that," because now you can just ask the AI to do it. His stack is essentially whatever lets him obsolete everything he does day to day.
Lenny's recommended starting point is to solve your own problem: open Lovable, Claude Code, or Codex and describe in plain English what you want, such as a dashboard for your Sonos. Singhal initially thought this required systems-engineering skill. Watching his wife changed his mind: "You don't even need to be an engineer. You just have to be opinionated on what you want to see."
He admits the path isn't easy. Change feels like such an alarm that it's hard to hear that what's changing is the part of the job you didn't love. You have to go "through the tunnel," and the tunnel may include changing jobs. He predicts that most listeners will be in a different job within five years, either because their company struggles to stay modern or because it sheds and rehires. Since this change has been forced on everyone, he says he has a lot of empathy for people who are gun-shy about it.
Pace, ego, and thinking one move ahead
Beyond finding joy and adopting the obsolescence mindset, Singhal gives three pieces of advice. First, increase your pace. The next two years require "fire in the belly." He compares it to the first year of a new job or a new relationship after a long one, when you bring your best effort: "You got to find that reserve," even if that means disappointing others in new ways to make time.
Second, swallow your ego. He doesn't want anyone saying they will only consider roles at their previous level. If everything is changing, past brands matter less, and people should be willing, and even look for opportunities, to take smaller roles so they get through the tunnel properly.
Third, stay focused on the long term. This is the idea behind the name "The Skip": good career advice is about the move after the next one. The next few years are about getting on the boat to the new world; once there, "the cream rises to the top," and people can bring their leadership and skills with them. The goal is to protect your skip opportunity, meaning the high-paying, premier builder role.
Where product managers go next
Asked where PMs will end up, Singhal describes three things happening at once. First, he is bullish that PMs will spread into every industry as "agents of change." They can communicate, they have the broadest view of the organization through a technical lens, and ideally they are the first to adopt the tools. He imagines product organizations transforming first, then marketing and sales, private-equity-owned companies, and even schools realizing they are behind and looking for someone who "works in the future." He compares product leaders to dandelion seeds scattering. Second, he expects people to move into product from design, data science, and engineering, since anyone with judgment, communication skills, and a point of view may want to leave their lane. Designers, for example, might make the product itself their platform rather than pixels. Third, others will worry they can't get in. That these three changes are happening simultaneously, he says, explains much of the anxiety.
Lenny brings up a tweet listing the "only four jobs" that will remain: the product engineer/vibe coder/PM "slop cannon"; security, SRE, and infrastructure; "hot people" who present an easy UX to the world through sales and customer-facing work; and "grown-ups." Singhal agrees, connecting "grown-ups" to his point about adults and noting that opinionated people at the top of their field who can communicate broadly fit the "hot people" category.
On alignment, Lenny passes along Avasare's comment that more and more of his time as a PM goes to alignment. Singhal breaks alignment into parts. Much of it used to be getting people the right information, the ground truth. He describes projects where documents came to him, he edited them for his boss, and that boss edited them for their boss, with the ground truth buried and everyone adding spin. AI makes that part dramatically better: a CEO can ask an agent how something is performing or what a customer really wants. What remains is deciding and fighting for a position, which becomes clearer with less spin. "Alignment won't go away. It's just not going to have as much theatrics." He bets that about 80% of PMs, asked honestly whether they want their boss's boss's day of back-to-back meetings (not the pay or status), would say no, and he predicts that answer will change within two years.
Engineers and the design plateau
Lenny notes that engineering is changing even more than product, and suggests surviving engineers will become "more PM-y" as coding gets solved. Singhal says engineers have two advantages: they think in systems, so they can judge whether a change is sustainable, and they think more naturally about obsolescence and automation. In his view, product people have an edge in judgment and communication, engineers in systems and scaling, and designers in taste. All of these remain important, and people who have all of them will do best. The industry is "more than safe," as the hiring data shows, but it will involve "a different class of individual."
Lenny is surprised that his data shows design roles plateauing, since he expected design to matter more as products multiply and beauty becomes a differentiator. He adds that while AI can make him a much better PM, he never expects it to make him a great designer. Singhal suggests the industry may not yet know what to make of design in this era. He also proposes a split parallel to builders and information movers: "pixel generators" versus "taste makers." He worries that companies confuse design with production rather than taste, even when hiring design leaders, and that this bias is showing up in hiring plans.
Lightning round: perspiration, anxiety, and a Tesla growth idea
In the lightning round, Singhal admits he isn't much of a reader now, because vibe coding and keeping up with his agents, Reddit, and X have replaced most of his reading. He mentions Percival Everett's James, which retells The Adventures of Huckleberry Finn from Jim's point of view. He found it fascinating to revisit a book first read as a child from another angle as an adult. He recommends the TV series Paradise and Lioness, and says they pass a new bar: he doesn't code while watching them because they require his attention.
His favorite recent product is Tesla's self-driving. He says he isn't a car person. He had driven a Model S for years, and when his daughter got her license, he upgraded to a newer model and now self-drives about 95% of the time. His wife noticed during a snowy drive to the mountains that he is anxious when driving, something he hadn't realized after nearly 40 years behind the wheel, starting at 14 in Kansas. Self-driving removes that anxiety, and he tries to eliminate anything that causes anxiety at this point in his life. Lenny, also a long-time Tesla driver, says it became very good around version 14.2. Singhal points out a product challenge: many people tried earlier versions, turned them off, and are hard to win back. He suggests Tesla let owners gift friends 30 free days of self-driving, combining a referral with a trial.
His life motto, from his high school yearbook, is the quote attributed to Einstein: "Genius is 1% inspiration, 99% perspiration." To him it meant hard work matters most. Read through the lens of AI, he finds it fascinating, because AI will now do the perspiration. We are moving toward a world where inspired individuals set things in motion, he says, while still recognizing that the perspiration is necessary.
He also describes The Skip: a podcast and newsletter created because he felt there was too little content from operators sharing practices with newer operators. The community has grown from about 20 or 30 members at his first appearance to more than 125, and he keeps growth slow to maintain trust. A new project, skip.help, offers agents trained on about 50 community leaders, so a question about interview prep, navigating a workplace, or building a chief-of-staff app gets answers from many of them, not just Singhal.
Smiling exhaustion
In his closing advice, Singhal says there is a lot of room for optimism, but getting there requires a short period of change and exhaustion. Once people reach their moment of joy, it's infectious. The longer they wait, the harder it is to cross over. He acknowledges it takes considerable "activation energy," and notes there is some safety in numbers because so many people are going through it together. He urges everyone to "try their hand at rethinking their craft."
When Lenny asks whether he really sees people in his community thriving, Singhal describes it as "smiling exhaustion." Before, it was just exhaustion, and he would take smiling exhaustion over that. But he doesn't pretend the difficulty will go away soon: "the pace is relentless," and there is nothing he can say to sugarcoat that.
The skills that used to be really valued in product managers are changing substantially.
It's going to be chaos. Our industry is very much in stress. Nothing's constant. Everyone's in a state of alert. If you talk to product leaders 3 years ago, their day was largely moving information. The information mover is essentially going to become a dinosaur.
I just did this report on the job market. Interestingly, we have the most open PM roles globally in 3 plus years.
This is a complete renaissance for the product industry, but it comes with a lot of strings attached. In the next 12 to 24 months, we're going to see massive shedding of staffs, and then massive rehiring. You might see a company shed 30,000 and hire 8,000, but the 8,000 people are going to all be AI-first. The builders are going to have the time of their lives, but if you don't love building stuff, you're in trouble.
What are some things that people should do to thrive in this future that is emerging?
You have to find ability to increase pace. You got to find that reserve. The next 2 years requires a lot of fire in the belly.
Today, my guest is Nikhyl Singhal. Nikhyl is, in my opinion, right now, the number one best source of career advice for product managers and for tech people in general. He was a long-time exec at Meta and at Google, CPO at Credit Karma. He's also four-time founder, and he leads the best community out there for heads of product and chief product officers called the Skip Community. He also has a larger community for tech professionals called the Skip Coach. And through these communities and his 30 years of building consumer products at scale, and also his podcast, which I've recently partnered with, he is constantly gathering and meeting with and speaking with top product leaders around the world about what's happening and what's changing in the lives of product managers and tech workers in general. And the answer is a lot. This is an episode that every single product person needs to listen to and you won't find a more real talk and actionable overview of what is going on and where things are headed in your career and also what you should be doing about it right now. Seriously, do not miss this conversation.
Before we get into it, don't forget to check out lennysproductpass.com for an incredible set of deals available exclusively to Lenny's Newsletter subscribers. With that, I bring you Nikhyl Singhal.
Nikhyl, thank you so much for being here and welcome back to the podcast.
Yeah, thank you Lenny. I appreciate version two. And all my notes were like Lenny version two. So, I'm quite excited about being back on the show. You've done so well since the last time that I visited and appreciate the opportunity to share with you my current thinking.
Yeah, so you were actually one of the launch episodes, the first 20-30 guests that I had on the podcast. This was two or three years ago, something like that, and a lot has changed in the world of product management since then. And we're going to be basically spending this entire episode talking about what is changing in the role and the career of a product manager.
And what I especially love about you, talking to you and hearing your insights, is you don't sugarcoat what's going on. You're very real about like here's what you need to know about what is going on. So, we're going to be talking about the good and the bad and just like a lot of advice for product managers in particular.
To kick things off, give us just kind of the big picture view into what is changing for product managers, the good and then maybe the scary stuff.
Yeah, it'd be a lot shorter of an episode if we just talked about what didn't change.
Mhm. Wow.
I think that says a lot.
Maybe I'll start with this. I think that when we first had chatted, it was like in maybe the end of COVID, I think. The ZIRP era, as we called it, zero interest, you know, kind of free money from investors, was just kind of cresting. We talked about how ICs are now more in demand. We talked about how these first round of layoffs are existing, that ex-growth companies are going to be a struggle. But if you really talk to product leaders that were kind of in that mode three years ago, they weren't very happy. And what I mean by that is their day was largely a day of moving information from one to another. Let me frame the way that my team is presenting the information to my boss, so that that person can frame it to their boss's boss.
And generally the function had become extremely focused on responsibility without authority. And so that is the greatest form of workplace stress.
Now, we don't talk about that. We talk about all the stresses that we have today. Boy, AI is going to replace our function, etc., etc. But the honest truth is if you think back, if you've been in product for a handful of years, that was a tough time.
Now, people were being paid well. Layoffs were just starting. The industry was huge. It was the biggest it's ever been. There were more product managers, more CPOs than ever had existed in history.
What's changed is people are having fun again, particularly product folks, because they're able to build. They don't have to rely on as many people to have impact. There's much more of a direct connection to their ideas and their ability to test and connect their product instincts to their customers. And so in many ways this is a complete renaissance for the product industry.
For a lot of the strongest builders in the group that I'm associated with, compensation is an all-time high. They have more offers than they've ever seen. They see their next job maybe being a founder, maybe being a CEO, maybe being in another function other than product, but being in the C-level. They're feeling like there's more opportunities than ever before. So that's kind of a good.
I would say, you know, honestly it comes with a lot of strings attached. I think that it starts with just being exhausted. I've never seen an industry that's more tired than they are now. I mean I think we were tired during COVID, but for different reasons.
Now I think nothing's constant. There's, you know, once you figure out how to do your job in the past you would be fine for a decade until you became a manager, and then you would be fine until you became an executive. Now if you don't stay up in the next 3 months, they'll be like, "Oh, you're doing that thing that we stopped doing 3 months ago. We don't do that anymore. Oh, you know, PRDs? Well, you know, that's not even a pri-" You know, everything feels like everyone's in a state of alert.
And I think that in addition, now you're hearing like tens of thousands of people are being shed by larger employers that are also hiring and paying triple wages. So like that's like mind-boggling, but you know, depending on your perspective, you might be on one side or the other.
And I think that particularly a lot of the mid-career people, people that are like, let's call it in their 30s, you know, life plays this cruel trick on you where you end up having your best, most energetic years of your career, your power years of career, because you finally have figured out what you're doing. But at the same time, you may be settling down, you may have kids, your parents are aging. And you for the first time have those aches and pains in your body, you have to think about diet, you can't eat cookies every day, you have to exercise.
And so between your health, the family and friends that you hardly ever see, your parents which are now worrying because you have to build a different relationship with them, they're becoming dependent, your actual dependence with your kids, and then oh by the way, your work which is, you know, will take whatever time you have, but it also changes all the time. That generation is insanely stressed historically, and now we're like, "Hey, stay up, you know, what's the latest in Claude Code? They changed it this morning." It's dizzying. So, I think there's joy, but there's fatigue in a way that I haven't quite seen before.
Wow. What an incredible overview.
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So you talk to, I don't know, hundreds of product leaders regularly. You run these communities for CPOs and senior product leaders. I guess on balance are people doing, would you say, better than like 2, 3 years ago or is it just like, oh man, everyone's like burning out and in big trouble?
I think that how people would describe it and how I describe it is slightly different. I tend to be more around like when people are doing better, I think they have more choice and they're at long term going to be happier. From that perspective, I think people at the top of their game are doing much better. For the reasons I mentioned, they're just more interested in their jobs. I think that they're more stressed. But I think they're stressed because they wish they had more time to feed the LLM at night, which is a different form of stress than the stress that they experienced in the past, which is I don't know if my point or my team is going to get through the malaise of decisioning that exists here.
So I think that people are doing better. However, I think our industry is very much in stress. I think that on average people, even if they're doing well, they feel more stressed because they worry they're either not keeping up or they worry that this industry is going to change and essentially they'll be roadkill along that way. And so that has a lot to do with, you know, people are not generally that arrogant and they don't always believe that everything's going to work itself out, and there's a lot of evidence that things are changing, and so change is hard on humans. And so I think that there's a combination of both, but I think the best people tend to be feeling great right now.
We're going to talk about, of the people that are doing best, what are they doing differently? But before we get there, let's think about the future of where things are heading. You talked about a bunch of the things that have already changed and how different the world of product management is. What do you think will change further in the next couple years to give people a sense of where things are heading?
Yeah, I had this meetup last Thursday. And it was a fun meetup, you know, I have a group of about 125 heads of products and we tend to gather once a month in San Francisco, and during this meetup, you know, we took an approach where lots of people were building things for their own companies or on their own to help themselves with productivity, and so we said, "Hey, why don't we do a show and tell? Why don't we just have you, if you're a head of product, just show kind of things that are interesting, that are worth explaining." And so we had a startup go up and show what they're doing and then we had some mid-size companies and some late-stage companies.
And you know, there were a few things that were really palpable. One was there was so much joy in the audience that people were like, "Oh, I've been building this thing and let me show you." And everyone had their laptop and they were like one-upping each other and they're like, "My chief of staff does that. My chief of staff does this thing." So that sort of builds on my point that people are having fun being hands-on.
But the second thing is that the way they talk about how product decisions are made, the way they talked about how prioritization is determined, the way they talked about how information moves within the company, looked like a completely foreign animal from anything that I had experienced when I was working, you know, a few years back.
And I got up on stage and I said, you know, if you think about how we work right now and how you folks are all talking about, you know, using agents in your enterprise, how you're using chief of staff apps to essentially drive more productivity, how all of you are essentially spending all your time just focusing on judgment. And you're spending all your time taking anything that can be obsoleted and writing software around it. I think none of that was even in the language, even in the vernacular, 12 months ago.
So now, what is it going to look like in 12 months? And everyone kind of had a pause and they're like, yeah, it was impossible to anticipate what this conversation would look like 12 months ago. It's pretty hard to understand where things are going. But I would say, maybe I'll answer your question around where things are going in the next couple years based on kind of how I think companies are going to change and how people are going to change.
So I think on the company side, and then maybe I'll slant it more towards product for a second, product leaders will increasingly get paid and be asked to drive judgment and then be the tip of the spear on trying to essentially obsolete everything else through software, through AI, through agents.
And this is partly why there's a lot of excitement. Because just to be very honest with you, and you were a PM and I was a PM, most of the stuff that you didn't like doing are the things that AI is really taking a real crack at.
And so, I think that's super interesting. I think that there's a ton of that change that's going to happen. Some companies are doing it now, some companies will do it, but within 2 years, I think, most of these companies will obsolete all the mechanical parts of building product. I think that there will be 10 to 100 times more changes that will be presented to products than ever before. Because now the cost of testing something, the cost of changing is going to be much, much lower. And so, when things are changing that rapidly, that judgment piece becomes pretty much paramount.
Just to make sure we understand, when you say judgment, what should people be thinking of when you talk about judgment?
I think that it's sort of evaluating whether the thing that we're changing is a good or bad thing.
Mhm.
I think that it's also evaluating whether, you know, we should change the product in one way versus another. You can't build 100 custom versions of the same product. It affects your brand, it affects the maintainability, etc. So, when customers are asking for things, when you're trying to think through how do you build something that's sustainable, differentiated? That's judgment.
And evaluating whether it's successfully met that criteria, whether it's worth building and worth releasing. It's almost like the system skill that's existed from the beginning of the internet. It's, you know, hey, it's not about the feature, it's around the system that we're putting together, the platform, if you will, that's, you know, kind of enabling capability, right? So, that's the judgment of, boy, there's all these changes coming in, and they're going to happen more frequently. You know, as an aside, because of all
These changes, I think that in 2 years, I think there won't be any more bad software. I mean, this is maybe more of a wish and a dream than a prediction, but I think that if you count in your given week how much bad software you come back with, right? You know, I have a house and it has like 15 different apps that run to control everything from the shades to the air conditioner to the, you know, garage door. And almost every one of those apps are flawed. They don't work particularly well. They never get monitored. Things break, you know, no one ever checks it.
Like all that stuff's going to get fixed. Because someone's going to basically sit down and tell Claude to fix it and it's just going to fix it. And it's going to fix it. It's going to be more secure, etc. So I think that that's changing and so people will have a lot less tolerance for bad software.
Along those lines, just real quick, in a quick aside to your aside, the prompt I constantly find myself using with Codex and Claude is just, how can we make the product experience better? How can we make this better? And you just ask that and it's like, here's 10 ways we can make it better. And so you're like, "Wow, these are really good ideas." And then, cool, do it. Do the first seven.
Exactly. There's going to be like some super skill that's going to run against every piece of software that's in the app store and it's going to basically go in and it's going to fix them all. And then they're going to get released and they're going to be like, "Oh, that this sucks. It's just a significantly more consistent, better, less buggy experience and more maintainable." And so that's why there's a lot of optimism, right? Because these changes can be done pretty automatically.
Yeah, just to kind of finish that loop real quick. So many of these apps are built by engineers that are not the best engineers. They're engineers that, you know, companies hire that don't really care about their software. They're just like, this is just a side thing, building this thing that we have, just an app. We just need to build an app. Let's find someone to build it. They're not product-first companies. And now all of these companies have access to the most skilled software engineer, Claude Code, Codex and all these other tools. So I totally see what you're saying. Everyone has the best engineers available now. And it's just English to ask them to build the better thing or build a better app. So that's a really interesting point.
It still boggles my mind. You know, everyone's like, "Oh, what's the cutting edge?" and all that. I mean, I don't know if this is true even today, but very recently there were more lines of COBOL than I think any other language out there. And mainframe sales continue to do pretty well and they're an unusually large line item for companies like IBM.
And part of the reason why these systems, like, you know, I think I spent an hour and a half trying to get my MileagePlus account on United to work correctly with my daughter's phone and all this other stuff. Partly because these systems are so complicated, but they're built in mainframes, right? And a lot of the engineers, and this is going to sound kind of morbid, but you know, I think it's true, a lot of engineers are dead. Like they literally have passed away. They were written, you know, 10, 20 years ago. And going in and touching that code is, you know, probably the last thing anyone wants to do. So nobody goes in there, you know. It's all downside. Now, we can change that. So I'm very excited about what it means to go in and improve things that people take for granted, right? That's a big one. That's a bit of an aside.
I think that the other thing that I think is worth kind of signaling is I think that the skills that you need to be effective in today's world is an acceleration of what we were talking about last episode. We were talking about ICs, we were talking about hands-on, we were talking about opinion even back then, before, you know, Claude and ChatGPT and others kind of came out.
I think what we're now seeing is companies are looking very, very carefully at their staffing. And they're asking themselves, one, do we need this many people? Did we over hire? And part of the reason is they're looking, hey, maybe we doubled our staff in the last 5 years. Lots of companies that are public have done that. Did we get twice as much for them?
You know, it was funny when I was at Google, over 10, 15 years ago, we used to ask ourselves, you know, I was on an ancillary team, I wasn't in the search or the ads team, we used to ask ourselves, how many people are really needed for Google to hit their numbers? And you know, there were back at the time 20, 30, 40,000 people. And, you know, if you ask someone who wasn't in tech, they're like, ah, probably like 90% of those folks, obviously. And you know, the answer's probably closer to like 9%. You know, probably you need like 500 people to keep the lights on and to build that business. You don't need 25, 30, 40,000 people.
So, there's a huge amount of overhead where companies hire not just because they want to, you know, have bureaucrats, because they want to expand. They want to try new things. But I think that there's a judgment day that's come back, where companies are like, look, we aren't getting as much for the staff that we grew in the last 5 years, and this AI thing requires a totally different skill set.
The combination is going to mean this year, I predict, in the next 12 to 24 months, we're going to see massive shedding of staffs, and then massive re-hiring. You might see a company shed 30,000 and hire 8,000. But the 8,000 people they're going to hire are going to all be AI-first. And the 30,000 they're going to let go of are going to be a combination of, we didn't get as much for those folks that we needed, and we want to set the destination differently with a much lighter payload. And that's dark. That's going to make this year and the next two years, you know, pretty challenging. So, I'll transition a little bit to my thoughts on people, but I'll pause for a second to see if this resonates with you.
That's scary to hear. We're going to talk about what folks listening can do to do their best to be in that second bucket of being rehired and kept, because there's a lot you can do, and there's a lot of people that know they need to change and adjust and they're not doing anything, and we want to talk about maybe some of the blockers there.
One thing I'll note, I should have mentioned this earlier, I just did this report on the job market, and interestingly, as of today at least, we have the most open PM roles globally at tech companies in three-plus years. The last time it was this high was kind of during COVID, basically. So, there's some good news there, at least for the PM role. I don't know.
Did that surprise you, Lenny?
Yeah, it did, because there's always the sense that, you know, why do we need PMs? What's the point? We have AI, just build stuff. And my sense, I've always been saying this, I feel like the PM skill is the most important, valuable skill of all the skills. And I know every role thinks this about their role. It's like, no, design, we need design more than anything now. But I feel like what you said, where it's deciding what to build, deciding if this is good and great and ready, and prioritizing, I feel like that's what remains. So to me it makes sense.
Your report came out for two of this time because it was right before I was preparing to come on the show, and the three points I was going to make are, you know, builders are going to have the time of their lives, comp's actually up, and the Bay Area is, you know, essentially back in favor. And I think those three things came very much loud and clear in your report.
And I think the question around, hey, why are product managers doing so well? Why are there so many jobs, when in reality a lot of product people that all of us know are struggling to find a role, or we're hearing about these layoffs? I think it depends on how you define what a product manager is, and I think that for the first time we did have a dramatic shift in what's defined. Three years ago we talked about, hey, product managers, there's lots of archetypes. Some archetypes are actually more in favor. This was the IC conversation, the builder conversation. Now what we're essentially saying is the information mover is essentially going to become a dinosaur.
And I think about half of the product people that grew into the industry, you know, have that skill and superpower. And then there were a set of people who got into product because they like to build stuff. You know, folks like yourself who were founders, that was sort of the motivation in joining the industry, and then they found themselves in this thing called product management. Those ones are builders. And those people are the ones that are being hired by your Surbhi Parekh. I mean those product managers, everybody wants a builder.
And I think that interestingly, lots of engineers are builders, lots of designers are builders, lots of marketing folks are builders. And I think "builders wanted" is going to be the big tagline for the next couple of years. And it is so fun to build. I'll bet you, and this is a prediction, that if you had to choose between preparing a podcast and sitting in Codex or sitting in Claude Code and working on your laptop, you would prefer the latter.
It is so fun. Yeah, just the progress. It's just so much fun. It's like, look at this thing go. It's getting better. It's getting better.
When I was a PM, I used to take a break and go change the light bulbs in the house. And the reason why I would change the light bulbs is that light bulb was broken, but then I replaced it and the light came on, and man, was that satisfying. Because in a product job, there are very few days of satisfaction. Because you don't really have the ability to see something broken that gets fixed. It's just part of the challenge in having responsibility without authority. Until now.
Now, you can participate in the joy. You can create a design. You don't have to wait for the designer and convince the designer to go and actually work through this, or to put your stuff on a backlog. You don't have to do that. And so I think that the builders are going to have the time of their lives. And I think they're going to be very focused on judgment. I think that they're going to invade other functions.
I think there's going to be, you know, when I started the group 5 years ago, we had for the first two to three years, until we got to about 60 to 70 people in this community of heads of product, we had one founder. In the last 12 months, as we've gone to about 125, we have 14 founders. 14 people essentially have decided that their next job was not to take another product executive role, but to found. Founding CEO is now open to us.
I have one very senior person in my group who interviewed for a CHRO position, because they wanted a product manager background for the CHRO position.
CHRO? What is CHRO?
That's the chief HR person in the company. Right? So, you would never think that an HR person would be a former product manager. But now, forward-leaning companies are starting to say, "Hey, we need someone who can bring this obsolescence skill, this judgment skill, this empowerment skill, this builder skill to the function." In fact, the function might be easier to learn than the other parts of the job.
And, you know, we're seeing that trend that product builders are going to have both a broader range of opportunities up and down the stack, and it won't be just product managers, and engineers can become product leaders and product builders, and all of this blurring of the lines is going to take place.
I think that, unfortunately, the flip side has to be mentioned. I think that non-builders, and I think that anyone who sort of sees themselves as not loving sitting down and building something, there may be reasons why, we'll get into why you may not be in a position to find the time, let's say. But if you're not a builder, if you're like, "Look, my skill was never to be, I'm not really into tech." People say this all the time. "Oh, I'm not really into tech. I just really found it to be a lucrative job. It's a role where my ability to communicate, my ability to move information was, you know, where I ended up enjoying it. I love team building." You know, those kinds of nerds, which by the way, I love all those things. But if you don't love building stuff, you're in trouble.
And I mentioned about half the people are in that camp. So, we're going to have that challenge where they're going to have to perhaps leave the tech industry. It might be that they want to go build a new business outside of tech but use some of these AI tools, or maybe they want to find a job completely foreign to tech. But I think that this non-builder piece is a mirror image of the builder growth story that we're seeing.
There's so many directions we can go here. One thing I want to throw out, it's kind of a hot take, and this came from a chat I just had with Amol, the head of growth at Anthropic. So, he's head of growth, he's a PM, and he had this really interesting point that as engineers can do so much more, PMs are getting squeezed because they have to stay on top of so many things, so many features, so many ideas, so many docs, so many things being said to them. And there's this push for PMs at companies to ship yards, build stuff themselves.
And what we took away from that chat is the leverage that PMs often have is a lot higher not spending time coding and shipping, but instead just staying on top of all this stuff. And he's like, "We need more PMs now. There's so much for PMs to do because engineers are so fast. So, there's still need for prototyping to explore ideas and ideate and get feedback and align." But he had an interesting take that, "It's better I don't spend time shipping stuff. It's better I do higher leverage work as a PM."
It depends what he means by shipping stuff, because I think that if you have an engineering team of 50 people building things for your customers, and you're like, "Hey, I want to be the 51st, because that's how I get leverage," I'm like, "Yeah, it's kind of a cheap knockoff of an engineer." If, on the other hand, the thing that you're building is ways to stay on top of what the 50 people are doing, when in the past that was building tickets and backlogs and all of the things that we used to do to figure out organizations, manage stand-ups, you know, that's the information overload that's happening.
What we saw when the CPOs got together is all of the things they're building are ways to drive efficiency out of their product organizations. They're inside-the-building kind of development efforts. And I'm not sure that for the next five years we'll continue to build software that way. But I think in the next two years people are going to change the product operating system that they're working on. And we're already seeing companies that stand up and they say, "Hey, we've fully automated the way we do product reviews. We've fully automated the way we do product stand-up."
So, to his point, look, if there's 10 times the amount of stuff happening, we need judgment to determine whether these are good or bad changes. And right now if it's manual, we're cooked. So, it's a combination of hiring good product builders with judgment and then hiring increasingly folks whose entire job is to kind of build the internal tools necessary to improve the decisioning, but it's not through hiring of humans and building management ethos,
which is what it used to be in Reserve. It's actually through technology, but it's a totally different way of building software. And that's what gets people excited cuz they're like, "Wow, if I do this, I don't have to ever do a status report." I mean, that was a comment that was made. "I hate doing status reports." So, now I just wrote something and my boss is happier cuz they get more detail. And that to me is incredibly exciting, but it is a different direction of what you're trying to deliver than something that goes out the door.
That is such a good distinction and makes all the sense. Basically, it's make yourself scale through software as much as possible. There's a big opportunity and it's fun. It's like you're building your own thing.
That's right. That's right. I think a few other things that I would just note around how things are going to change in next couple years. I think that adults are still going to be needed. I think companies are going to grow. They're going to grow quickly. I think those that are driving some of these initiatives are classic founders. And AI is great at supplementing a lot of things, but I think judgment comes in the form of a combination of expertise and wisdom.
And so I think that increasingly I hear from my groups that hey, I'm attractive to this company because I have wisdom, but I stay hands-on. I have credibility with the founder, so I can have a conversation with that individual in his or her language, but I have weight to my thinking. I have seen the movie. I have experience that actually would help them as they take this turn. So adults are still going to be important.
I think pace will continue to go up partly because people will want to feed the beast, the sort of LLMs that are running at night. And I think partly because there's just such an opportunity to keep moving so much faster. And I think that's going to be dizzying and I'm not excited about what that causes for burnout.
Sadly, I think that geography and actually diversity is going to take a step back. I think that we were very good about driving more breadth as we grew the industry, we started looking at people who were from different backgrounds to populate it including different locations. But I think that because the AI wave is so heavily, you know, coming from the Bay Area and because companies are hiring fewer folks, they're hiring people that look and act like themselves. So age, gender, I think, you know, ethnic backgrounds, all of those are taking a hit. And I think that we will have stepped back quite a number of years in the diversity of what we do. And so I worry, I mean this is my personal worry, but I worry about that probably more now than I did in the last 5 years, because I think it's an underbelly of what we're seeing. And I don't think that anyone's intentionally doing anything, but I think when pace is so high, the fact is that, you know, women are having kids in those power years and they just don't have the time to spend their nights and weekends in Claude Code. And so that's an impact. And you know, we don't talk about it as an industry, but it's absolutely true.
And then the last thing I would just say, and maybe this goes into some of the advice as well, is I think that one of the most surprising shifts we're seeing is, you know, your brands don't matter as much as how modern you are in your ability to deliver product. In the past, I think for the last 10 years, it's like have you seen the movie before? And I remember even in this last podcast episode we did, Lenny, we talked about, "Hey, brands matter. You really need to make sure
Like personal brands.
Yeah, personal brands. Hey, I've worked for this company. They've delivered products. They've been at scale. So then people are like, "Oh, that person certainly knows what they're doing, right?" And you know, it's like, "Well, tell me about all the different experiences you've had." But now if every way of building software and how we deliver product is completely alien to how it was in the last, you know, 10 years, how you deliver it in that sort of version one is going to be less and less relevant.
So lots and lots of feedback that I'm hearing from interviews is like put you in a scenario, what tools do you use, what's your judgment, and how do you think? It's not about 5 years ago and you shipped this thing, what was your thinking that went into it.
And so, how modern you are now becomes the career advice, not did you pick up the established brands, cuz what if the established brands is very much working in a way that's not current. You work there for 6 years, come out and it feels like you're in a totally different world, right? So, that's why I think the next 2 years and these changes are so profound and frankly confusing to people.
That is such an interesting insight that the logo, like it used to be fancy to have all these logos on your resume, and now you're saying sometimes that may hurt you because that company's not seen as a very AI forward company, and second of all, people are looking for just like what have you actually done? You're actually aware what's going on.
Well, I was just going to say some of those biggest brands, it's hard to even talk about what you've done. You know, it's like, you know, if you're working in Meta and you spent 2 years and I managed to make this, you know, piece of this algorithm, you know, go a little faster and by the way it had a huge impact and, you know, frankly it was incredibly hard to navigate the hallways and to make that decision and to find incrementality. I mean, as someone who has worked there, I understand and respect that and that is a promotable, you know, achievement. But it just falls very flat on a conversation where someone's like living in the future and product is now totally different, right? So, that distinction is the thing that I want to just call out that, hey, that's happening every day right now.
So, what you're saying there, and which is a really powerful point, is that the skills that used to be really valued in product managers are changing pretty substantially.
Yeah, and in fact, maybe almost flipped upside down in terms of importance. You know, in some ways we start our careers as builders, many of us, and then we get taught that leverage, scale, organizing, streamline, empowering, enabling, don't do the build yourself, get others to do it. Stop working on the car, work on the factory, right? That is the maturation of our industry. And then you find out that well, what if it turns out the scale can be done very differently and all we care about is your opinion and what you build. That's very jarring and that's what we're living through right now.
So, let's follow this thread of specific advice to PMs right now, whether they're mid-career, senior, getting started. What are some specific things that you think people should do to do well in this emerging future?
Change is really hard for us. And I think as humans we're not really designed to change very easily. Like if you think about it, you know, I was thinking, you know, about why is it hard for us to change when in some ways change can lead us to much better outcomes. You know, we're almost like told to change less as we grow older. You know, when you're a kid you fall down a ton, but like when was the last time you fell down?
Not often, except my son loves to pretend like we're falling. So, there's a lot of pretend fall.
And when you pretend fall, it's probably pretty jarring. It's probably relatively new.
Yeah, for him it's so fun. He loves it, but yeah, for me it's such a long ways down.
Yeah, and I think that it's funny cuz you watch kids and it's like normal for them to reinvent everything they do. Oh, I'm learning to crawl. Oh, now there's this walking thing. Yeah, crawling is not for me. You know, it's why kids learn languages so quickly because they are not afraid to make mistakes and they go through things much more rapidly. It's why you teach your kids to learn how to ski early because boy, you know, I just made a decision. Hey, I've never been a skier and I'm just like too old to do it.
I think that we are trained to find a happy medium and then make as few changes as possible. Find a partner, get settled down. You know, you find a job, try to stay. It's a failure to transition to a new job if you can avoid it. You know, that's our entire model and so we create also in some ways a mental block around this idea of reinventing oneself. You know, when you are told to reinvent, when you are told to change, the first thing you think about is, is it really necessary? Boy, it seems exhausting. I worked so hard to get here. Why would I need to?
And I think in the most inner psyche of some of us, it's that just wasn't the deal. The deal was I did what I was supposed to, went to school, I worked hard, I got a job, I built the brand, I got to be a manager, I'm making the income, I have the, you know, whatever it might be, the partner, the family, you know, all the stuff. You're telling me after all this time I got to start over? Like, it sounds fun. You read Twitter and you're like, wow, all these people are doing all this crazy stuff. Then the back of your mind is like, I just don't know why. Why did we get here? I don't want to do it. I want to go back to the world where I can just keep doing things. I think that this block is actually at the heart of the matter today. And it's a skill, reinvention. And it requires time.
But time is so hard to find your power years. You know, for the reasons we mentioned with so many, you know, your goal when you're in your power years is to equally disappoint everyone in your life. Which sounds like a horrible statement, but it's true. You have 6 hours to give, 8 hours to give, 12 hours to give, and you have 20 hours of demand. What is your prioritization mechanism? I am going to equally disappoint everyone. Not disappoint one group. My parents will not be more disappointed than my kids, than my health, than my family, than my friends, than my partner, than my work, than, you know, my retirement account. Like that's essentially what my mindset is. It's I need to equally disappoint everyone. Now you're telling me that the number one thing is to reinvent when I'm barely able to manage this disappointment algorithm. It's quite dark.
But, I think that, you know, there's this setup. And then the worst part is these two. One is, "Okay, fine. I'll take a week off and I'll go figure out what people are doing and what the latest is." And then it turns out 3 months later that week off is now antiquated. You got to keep doing it because the target keeps changing. It's not like I went from not having a job to having a new job, and then I kind of grinned and bear it and got through it, and now I'm back in flow. It's like I'm never in flow because I got to keep doing this over and over and over again.
And the most surprising observation I made is that the ones that were the best at working in the past, the ones that mastered the old game, find it the hardest to go through this reinvention stage. It's this sort of shadow superpower thing that I talk about. You know, the better you are at mastering one system, the less likely you are to sort of recognize the new one because your entire world is like this is working for me. And so, the weaker you are, the more excited you are about changing. Hey, what I'm doing isn't working. Might as well change it. But, if you're really good, you have no incentive to change. And perhaps even your employer sees you doing great, and the company itself is in this moment. So, all of these things, whether it's the shadow, whether it's the exhaustion, whether it's the time, whether it's the fact that the target's moving, creates this reluctance to reinvent.
But, the number one piece of advice to answer your question is you have to have the courage. You have to believe. You have to have the power to essentially say, "Look, I know the way we work is changing, and I need to stay modern. I need to stay current. So, I am going to cross that mental threshold. And I'm going to prioritize that above all else." That crossing the threshold is the key. And I'll talk a little bit about how one does that, but I think that, I mean, if there was one thing to get away from today's discussion, it's every person listening to this podcast needs to find it in themselves to cross the threshold around embracing reinvention. That is the world that we live in now.
Damn, Nick. This hits hard. I told people you don't sugarcoat stuff, and this is what we're experiencing now.
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What I think about as you talk about this is, I don't know if you saw this, they asked all the heads of the AI labs, like Demis and Sam Altman and Dario, just like, okay, if everybody agreed to slow down and stop this stuff, would you do it? And they all said, yep. Which says a lot about just like they're all like freaked out a bit about how fast everything's going, how much is changing. And then there's the reality of, but that is not going to happen because the game theory of it all is it doesn't work. You can't slow down cuz no one will actually slow down. Whoever doesn't has a huge advantage. And so I think it's just a big part of this insight is just like this is happening. And there's nothing you can do to slow it down or stop it. And you can either try to pretend like it's no big deal and it's going to be all right, or you can, as you said, get over this hump of just like, okay, I need to lean into this and see what I can do.
Well, and maybe there's a baby version of this that perhaps provides a bit more kind of solace and optimism. A baby version of this is that, you know, the way that people did, let's call it product management, back in the day when HP and Cisco and AMD and these other companies built products that were, you know, physical hardware, they had long engineering cycles. There is a discipline called product management that was birthed. And that discipline had a very, very specific, very structured way of working that was essentially imploded when the internet companies came along and Google for one built the APM program because they felt like, "Hey, this product thing that exists in the market isn't really what we need. And we're not seeing success. And in fact, we're going to just train from the beginning this new breed." And, you know, that then birthed a lot of the current product managers; Microsoft and Meta and other big employers started to kind of create a new version.
And for the first few years, it was very jarring because everything that they did that they call product management resembled old product management pretty much in name only. And there wasn't like you go to business school, you know, you get a business school degree and all of a sudden you're a product manager. You would have to work, you have to build some expertise, then you'd have to come
in and help organize and collaborate and all this other good stuff. The next couple of years are going to be like that where, you know, every 3 months we're going to have more agents, different forms of judgment, they're blurring the lines on what the role and responsibility. People from different backgrounds coming in, people leaving the... it's going to be chaos.
But as a couple of years go by, things will settle. Companies will be built a certain way and it won't be that you'll continue to change the way you're working. You'll have reached some form of optimization. We're just not in that optimization in any way, shape, or form right now.
And so, the speed of iteration and how you think about, well, look, my job is not to move information. My job is to evaluate. I know I have to think through what does success look like, whether this makes sense for the system. It's a totally different skill. But after a couple of years, there's going to be some routineness to it. There's going to be some training. There's going to be consistency. The job you had next is going to look like the previous job. A lot of this is...
So, all I'm making a point is that you need to cross the threshold to stay modern because things are changing. But I don't want to send the point that for the next 30 years, you're going to be on this merry-go-round that's going to spin faster and faster and faster. And then you're just going to have to run off the merry-go-round and go vomit in the corner. That's not at all what I'm suggesting. I'm just saying that right now is the moment when if you love building, you have to stay current because you will be happier and you will be more relevant. And if you don't love building, you have to recognize the industry's moving away from you. That is the key point. And I don't think there's a person that's looking at the current way of building product. I don't think there's a person who's been on this podcast that would disagree with that statement.
That is a really empowering point to make there, that this is not forever, that it's a couple years potentially, maybe, I don't know, could be a little bit longer, but it's not a forever thing where you have to do this. You have to lock in and sacrifice forever. This is the moment to get on the rocket, to get on the ship. I don't know. It's a nanobot. The boat. Whatever metaphor you want to use.
Whatever transportation.
So, I think that would make me feel better. I think the other, like, I don't know, the good, again, just to remind people like this, you know, it sucks to have to change. The good, as you shared earlier, comp has never been higher. There's a lot of open roles. People that are embracing this are having a lot of fun. Like most PMs are sitting there all day waiting for stuff to happen, waiting for meetings and approvals, and all this lying in and all this PR reviews. And now it's like you can ship stuff so often. There's so much good that is happening. Maybe just remind us again of anything else there, just to inspire people to like, okay, this is worth it.
Let's go to the individual you're describing. There's someone who's sitting, who's really afraid, who's a builder, who's like, "Man, my job is changing so rapidly and I'm so nervous and I have to think through what's my career going to look like." But I tend to ask the question like, "Do you really love your day?" Like if you put green, yellow, and red next to the meetings you had and did that for a week and then we looked at the color chart, I'll bet you the vast majority of PMs that are in a product organization, they show mostly yellow and red. And I'm telling you, the ones that are moving into more of this build mode, it's mostly green and yellow. And yet most of them are sitting very, very afraid, feeling stuck.
So what I'm suggesting is how do you then transition mentally and then physically into a moment of going from this moment of fear and being on the sidelines to being in the day. What I have noticed, and this is sort of a big kind of surprise to me, is there's a moment where they experience the first joy in using the new tools. Everyone has a story and it's always different, but it's super personal. It's going to be like, "Oh, I was doing it a certain way and then all of a sudden I built this thing." And oftentimes it's like my partner and I used this app that I built, or I built a chief of staff app to keep track of my inbox. Or I manage, you know, the lights in my house using this thing. And it's some silly thing.
And usually it accompanies with a story like, and I stayed up all night. Or I spent a bunch of time talking to my friends, or hacking away, or I just spent time talking to Claude about it. You know, even my wife has a story about how she has this business that she's thinking through and she went from using the AIs to, you know, do the business plan, to actually do test market. And everyone has this moment of joy and then they're like, "Oh," it's like they've caught a bug. And at that moment is when they cross the threshold between fear to joy.
And joy is the biggest antidote to burnout and it creates opportunity because the moment you have joy, the moment it doesn't feel like work. And I think most product management feels like work if you're not building. And we are now moving into a world where product management will be building and joy, not work. So, you just need to find a path to get there. And the moment you do, the rest of your human psyche creates time, doesn't feel like you're disappointing others, and builds energy. 'Cause people have more energy than they realize. They're just so exhausted by the monotony of what was defined as product management.
And so, that is the number one piece of advice: have you found joy? Now, there's a class of person who's like, "None of this is joyful. Like, I find the whole thing to be kind of boring, nauseating. I don't really like it." I'm like, "Well, then you're probably not in for the next version of our industry." You know, and you should be respectful of that and you should be honest with yourself. But there's a lot of product people that are right now very anxious that actually are going to be happier once they cross the chasm, and all they need to do is find a way to create that moment of joy, you know, whether that's an app on the side or an app at your work. And if you're a leader listening to this, you should find those moments of joy in your staff. Because that's contagious and it gets people excited, and that's what, you know, that's why I like doing what I do.
It's like I like building stuff and I caught the bug and, you know, I'm all there all the time and, you know, I try to find TV shows that I can vibe code in parallel to because, well, I want to watch TV, but I want to be vibe coding at the same time. It's like
What's a good show for vibe coding?
I think, well, a lot of Amazon Prime shows are good.
I guess not for vibe
I mean, they're built on books. You know, these books are like, they're structured and all that. So, you know, Alex Cross or, you know, Jack Ryan. You know, what's hilarious is, and you know, when you get older, you remember shows that you love, but you don't remember the plot. So, one time I just binge-watched a season of 24. The show that I loved back in the day, but frankly, I watched it and I kind of knew what was going on, but I vibe coded the whole time because it was like, hey, I'm paying attention here, but I'm staying engaged.
Well, let's actually follow this thread. What's your AI stack? What are you using to build, and what is something you built and something you vibe coded?
I've kind of been pretty all in on Claude these last 3 months. I was, for a month, pretty aggressive on Codex because I found some of their newer stuff, especially with sort of the highest level of reasoning, to be quite advanced. I find it hard to switch between tools, so I try to standardize, to be direct. Like the things that I build, I build a bunch of web properties for my community. So, you know, anytime I see something that I can obsolete and code, I try to build code around it.
So, if you had 100 people, one natural thing you want people to do is to meet each other. And, you know, 100 people can't meet 99 others. So, you have to be thoughtful around who's the best person to meet. And how do you match people up? How do you make sure that you match people with people they haven't met before? You know, what are their haves or their wants? That entire thing used to be me sitting down and thinking like, "Oh, you know, Jay-Z would really appreciate meeting Annie, but I don't know if they've met before." Now, I write software to do that. I write an agent that goes in and actually does matching. I write an agent to figure out, "Hey, what are all the jobs that my head of products are hiring? How do we make sure that we make those available, but then build a mailing list of folks who I think, when they're interested in work, get matched up automatically." So, like the next generation of recruiting.
I think a lot about using AI for content. So, when I sit down, I have an AI that takes questions from people and then it's trained on my content, like yours, and it gives answers, but then I read those questions, evaluate the answers, and I'm like, "Hey, this is a theme I'm hearing." And then I sit down and I write down, "When do the LLMs and I disagree?" I go through, and all of these things are anything that I'm doing that I think I can, you know, replicate, I try to obsolete myself.
You know, when I first started my first job, I asked the best engineer that I worked with, who still is one of the best engineers I've ever met, "What's the definition of a great engineer?" And, you know, I thought it would be like, "Oh, someone who's got this degree or is well versed in this technology stack." He's like, "Well, the best engineer I know is my dad." And of course this is before tech in that case, and he's like, and my dad's definition is still my favorite, which is an engineer is someone who obsoletes themselves from everything they do. That's the definition of a great engineer.
And I've taken that to every job that I've worked at. And it's funny because you'll run into people that are like, I don't know, I don't want to obsolete myself, that's my job. And I was like, ah, I think if I obsolete it'll be a better job for me. What AI has done is turn that, you know, it has basically put an eight ball on that. Like you can obsolete by just asking the AIs to do this for you. So why I'm saying that is my stack is what can I do to obsolete anything and everything I do on a daily basis.
That is super cool. I love hearing these stories. Like what I find is the best tactic here is just solve your own problem. Think about something that's not great in your day-to-day or something you just want to improve, and it's like, it sounds so easy. All you do is go to, I don't know, Lovable, or install Claude Code, download Codex, and just tell it, I want to build a dashboard to control my Sonos. And then it just walks you through everything you need to explore. And that's a pretty advanced thing to try, but it's just like English. Like it sounds like I have no... no how to do this. Like you just tell it, here's what I want to do, just like a person, and it helps you figure it out.
And well, I agree with you, and then I think the question is like, what skill do you have to have? Like for a while I was like, oh, that's a systems engineering skill because you need to be able to train, you know, the AIs to go after things. But then watching my wife and how she works, and she's not an engineer by any means, and she's getting tons of value. You don't even need to be an engineer. You just have to be opinionated on what you want to see.
And know what you want, yeah, know what good looks like.
And then the moment that you get it, it's when the light bulb turns on when it wasn't working before, and now you sit down and there's this moment where it's like, "Hey, I used to have to go and work to do this, but now my agents do this. And then what's the next agent I can do to make my life a little bit better?" And that's where you catch the bug.
It's such a powerful thought that your job can be much more joyful as a product manager, as any function, but, you know, we're focusing on PMs. Just like if you look at your pie chart today of how happy you are during the day, you can actually be much happier in this future. And I think that's hard for people to really realize, "Oh, wow. Okay, I can actually love this job so much more?" They did not imagine that.
Yeah, and I think that it's because you're staring at change. And I think change is such an alarm bell, it's hard to hear the voice that says, "The things that you are changing are the things you don't love." Because change is so hard for us, it's so scary, you know? And I respect that. So, I think that if your listeners are able to sort of understand that, hey, there is a world which is better, but I have to go through the tunnel, and the tunnel sucks. And the tunnel may mean that I'm going to have to change jobs.
I mean, my prediction is the vast majority of people that are listening to this will be in a different job in the next 5 years. Because they will either choose to move to something because that company will struggle to stay modern, just like we're describing. People need to stay modern, companies need to stay modern. Or their companies are going to be shedding and re-... returning off staff. And so, because change is apparent, I think it's just so deafening that people are very much gun-shy to be excited about something that's sort of forced on them. And let's be honest, it's been forced on everyone. And, you know, not something that they chose. So, that's why I have a lot of empathy, but when I talk to people, I try to dig through, forget what's happened, and, you know, how do we make the best out of it? And the best is pretty good.
So, say we've convinced a listener, okay, I need to make a change. I need to lean into this. I need to take this seriously. I can't just sit back and hope it all works out, okay? And then they maybe found a moment of joy. They built something that's super cool and just like, "Hey, check this out." What other advice do you have for folks listening to help them, I don't know, let's not say survive, but just like thrive in this future that is emerging for product people?
Thrive. I definitely think that, you know, you find that moment of joy, you have the engineering mindset, which is, "Hey, I want to obsolete myself on something that I do today." Again, reducing the little less joyful parts of my job is a good starting point.
I think that, you know, you have to find the ability to increase pace. You know, this is not a job... The next 2 years requires a lot of fire in the belly. A lot of agency, that I know everyone talks about. So, for example, if you were to leave a job and start a new job, you probably don't view the new job year one at the same pace that you, you know, viewed your year five in your last job. You need to kind of bring it. If you have a new relationship, you know, and if you've come off of a long-term relationship, my suspicion is your first year of that relationship, you put your best foot on. This is what I'm asking. You've got to find that reserve. You've got to make time. You've got to maybe disappoint others in a way that you haven't in the past in order to create time for you to stay current, find that joy, obsolete yourself from the things that are not worth it.
I think the other thing you have to do is you have to swallow your ego. You know, I don't want a single person saying, "Hey, I was an XYZ leader. I would only consider roles at that same level." I want people... This is an extension of our last conversation. It's not only is it in vogue to be hands-on,
and I see it's kind of a necessity. I need everyone to sort of say, "Look, if everything's changing, it doesn't matter what we've done in the past. That brand doesn't matter, as we discussed." You have to have an egoless perspective of how to stay current. And you would be not only willing, but actually look for ways to even take something smaller in order to make sure that you're kind of going through the tunnel correctly.
And then, ultimately, part of the way we swallow that ego is you stay long-term focused. You say, "Look, if the way we build product is changing so aggressively, my job is to spend the next couple years being on the boat that's leaving the station and going to the new world. Once I get to the new world, the cream rises to the top. I'll take my skills, my leadership, and I'll go through it. But in the next few years, if everything's changing, I definitely want to be current." And that means you have to have a long-term focus.
My property is called The Skip. The community and everything, they all kind of come down to this word called the skip. And I chose that word because the best career advice is always not thinking about the next move, but the move after. What's the skip job? What's the skip opportunity? Well, in this world, it's not about what's the opportunity now, and what's the journey. It's about making sure that your skip opportunity is saved, and you are able to get that high salary, you're able to get one of those premier builder jobs. And that's the world that you have to have, and the mindset you have to have.
Something you mentioned earlier was really interesting, that in the next 5 years you predict that most people's jobs will be very different. What do you imagine there? Like, will there still be this product manager role? Will PMs need to move closer to engineering? What's kind of like the Venn diagrams or spectrum you're seeing of where current PMs may go?
Yeah, I definitely think that there's a world where PMs go to every industry as what I would call the agents of change. Because the PMs are the ones that can talk. They're the ones that have the broadest view of the organization, but they look at it through the technical lens. And my hope is that most of our PMs are the first to the tools and hence they're the change agents within their company.
So let's just play this out. In the next year we start to see all these product organizations changing the way they build product. And all of a sudden the way we build product is gentrified and really, really thoughtful and really far along. And then 12 months later the marketing, the sales organization, each of that company that was bought by the private equity firm, the school down the road, everything's like, "Boy, we're not current. We're going to get obsolete. Who do we bring in to be in charge of this change?" Well, this person works in the future. We need to get to the future. So I'm really bullish that product leaders are going to be like those dandelion, whatever you call it, seeds when you blow it and they just go everywhere. I have that vision.
Meanwhile, I think a lot of people going into product might be coming from design. Might be coming from data science. Might be coming from engineering because the ones that have judgment, the ones that can talk, the ones that want to stay current, they might be like, "Well, I don't necessarily want to just stay in my lane. I have a point of view as to how this should work." As you said, from a designer point of view, designers may have a lot of those skills and opinions on what it should look like. Maybe their platform won't be the pixels or the visuals, it will be the product itself and they can adjacently move into product. So, I think you're going to see this crazy influx and then this amazing kind of exodus. And then you'll also see folks that are like, "Ooh, I don't know if I can get in." So, I know that's a confusing set of three changes, but that explains why so many people have anxiety. All three of these are happening instantaneously.
There's a line, "They thought they'd buried us. They didn't know that we were seeds," that I think about.
I love that.
We're into a lot of the darker
Speaking of that, there's this hilarious tweet that just came out the other day that I have here where this guy describes the only four jobs that will remain in the future. So, the only four jobs that will exist in the future. One is product engineer/vibe coder/PM/slop cannon. Number two is security/SRE/infra person. Number three is hot people, which is like getting people to buy your stuff, customer service, and people... No, no, here's how they put it: present that easy UX to the world, is that category. And then grown-ups, which is your point of just like adults. Yeah, so.
Yeah, I read that and I agree with that. I mean, I think the adults exist and I think anyone that's at the top of their field that can talk and that essentially is opinionated, that can go broad. That's kind of the third point of hot people.
So, that reminds me. Amol, the head of growth at Anthropic, made this really interesting point that so much of his time now, more and more, is alignment as a product manager. And we were joking, what's the harder alignment problem? Aligning people in a company or like AIs, AGI? And it feels like that's a remaining piece, and it's part of what you described, somebody that can get things done, a change agent. And a big part of that is what a PM often is doing a lot of their time: creating alignment internally around what we will be doing, what we're pursuing, that kind of thing.
Yeah, and I think that if you dissect what alignment looks like, a lot of alignment was getting people the right information, the ground level truth. That problem is dramatically better. That part of the job, frankly, just absolutely sucked. Whether it was the status report or, I was on projects where there were docs that were sent to me and then I would change the doc to then send it to my boss and then that boss would send it to his, and it was just like this movement of information where the ground truth was buried in some part of the organization and then there were all these people that were putting on their spin. That, I think, is changing.
But, to your point, now someone has to decide and someone has to have an opinion on what to fight for. And that conversation is now much clearer to have because you know the ground truth, there's less spin. The CEO can literally ask their agent, "Well, what is the situation? How is this performing? What does this customer really want? How does this affect the system? Is this really something that we want to change the product to enable?" So, that conversation can happen, but now people can fight it out with real credence, right? And if you're a product person that really does have an opinion and wants to make a point, you have a forum. So, alignment won't go away. It's just not going to have as much theatrics. And I think a lot of companies that are larger do have theatrics that I think the AIs are going to remove.
And I don't know many PMs... There's some that lived for the theatrics, but frankly, most of them are like, "This just seems like a freaking waste of time." I mean, it's so telling that 80%, I bet you, if you truly ask your PM, "Do you really want your boss's boss's job? Would you want their day? Not the pay, not the credibility, not the stature, but do you want their block of back-to-back meetings?" I bet you most of them would say no. And what I'm suggesting to you is that answer's going to change in the next 2 years.
What's also really interesting is as much as this role is changing, engineering is changing even more. And what I feel like is that the engineers that will continue to thrive are basically going to become more PM-y. Because the coding part is now going to be solved. And now it's just: what should we build? Is this great? Is this the direction we want to go? What does success look like? So, if you're like, "Oh, my job is changing," just imagine being an engineer right now and how crazy that must feel.
Yeah, and I think the one advantage that engineers have is they think in systems. And they think about obsolescence more effectively. So, I think that when you make a change, you have to decide: is this change going to be sustainable in the product that you're offering? I think an engineer has an edge there. I think the other edge they have is like, "I bet you we can build this to be more automated, to be simpler." I think those are the
already goes there. Yeah.
Yeah, so I think that every one of us, like the product person, probably has a little bit of an edge in judgment and communication. The engineer is going to have a little bit of edge in the system scaling and how this change affects folks. The designer is going to have a little bit of an edge with taste. And all of these things will still remain important. And obviously people that have all of these will do better than those that have one or two, but the industry is more than safe, as evidenced by the report that there's more hiring. And I think it's going to grow. It's just a different class of individual. That's what we're trying to communicate.
The design piece is really surprising to me. The fact that this data shows that the number of design roles is plateauing and just how teams are just not valuing design as much as you'd think. Like, you would think that design becomes much more important as the number of products grows exponentially. That it's a way to stand out, to build something really beautiful and have a really thought-through experience. And it's interesting that that's not happening right now. Also, I've been thinking about how there's no world where I'm a great designer. I can't just use AI and become a great designer. Unlike an engineer, like maybe a PM, I could become a much better PM with AI. AI will do some cool stuff, but I'm never going to feel like I am a great designer now. So, it's really interesting that design isn't more successful right now with the rise of AI.
And it might be that we just don't know what to make of design in this era. That might be a piece of it. The other piece might be that just like there are product builders and then product information movers, and they're split up, I think that there are pixel generators and then there are tastemakers. And I worry that in design maybe the industry itself conflates design with more production and not with taste. And so, I think there's a lot of companies that you would talk to, and even when they were hiring a head of design, they were thinking more around, we need more production. And great designers are much more tastemakers, and I think that bias is probably entering into the hiring plans in this area that we have today.
What a wild time we are living through, Nikhyl. Holy moly.
Yeah, isn't it funny that neither of us are operational? There are days when I'm like, man, am I so happy I have the time to work on this, and then other days that I think this is some of the most interesting... being operational right now is quite a ride. And so there's good and bad, and COVID wasn't easy and there were a lot of challenges around working and seeing so much change. There's always something, but this one, everything's being questioned, including how you define joy, which I think is just absolutely fascinating.
Chaos is a ladder, as Littlefinger famously said. Nikhyl, is there anything that we haven't covered? Anything else that you think is important for people to hear? Any other advice? Anything you want to double down on before we wrap up and get to our very exciting lightning round?
I would just say that there's a lot of room to be optimistic right now. But you have to find it within yourself to recognize that there is a small period of change and exhaustion that's required to find that moment of joy. And I just urge everyone to find those reserves to get there because once you do, it's infectious. But the longer you wait, the harder it is to cross that chasm. And so I really want people to feel optimistic and find that moment of joy. But I also recognize that there is a lot of activation energy that it takes to get there, and so my hope is that... There's a lot of people going through it. And so there's some safety in numbers here, but definitely I urge everyone to try their hand at rethinking their craft.
And just to be clear, you are seeing many people in the community doing well, enjoying this, thriving. This is possible.
Yeah, it's smiling exhaustion. I see it in my community. Everyone. And before it was just exhaustion. I'll take smiling exhaustion over exhaustion. But the pace is relentless. There's nothing I can say to sugarcoat that point.
What a time to be alive. Well, Nikhyl, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?
Go for it.
What are two or three books that you find yourself recommending most to other people?
You know, Lenny, I'm not a reader. I hate to admit this, but I kind of vibe code instead of most consumption of content right now. All of the reading I do is trying to stay up-to-date, and that was a casualty. So I don't listen to as many podcasts as I want to. I don't read as much as I want to, because I have so much information coming from the agents that I have deployed and all the stuff that's going on on Reddit and X and all that. So, I don't have great book suggestions, unlike all your other guests that are great at this. They read prolifically, and I just don't. I mean, I'll tell you, I read... I don't know how much I loved it, and I'll just leave it in here in case people are interested, but
I read this book called James. James is the story of Huckleberry Finn told from Jim's point of view. I thought that was absolutely fascinating because anytime you take a classic and then you look at it through the eyes of someone else, what you realize is that story is quite powerful but very haunting. And when you read Huckleberry Finn, you're a kid. So, the distinction between seeing the innocence, not only was the book written from Twain's perspective, who was quite forward-thinking, by the way, but you remember you were a kid at the time, and now as an adult you see the book from another angle. I thought that was interesting. I don't know if I'd recommend it to your viewers or readers, but I always look for unnatural stories that exist right in plain sight. So, that was an example of that.
I think somebody else has actually recommended that book. So, that's the second mention. Next question: do you have a favorite recent movie or TV show? You've already shared some vibe coding favorites to have in the background. Anything else?
Yeah, I mean, I think everyone's talking about Paradise. If you haven't watched season 1 and season 2, it's on
Oh, is season 2 out? I didn't realize that.
Season 2 is almost wrapping up, and I haven't watched season 2 yet, but it's a little apocalyptic in nature, but it's an absolutely fascinating character drama about how people deal with very, very challenging times and what motivates individuals. The other one that I really like is Lioness, which is on Paramount+. Lioness is a story really about sort of a covert CIA
group and how they deal with, you know, protecting security for America and the importance and what it means to commit to a bigger cause. I thought that was a really well-written show. So, both of those I recommend. I do watch a ton of television and, as I mentioned, I live code to certain shows, and these two I don't live code to because I have to pay attention.
>> That's the ultimate. That's the new bar of something's great.
>> Exactly.
>> Okay, do you have a favorite product you recently discovered that you really love? Could be an app, could be some gadget, could be something else.
>> My favorite product that I've discovered of late might be kind of obvious to a lot of folks, but, you know, I'm not a car guy. So, I'll just start by saying that though I've enjoyed kind of riding the newer electric cars, I'm just not. There's a large number of people that love cars and love driving cars and, you know, talking about cars and repairing cars. That looks like the opposite of me. I just want my car to be super reliable.
And I've had a Tesla for a really long time. I've had a Model S for just a long time, and I've had it since pretty much they came out with them. And my daughter recently passed her driving exam. And because she passed her driving exam, one day my wife said, "Hey, you know, we got to get her a car." I was like, "We do?" I never actually connected the dots that she's going to need to drive a car. And I was like, "Well, where is she going to go?" And eventually I'm like, "Okay, maybe we should buy her a car, but she's not going to drive that much. Maybe I should use this as an opportunity to upgrade my car."
And so, I drove the latest Teslas that are out there, and the ones with the self-driving. And the self-driving works quite well, just to be clear. I mean, I have it now for the last month and about 95% of the time I self-drive. But the most interesting thing is I had no idea that I actually have mild anxiety when I drive that goes away when I self-drive.
And I had no idea. My wife noticed it when we were driving up to the mountains one day and it was crazy snowing and I'm like, "We're going to do it." And she's like, "You are so anxious when you drive." And I'm like, "I am." Because, Lenny, I've been driving since I was 14 years old, because I grew up in Kansas. And so, I passed the test when I was 14. So, I've been driving literally for nearly 40 years. And I had no idea, as I've gotten older, that this pressing a button and going places, it's just so awesome.
So, anyway, the reason why that experience is a change: yeah, there's the tech and all that. It's just like I look for ways to reduce my anxiety. Anything that causes anxiety, I try to eliminate at this point of my life, and this is one of them. So, that's a cool product for me.
>> I love that as a rule. I've also become all in on self-driving. I've had a Tesla for a long time, from the beginnings of their explorations into self-driving, and it was always just like, I don't know, this is scary. And now it's the opposite. Like, my wife prefers I self-drive, even though I drive well. She just feels safer when the self-driving is on.
And there's this, like, in the actual settings, they give you a stat of what percentage of your driving is self-driving, and they noted it's since 14.2, I think was the release, something like that. So, that was like the release that everyone started being like, "Wow, it's actually very good now." And I don't think a lot of people realize that it's actually incredibly good. Like, I haven't had a single concerning moment.
>> This is one of those examples in product where so many people tried the previous versions that when you then tell your friend, a lot of people have Teslas obviously in California but then across the world, when you tell your friends, a lot of people are like, "Oh yeah, I tried it and I turned it off." So, I think Tesla's got this unusual challenge of getting people to turn it back on. And obviously, the newer hardware is better than the older one, and the new software, but once you go through one experience, it can be hard to convince someone to try it again, and that's an adage in product and certainly applies here.
>> It's a downside of releasing early enough, and sometimes people just have this memory of what it might be. I feel like this is like Uber, where you almost just start hearing about it from your friends telling you, "Hey, I'm doing this thing." I'm like, "Wait, really? I guess I should try it." Yeah.
>> Yeah, so here's a Tesla suggestion for anyone who's listening: Lenny and I should be able to gift 30 days free of self-driving to our friends, people that have turned it off, because the referral plus the endorsement allows people to experience it for free, and then they can get their monthly subscription.
>> Great idea.
>> That viral plus enablement, I think it's a growth technique that, you know, they can have for free from us.
>> Such a good idea. By the way, I love Mad Max mode. I love just the personality of stuff. Are you a hurry mode guy or are you a standard mode guy?
>> I flip between them, but I'm hoping that the new release of the software keeps us in lane. Like, I don't love it changing lanes, but it's
>> Oh, like we're just trying to hurry a little bit.
>> Yeah, I wish I could just get it to go at a normal speed, but also don't change lanes, because I just don't like the rapid acceleration.
>> Okay. Next question. Do you have a favorite life motto that you find yourself coming back to in work or in life?
>> My high school quote in my yearbook still is my motto, which is "Genius is 1% inspiration, 99% perspiration," by Albert Einstein. It's something that even at an early age, and you know, it's not about genius being capital G, you know, I wasn't a New York comic. It was more like hard work is really what matters in life.
What's interesting is if you read that quote, "Genius is 1% inspiration, 99% perspiration," through the lens of AI,
>> Right.
>> it's absolutely fascinating, because it turns out the AI will do the perspiration.
>> Unlimited perspiration.
>> So, what we're leading towards is we're all moving to a world where we're all going to be inspired, and it's the inspired individuals, all of us, that will, you know, essentially continue to proliferate, and don't worry about the perspiration, but recognize that it is the perspiration that is a necessity to make things go. So anyway, I think it's an interesting quote, especially in today's era.
>> Final question. People may have noticed that we started collaborating on your podcast and your newsletter. It's such an underappreciated, under, I don't know, seen thing that you do. This podcast, this newsletter, it fills such a gap in the content out there around product building of just very tactical, important, non-sugar-coated career advice for people in product. And what I love about it is it's not AI most of the time, in spite of this conversation we just had. It's very much like, here's stuff you need to know that is not flashy and shiny AI, AI, AI all the time. So I'm going to give you a chance just to tell people about the podcast, newsletter, just what the ideas are, where they can find it.
>> I started this property called Skip because I really felt that there was a dearth of content from operators sharing best practices with emerging operators. And the idea was, look, I had been a founder before, I'd been an executive before, and I wanted to be in a position where I can say, hey, this is exactly what I experienced and this might apply to you. And I noticed that most of the podcasts and the content out there were from folks that hadn't spent as much time in operating, more time in content, and I was kind of the opposite.
Then I started building this community that I spoke about last time, which was, you know, about 20, 30 at the time; now it's over 125 heads of product who are all kind of these builders, top of their game, and kind of reinventing what product management looked like. And our goal is to collectively share our wisdom as operators to help people advance in their careers. And that calling is probably more important now than ever, as everything is changing.
And so one of the things that we're launching next month, by the time, you know, we end up launching this episode, is something called skip.help, where we have agents that have been trained on about 50 of our community leaders. And so you can go and ask a question. It might be preparing for an interview. It might be a question around navigating your current environment. It might even be, you know, how do I build a chief of staff app? And 50 of us, not just me, will respond. And this is powered by our friends at writ super me, which is a great startup that, by having these agents, you actually get the sort of wisdom of the crowds.
And so those are the things that I love. And obviously the community itself is a very curated group, and, you know, there's an infinite wait list. A lot of people want to be in it. I'm only growing it slowly because I want to maintain trust. But I do have this mailing list called skip.coach where we share our wisdom to a broader audience. So I know I've kind of gotten every single domain name that starts with skip: skip.community, skip.show, my podcast, skip.coach, skip.help. But anyway, go to any of them and you can try and get all of them.
I always appreciate, Lenny, your support and your help in building this property with me. So it's been great. You know, when I came on, I don't think I had done my podcast yet. And now I'm about ready to hit my 50th episode. And you're an inspiration, and you're past 300 obviously, and so, you know, it's fun to see how things change and how things happen. So it's been great.
>> So fun. I was going to ask you to share the domains, which you did. So it's skip.coach, skip.community, skip.show. And then there's skip
>> Skip.help is the new one.
>> Skip.help, which is launching around the time this goes out. And then you also have your Substack. I don't know if one of those takes you there, but it's theskip.substack.com.
>> Yeah, exactly. The Skip is the name of the podcast and newsletter, and skip.show takes us to both.
>> Nikhyl, thank you so much for being here. This was exactly what I was hoping. I feel like people are going to leave this feeling like, "Okay, I get it now. I understand what I need to be doing."
>> I appreciate that. And, you know, thanks for all you do for the community and for all the guests that, you know, you still have. There's probably two dozen of the folks on Skip that have been on the show or that will be on the show. So, thanks for supporting all of our efforts. We're trying to help as many product builders as possible, and that's a great journey to be on together.
>> It is. Nikhyl, thank you so much for being here.
>> Thanks, Lenny. Thanks, everyone.
>> 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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