Why half of product managers are in trouble | Nikhyl Singhal (Meta, Google)

The job has shifted fast—what used to make great product managers isn’t the center anymore, and the role is under real pressure.

The information‑shuttling PM is fading; the industry’s on edge, but it’s also a rebirth where builders thrive and those who don’t love building are exposed.

Today I’m welcoming Nikhyl Singhal—my go‑to on product careers—longtime exec at Meta and Google, former CPO at Credit Karma, four‑time founder, and the force behind the Skip communities and podcast; this is straight talk for PMs on what’s changing and what to do now.

Glad to be back, Lenny—version two and ready to share what I’m seeing.

Set the scene: what’s gotten better, and what should worry PMs?

We went from pushing decks and status to actually building, testing, and touching customers—comp is up and options are wide—but the pace is relentless and mid‑career folks feel stretched by work, family, and constant change.

Are people net better than a few years ago, or melting down?

Top players feel stronger and more engaged, yet even they’re stressed about keeping up and not getting run over.

Looking ahead a couple years, what changes most?

Teams are wiring in agents and chief‑of‑staff apps, stripping out mechanical work so PMs focus on judgment while shipping many more changes at far lower cost.

When you say judgment, what do you mean?

It’s system‑level calls about what to build, what not to build, when it’s truly good, and whether it keeps the product distinct and maintainable; with this acceleration, tolerance for bad software collapses.

I often just ask AI, how do we make this experience better, and it surfaces strong, shippable ideas.

Exactly—super‑skills will sweep app stores and harden experiences, which is why there’s real optimism.

Even non‑elite teams now have elite help through AI, which levels quality fast.

Legacy stacks and missing owners held companies back, but AI lets us finally fix crusty systems—and I expect heavy layoffs followed by lean rehiring of AI‑first builders.

Timely data point: open PM roles are at a multiyear high, which fits your thesis that deciding what to build still matters.

The market wants builders across functions, while pure coordinators age out; in this era, hands‑on beats slide‑ware.

Shipping with AI feels like compounding progress, which is addictive.

You can finally get immediate wins without waiting in line—builders are bleeding into other functions, more PMs are founding, and even CHRO roles want product DNA, while non‑builders may need a reset outside core tech.

A growth PM at Anthropic argued engineers move so fast that PM leverage is in alignment and staying on top of the firehose, not being a shadow coder.

Totally—don’t out‑engineer engineers, build the internal system that scales judgment by automating reviews, standups, status, and prioritization.

Right—make yourself scale through software, and it’s fun because you’re building your own tools.

We’ll still need grown‑ups with wisdom who can move fast, but I worry diversity and geography backslide as founders hire in their own image and pace squeezes caregivers; also, big logos matter less than how modern your craft is.

So brand names can even hurt if they signal old ways, and interviews now probe tools, scenarios, and taste.

Exactly—past hallway wins sound flat if you can’t show current methods and hands‑on impact.

So the skill stack is inverted.

We prized factory‑building over car‑fixing for years; now we want your opinion and what you can personally ship.

Give PMs concrete advice for this new world.

Humans resist reinvention, especially in our power years when we juggle too much, but you have to cross the mental threshold and choose to stay current even as the target moves.

Leaders admit they’d slow AI if everyone did, but that’s not how the game works—so accept the speed and lean in.

We’ve seen this movie—hardware‑style PM collapsed into internet PM—chaos first, then a new steady state; this sprint won’t last forever, but now’s the moment to modernize.

The upside is real: higher comp, more roles, fewer blockers, and work that finally feels like progress.

Find your first joy moment with AI—once something you built saves you time or delights a user, the fear fades and energy returns; if you still hate it, consider a different lane.

What’s in your stack, and what have you vibecoded?

I’ve been deep on Claude, building agents for my community—auto‑matching members, routing jobs to the right people, and answering questions on content—guided by a lifelong habit of automating myself out of work.

Best path is solving your own pain—ask AI in plain English to build the thing you want, and iterate together.

You don’t need to be an engineer—bring clear taste and intent, then let the agent handle the heavy lifting, and the lightbulb goes on.

PMs can actually enjoy the job a lot more in this version of the craft.

The noise of change masks that truth, and most people will switch roles within five years anyway—focus on making the best of it.

Say we’re in—beyond that first joy, how do we thrive?

Turn up your pace, carve time, drop the title ego, take smaller scopes to stay current, and play the long game so your next‑after‑next move is premium.

Where do PMs end up on the org map?

PMs become change agents across every function and even outside tech, while design, data, and engineering flow into PM as lines blur—hence the anxiety of simultaneous influx and exit.

Alignment still matters, maybe more.

Theater falls away as ground truth is automated, and alignment becomes clear decisions and tradeoffs, which makes big leadership jobs more appealing.

Engineering is transforming too.

PMs keep an edge in judgment and communication, engineers in systems and automation, designers in taste—hiring’s up, but for a different profile.

Before the lightning round, any final guidance?

Be optimistic, accept a short burst of hard change to reach joy, and don’t wait—the longer you delay, the steeper the jump.

Quick lightning starters: books, shows, a product you love, and a motto?

I read less now but liked James for its fresh lens; I’m into Paradise and Lioness; Tesla’s self‑driving cut my driving anxiety; and my north star is inspiration over perspiration—especially now that machines handle much of the sweating.

Give folks the Skip rundown so they can go deeper.

Skip shares operator wisdom through a curated CPO community, a broader Skip Coach list, the Skip Show podcast, and soon skip.help, where agents trained on dozens of leaders answer your career and operating questions.

Before we wrap, where should folks find you online? You mentioned skip dot coach, skip dot community, skip dot show, the new skip dot help, and the Substack.

That’s right. The Skip is the podcast and newsletter, and those links take you to both.

Thanks so much for doing this—this hit exactly what people need, and I think listeners now know what to do.

Appreciate it, and thanks for everything you do for the community. Dozens of folks in Skip have been or will be on this show, and we’re all pushing to help as many product builders as we can.

It is, Nicole. Thanks for being here, and thanks, Liddy.

Thanks for listening. Subscribe on Apple Podcasts, Spotify, or your favorite app, leave a rating or review, and find past episodes at lennyspodcast dot com, then see you next time.