Jiaona Zhang says the hardest habit to untrain in new PMs is getting attached to a solution they can already picture building, instead of starting with users and their real problems. A related misconception is that PMs get to call the shots; in reality they have little formal authority and lead through influence.

New PMs fixate on a solution they can see in their head rather than a user problem
The first step is to understand people's problems, then judge whether an opportunity exists
PMs are not CEOs and manage no one; the job is influence, not authority
The role is about hearing opportunities and editing possibilities, not deciding what gets built

“you get really attached to a solution a way of implementing something something that you you can see in your head that you want to…”
Jiaona Zhang · 05:00

“you're not a CEO you're not here you actually have very little true Authority because you don't actually manage anyone it's a lot of it…”
Jiaona Zhang · 05:30

#product management#career#user research

Hot Take· 2

Hot Take31:30

On OKRs: Prefer Red Over All-Green

Zhang's biggest OKR tip is to get crisp on what qualitatively would make you say you did a great job. Too much fear around OKRs causes sandbagging and slow innovation; she'd rather see red or yellow with real learning than all-green, which signals unambitious targets. The worst outcome is hitting every OKR while users and the company feel nothing different.

Define qualitatively what 'crushing it' looks like for users and the business
Fear of missing OKRs drives sandbagging and hesitant targets
All-green means the OKRs weren't ambitious enough
Hitting every OKR while nobody feels a difference is the worst result

“I would rather have all the okrs be red or yellow and like we missed everything and we learned around why we missed it then…”
Jiaona Zhang · 32:30

“you end up hitting all your okrs but the company and and your users at large are like I don't feel anything different”
Jiaona Zhang · 33:30

#okrs#goal setting#leadership

Hot Take1:02:00

AI Shifts Humans From Execution to the Creative Process

Zhang uses Midjourney with her toddler instead of instant-gratification phone videos, prompting detailed images like a fire truck with a fire hat next to Jungle Book. She sees this as a preview of the future: humans will increasingly focus on the creative process and the idea, while AI handles executing the pieces, so training that creative muscle matters.

Midjourney replaces instant phone videos with a wait-and-create ritual for her toddler
Kids can prompt specific, imaginative images instead of passively consuming
The future of human work centers on ideas and the creative process
Executing the pieces matters less; framing what you want to bring to life matters more

“a mid-journey for your toddler is actually great”
Jiaona Zhang · 1:02:30

“so much of what we are going to be doing as as humans is literally like what is the creative process what's the idea it's…”
Jiaona Zhang · 1:03:00

#ai#creativity#future of work

Explainer· 5

Explainer11:30

How to Think Big Without Betting the Whole Company

Zhang argues you should pair a big vision with thoughtful execution by being explicit about what phase you're in. Set short learning phases with named things you're trying to learn, do unscalable prototyping to learn them, and put quarter-long go/no-go milestones in place so you can kill a path after a quarter instead of sunk-costing into two years.

Couple a big vision with thoughtfulness about execution
Be explicit with the team about which phase you're in (learning vs building)
Do unscalable things in the prototyping phase to learn specific lessons fast
Set quarter-long milestones as go/no-go checkpoints to avoid sunk-cost traps

“you got a couple of that really big Vision with thoughtfulness around your execution”
Jiaona Zhang · 11:30

“every single point it was a go and no go and I think that really can help a team and a company say it's okay…”
Jiaona Zhang · 13:30

#product strategy#execution#prioritization

Explainer16:30

Minimal Lovable Product vs Minimal Viable Product

Zhang popularized the minimal lovable product as the new MVP: in a crowded market, barely meeting a quality bar isn't enough, so you must understand what a lovable experience is for your specific users. Your polish bar can be lower when you're replacing a painful manual workflow, and it's better to do five things with high polish than fifteen things that all feel clunky.

In a world of many options, 'barely usable' no longer wins
The right polish bar depends on your users and what you're replacing
Replacing spreadsheets or manual workflows lets you ship at a lower bar
Prefer five deeply lovable features over fifteen merely viable ones

“minimal level products is the new MVP right the new uh minimal viable product”
Jiaona Zhang · 17:30

“it's like better to do five things instead of the 15 things”
Jiaona Zhang · 20:00

#product strategy#mvp#webflow

Explainer20:30

What Makes a Product Lovable: Polish and Pixie Dust

Zhang describes lovability as the product simply being good, high quality, and not janky, plus small touches that power users adore, like keyboard shortcuts. Beyond table stakes, you scatter 'pixie dust', a bit more than users expect, in a few chosen areas, since staffing and timeline mean you can't do it everywhere.

Baseline lovability is the product being genuinely good and not janky
Small power-user touches like keyboard shortcuts create outsized love
'Pixie dust' means doing a little more than users expect in select areas
You can't pixie-dust everything; pick a few areas within your time and scope

“keyboard shortcuts right like that she feels small but like that is a piece that creates a lot of love love from user base who…”
Jiaona Zhang · 21:00

“I'm gonna scatter that pixie dust I'm gonna do a little bit more than what users are expecting and that creates that lovability”
Jiaona Zhang · 22:00

#product design#delight#polish

Explainer43:30

First 90 Days: Build Context Fast, Across Every Function

Joining Webflow in her third trimester, Zhang had a time-boxed first 90 days before maternity leave. The core job of any first 90 days is to build context well; her twist was doing it roughly five times faster by mapping who to talk to across functions and levels, from leadership to long-tenured engineers, and packing early weeks with those meetings, then leaving a strategic plan in place.

The core of any first 90 days is building context well
Talk across functions and levels, not just your peers and team
She scheduled 40-50 conversations, pairing each function's leader with someone close to the work
Left a strategic plan and research assignments before going on leave

“the most important thing for anyone's for assigning days is to build context and to build context well”
Jiaona Zhang · 44:00

“it's not just with your peers it's not even just with your team but to really think across all the different functions”
Jiaona Zhang · 45:30

#onboarding#leadership#webflow

Explainer51:30

The Cross-Company Lesson: Understand Why People Love You, Then Double Down

Zhang's single biggest product lesson across Dropbox, Airbnb, WeWork, and Webflow is to understand why people love you and keep investing deeply in that core. Dropbox chased a Slack competitor instead of client sync performance; Airbnb dabbled in inspection, experiences, and transport instead of its homes; WeWork over-invested in tech instead of inventory. Build new products around your core advantage, not away from it.

Dropbox's Alpha is your files and simplicity, not a chat clone
Airbnb's magic is real homes from real people, not managed inventory
WeWork's core is inventory management, not futuristic key-card tech
When you build a new product, leverage the core advantage instead of spreading thin

“why do people love Dropbox and what do we need to do to keep investing in that”
Jiaona Zhang · 53:00

“understand why people love you double down on that and then whatever else you build around it”
Jiaona Zhang · 56:00

#product strategy#focus#dropbox

Story· 2

Story06:30

Airbnb Plus: Her Biggest Product Mistake

Zhang tells the untold story of Airbnb Plus, where the team went solution-first and competitor-afraid, deciding to inspect and manage inventory. The real problem was that guests wanted to know what they were getting, better solved through reviews, lock boxes, and cleaning partnerships than by sending inspectors. She believes the unit economics never would have worked and the team should have pressure-tested them at the start.

The team was solution-first and reacting to the rise of managed marketplaces
Inspecting inventory ignored Airbnb's actual weakness: it had no operations muscle
Cheaper, tailored fixes (reviews, lock boxes, local cleaners) beat one blunt inspection instrument
Magical thinking about unit economics 'at scale' should have been checked up front

“I do think we were very solution first and I think we're also competitor afraid at the time”
Jiaona Zhang · 07:00

“I personally don't believe the unit economics ever would have really worked out I think we should have known that”
Jiaona Zhang · 10:30

#airbnb#product strategy#unit economics

Story41:00

Pregnant at WeWork, She Put Herself on the Layoff List

During the WeWork layoffs, Zhang was in her first trimester and faced a choice: stay in a guaranteed role with maternity leave, or give that role to a team member she had recruited. She felt responsible for someone she'd hired who was on a visa and had limited time to find a new job, so she put herself on the layoff list and handed them the role.

She was pregnant and could have kept a secure role with maternity leave
She felt responsible for people she had personally convinced to join
A team member on a visa had far less runway to find a new job
She chose to lay herself off and give that person the role

“I was actually in my first trimester when we were going through all of these layoffs”
Jiaona Zhang · 41:00

“am I gonna take this new role or am I going to put myself on the layoff list essentially and and give the role to…”
Jiaona Zhang · 41:30

#wework#leadership#empathy

Q&A· 1

Q&A14:30

How to Push Back on a Founder Who's Bought Into a Bad Idea

Asked how to disagree with a leader who's committed to something, Zhang says it starts with whether you have true conviction; if you do, saying no is your job. The technique is to understand the spirit of what they're trying to achieve, get aligned on that goal, and come back with better, data-backed options rather than just objecting.

First test whether you have real conviction or are still learning
With conviction, saying no is doing your job
Anchor on the spirit of what the leader is trying to accomplish for user and business
Return with better options and the data behind them, not just a rejection

“if you're like I have total conviction then your job is to say no”
Jiaona Zhang · 14:30

“when you come back with a much better solution and you have the data and you have the thinking behind it it's very”
Jiaona Zhang · 16:00

#leadership#influence#product management

Takeaway· 4

Takeaway28:00

Accelerate Your PM Career by Being Known for Something

Zhang's top career tip is to become excellent at, and known for, a specific thing, whether shepherding complex launches, tackling technically hard problems, or navigating regulatory complexity. When you're known for something you get handed those projects, crush them, and earn more responsibility. Early on, her reputation was built on a strong analytics background and execution.

Pick a specialty and become the person known for it
Reputation attracts responsibility; people flock to proven experts
Her early edge was analytics and keeping many plates spinning on execution
As you move into management, the strength you flex evolves beyond pure execution

“find something that you can be really really good at”
Jiaona Zhang · 28:30

“much of what I just heard is you just worked incredibly hard and just got [ __ ] done”
Lenny · 31:00

#career#product management#reputation

Takeaway36:00

WeWork Lessons: Empathy and Not Over-Hiring

From her year at WeWork during the 2019 crisis, Zhang took two lessons. The people lesson was empathy: after growing a global team she had to figure out transition plans as layoffs hit. The org lesson was to not over-hire, using clear milestones and gates to unlock hiring, because laying off people you personally hired is a terrible thing to have to do.

Spent the first six months growing a global team, then managing layoffs
Leadership empathy and fair transition plans matter most in downturns
Don't over-hire; gate hiring behind clear milestones and results
Laying off people you hired is painful and avoidable with hiring hygiene

“the second lesson really was around not over hiring and so I think that was huge”
Jiaona Zhang · 37:30

“literally having hired people and then having to let them go it's not something you want to do”
Jiaona Zhang · 38:00

#wework#leadership#hiring

Takeaway49:00

Trust Is a Piggy Bank: Don't Push for Change Before You've Earned It

Reflecting on her first 90 days, Zhang admits she pushed too hard for change too fast because of the time constraint. Her lesson: treat trust like a bank where you deposit before you withdraw. You spend social capital to push for change, so be thoughtful about how full the piggy bank is before you start spending it.

The time-boxed 90 days made her push for change too quickly
Gain trust first, then use it to push for change
Trust is social capital: deposit before you withdraw
Check how full your trust bank is before spending it

“I was almost pushing too hard I was pushing too hard for change”
Jiaona Zhang · 49:00

“really thinking about your trust as like a bank right it's like you're putting money into your bank and then at some point you're gonna…”
Jiaona Zhang · 49:30

#leadership#trust#change management

Takeaway56:30

The Best Advice She Got: Ask for Help

Zhang's most impactful advice is to ask for help, even as the leader everyone looks to. It feels counterintuitive when people expect you to have the answers, but sitting alone with your problems keeps you stuck at something short of the global best. Being honest about what you know and don't, and seeking mentorship and input, is a core principle for her.

Leaders feel pressure to have it together and not ask for help
Not asking leaves you stuck with a suboptimal answer in your own head
Be honest about what you know and don't know
She currently asks founders and engineers for help on Webflow's AI strategy

“if you don't ask for help there's so many times where you're just gonna be sitting there with your problems”
Jiaona Zhang · 57:00

“be honest about what you know and what you don't know and ask for help when you don't know something”
Jiaona Zhang · 57:30

#leadership#mentorship#career

Frameworks in this episode

Be Known For Something

Disagree With the Founder Via the Spirit

Double Down on Why People Love You

Phase-Bounded Big Bets

Spirit-First OKRs

The Minimum Lovable Product (MLP)

The Roadmap Is a Story, Not a Spreadsheet

The Time-Boxed First 90 Days

Insights & moments

⚡Myth Buster· 1

The Biggest Mistake New PMs Make: Jumping to Solutions

◆Hot Take· 2