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Jiaona Zhang (Webflow, WeWork, Airbnb, Dropbox)02 July 2023

Building minimum lovable products, stories from WeWork and Airbnb, and thriving as a PM

8Frameworks
15Insights

Episode overview

Jiaona Zhang explains why product managers should begin with user problems, earn influence rather than assume authority, and become known for a distinctive strength. Drawing on Airbnb Plus and WeWork, she shows how ambitious visions need explicit learning phases, sound unit economics, milestone-based decisions, and disciplined hiring. She also presents minimum lovable products, narrative roadmaps, ambitious OKRs, trust-building during a leader’s first 90 days, and the importance of doubling down on why customers love a product.

Key ideas

  • Start with users and their problems instead of becoming attached to a preferred solution.
  • Pair ambitious product visions with time-boxed learning phases, explicit milestones, and early unit-economics analysis.
  • A minimum lovable product should deliver a few important capabilities exceptionally well rather than many clunky capabilities.
  • Treat a roadmap as a written story organized around strategic themes, with live execution artifacts linked from it.
  • Define OKRs around what meaningful success would feel like for users and the business; missed ambitious targets should produce learning, not punishment.
  • Accelerate a PM career by becoming excellent—and visibly reliable—at a distinctive kind of work.
  • In a new leadership role, build broad context and trust before spending social capital on major changes.
  • Understand why customers love the core product, invest deeply there, and use that advantage when expanding into adjacent products.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Self-Mastery5 steps

Be Known For Something

Pick one thing to be excellent at, get a reputation for it, and let responsibility flow to you

Read →
Influence5 steps

Disagree With the Founder Via the Spirit

Never say no to the idea — say yes to the spirit and come back with a better path

Read →
Strategy5 steps

Double Down on Why People Love You

Name the core reason users love you, keep investing in it, and build every new product off it

Read →
Strategy5 steps

Phase-Bounded Big Bets

Dream big, but chunk the bet into named learning phases with quarterly go/no-go gates

Read →
Leadership5 steps

Spirit-First OKRs

Write down qualitatively what crushing it looks like before you pick any number

Read →
Innovation5 steps

The Minimum Lovable Product (MLP)

Ship five things people love, not fifteen things that merely work

Read →
Strategy5 steps

The Roadmap Is a Story, Not a Spreadsheet

Lead with themes and a narrative; link out to the systems for the granular how

Read →
Leadership6 steps

The Time-Boxed First 90 Days

Build context 5x faster, leave a plan behind, and don't spend trust you haven't banked

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 7

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “welcome to Lenny's podcast where I interview world-class product leaders and growth experts”

    ▶ Watch at ~0:30approx.
  • Jiaona ZhangMentionsJay-Z is senior vice president of product at webflow she's also a lecturer at Stanford teaching a course on product management

    “Jay-Z is senior vice president of product at webflow she's also a lecturer at Stanford teaching a course on product management”

    ▶ Watch at ~0:30approx.
  • Brian CheskyMentionsBrian chesky at Airbnb there was a whole article where we unpacked this moment in their product development cycle

    “Airbnb and Brine and many great leaders are famous for Imagining the ideal situation”

    ▶ Watch at ~11:00approx.
  • Mike LewisMentionsmentioned

    “I remember talking to one of our colleagues Mike Lewis who is leading a different team with an Airbnb”

    ▶ Watch at ~13:30approx.
  • Jared LetoMentionsmentioned

    “the movie on we work with Jared Leto how similar to reality was that”

    ▶ Watch at ~43:00approx.
  • Julie ZhuoCoinedJulie was a long time design leader at Facebook she's now the founder of a company called Sundial

    “I also really like Julie's book around managing people how to be like a good manager”

    ▶ Watch at ~58:30approx.
  • Brandon SandersonRecommendsmentioned

    “I'm a big fan of Brandon Sanderson he completed The Wheel of Time series”

    ▶ Watch at ~59:00approx.

Resources · 35

  • Stanford UniversityMentionsplace

    “she's also a lecturer at Stanford teaching a course on product management”

    ▶ Watch at ~0:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “welcome to Lenny's podcast where I interview world-class product leaders and growth experts”

    ▶ Watch at ~0:30approx.
  • Pocket GemsMentionscompany

    “she's also pm at Dropbox and at a gaming company called pocket gems”

    ▶ Watch at ~1:00approx.
  • WeWorkMentionscompany · Adam Neumann and Miguel McKelvey

    “before this she was senior director of product management at wework”

    ▶ Watch at ~1:00approx.
  • AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

    “a long time product leader at Airbnb where I got to work with Jay-Z”

    ▶ Watch at ~1:00approx.
  • DropboxMentionscompany · Drew Houston and Arash Ferdowsi

    “she's also pm at Dropbox and at a gaming company called pocket gems”

    ▶ Watch at ~1:00approx.
  • Brave SearchMentionswebsite · Brave Software

    “today's episode is brought to you by Brave search and their newest product the brave search API”

    ▶ Watch at ~1:30approx.link ↗
  • Brave BrowserMentionssoftware · Brave

    “thanks to being the default search engine in the brave browser”

    ▶ Watch at ~2:30approx.
  • Brave Search APIRecommendstool · Brave Software

    “listeners can get started testing the API for free at brave.com Lenny”

    ▶ Watch at ~3:00approx.
  • MiroUsessoftware · Miro

    “actually used Miro to collaborate with the Miro team on creating my own board”

    ▶ Watch at ~4:00approx.
  • Airbnb PlusMentionsproduct · Airbnb

    “we're working on this concept called Airbnb Plus”

    ▶ Watch at ~7:00approx.
  • JiraUsessoftware · Atlassian

    “if your team uses jira go ahead and Link out to jira”

    ▶ Watch at ~25:30approx.
  • ReforgeMentionscompany · Brian Balfour

    “I'll give a plug for a new thing coming out of reforge”

    ▶ Watch at ~26:00approx.
  • Microsoft OutlookMentionssoftware · Microsoft

    “built to work with Gmail and Outlook”

    ▶ Watch at ~27:00approx.
  • GmailMentionssoftware · Google

    “built to work with Gmail and Outlook”

    ▶ Watch at ~27:00approx.
  • SuperhumanRecommendssoftware · Superhuman

    “try one month free at superhuman.com Lenny”

    ▶ Watch at ~27:30approx.
  • Silicon ValleyMentionsplace · Mike Judge, John Altschuler, and Dave Krinsky

    “same way of like why haven't watched Silicon Valley you're like it's a little too close to home”

    ▶ Watch at ~43:00approx.
  • WeCrashedMentionstv show

    “the movie on we work with Jared Leto how similar to reality was that”

    ▶ Watch at ~43:00approx.
  • SlackMentionssoftware · Slack Technologies

    “slack is really taking off why don't we build you know a like a like a slack competitor”

    ▶ Watch at ~52:30approx.
  • The Design SprintRecommendsbook · Google Ventures

    “I love the design Sprint by Google”

    ▶ Watch at ~58:30approx.
  • The Making of a ManagerRecommendsbook · Julie Zhuo

    “I also really like Julie's book around managing people how to be like a good manager”

    ▶ Watch at ~58:30approx.
  • The Wheel of TimeRecommendsbook · Robert Jordan

    “I'm a big fan of Brandon Sanderson he completed The Wheel of Time series”

    ▶ Watch at ~59:00approx.
  • Tress of the Emerald SeaRecommendsbook · Brandon Sanderson

    “the latest one is the trust by the emerald C that I really love”

    ▶ Watch at ~59:00approx.
  • MistbornRecommendsbook · Brandon Sanderson

    “he you know he has the mistborn series and so he he's a great one”

    ▶ Watch at ~59:00approx.
  • YouTubeUseswebsite · Google

    “we don't we don't do TV but we do do YouTube songs”

    ▶ Watch at ~1:00:00approx.
  • ArcaneRecommendstv show

    “when Arcane was made both my husband and I were like what how did we predict this is amazing”

    ▶ Watch at ~1:00:30approx.
  • SNOORecommendsproduct · Happiest Baby

    “I do love this new and it's very top of mind because I just graduated my second son from the snoo”

    ▶ Watch at ~1:02:00approx.
  • The Jungle BookMentionsfilm

    “he's obsessed with Jungle Book wearing a fire hat next to a fire truck”

    ▶ Watch at ~1:02:30approx.
  • MidjourneyRecommendssoftware · Midjourney, Inc.

    “a mid-journey for your toddler is actually great”

    ▶ Watch at ~1:02:30approx.
  • Webflow UniversityRecommendscourse · Webflow

    “we're really going to bring the magic of wetful University the magic of AI all together”

    ▶ Watch at ~1:05:00approx.
  • ReforgeMentionscompany · Brian Balfour

    “I'm actually working on a course another course for through reforge which is around managing your PM career”

    ▶ Watch at ~1:06:00approx.
  • WebflowUsessoftware · Webflow

    “my website which is built in webflow”

    ▶ Watch at ~1:06:30approx.
  • SpotifyMentionssoftware · Spotify

    “you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”

    ▶ Watch at ~1:07:00approx.
  • Apple PodcastsMentionssoftware · Apple Inc.

    “you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”

    ▶ Watch at ~1:07:00approx.
  • Lenny's PodcastMentionspodcast · Lenny Rachitsky

    “you can find all past episodes or learn more about the show at lennyspodcast.com”

    ▶ Watch at ~1:07:00approx.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster05:00

The Biggest Mistake New PMs Make: Jumping to Solutions

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