Maggie Crowley (Toast, Drift, Tripadvisor)05 November 2023

Mastering product strategy and growing as a PM

5Frameworks

14Insights

Episode overview

Lenny Rachitsky interviews Maggie Crowley about the habits that distinguish exceptional product managers: simplifying priorities, following up on results, and doing unglamorous work to deliver outcomes. Crowley explains a detailed, evidence-heavy approach to product strategy that connects company mission and market context to opportunities, challenges, proposed solutions, and an execution plan. They also discuss breaking into product management, the risks of overvaluing quantitative data and rigid frameworks, and how publishing practical content accelerated Crowley’s career.

Key ideas

Great product managers simplify complexity, commit to a small number of priorities, and sustain team energy until the work ships.
Following up on launch results improves learning while demonstrating to managers that the PM reliably closes loops.
A PM is responsible for the customer and business outcome, so unglamorous work in support, sales, QA, implementation, copy, and project management may become their job.
Product expertise requires repeated shipping cycles and enough time to observe the consequences of earlier decisions.
A product-strategy document should connect the mission, landscape, current state, technical hurdles, opportunity, challenges, proposed solution, and execution plan.
A one-pager should clearly state the background, problem, why the problem matters, and why it matters now, then invite engineering and design partners to challenge it.
Claims of being highly data-driven can signal overreliance on dashboards; qualitative research and judgment are needed to understand why behavior occurs.
Product frameworks are tools rather than universal rules, and publishing useful, authentic lessons can build relationships, recruiting reach, and deeper learning.

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

Frameworks in this episode

Communication5 steps

Ruthless Simplification for PM Writing

A set of concrete tools to strip PM documents down to only what's necessary.

Read →

Communication3 steps

Start-With-Why One-Pager

The PM's core artifact: define the thing by nailing the problem and why-now before anything else.

Read →

Mindset3 steps

The Data-Driven Red Flag

When someone brags about being 'data-driven,' suspect weak product judgment, not strong analytics.

Read →

Strategy8 steps

The Landscape-First Product Strategy Doc

A bullet-driven Google Doc that builds an unbroken logic chain from company mission down to a single team priority.

Read →

Leadership3 steps

The Three Threads of Great PMs

The three durable behaviors that separate great product managers from good ones, in any company type.

Read →

People & resources mentioned

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

People · 11

Maggie CrowleyMentionsI've actually been going through old episodes of Maggie Crowley's podcast that she did when she was at drift
“today my guest is Maggie Crowley Maggie is currently vice president of product at toast”
▶ Watch at ~0:30approx.
Maggie CrowleyMentionsI've actually been going through old episodes of Maggie Crowley's podcast that she did when she was at drift
“she was also an Olympic speed skater”
▶ Watch at ~1:00approx.
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
“use promo code Lenny to get 75% off your first year”
▶ Watch at ~2:30approx.
Bill CarrMentionsbill joined Amazon just 5 years after it was founded stayed there for 15 years
“this chat with Bill Carr that I had who was an early Amazon exec”
▶ Watch at ~46:30approx.
Adam MedrosMentionsa VP product Tri advisor
“Adam medros who was a VP product Tri advisor”
▶ Watch at ~1:00:00approx.
Albert EinsteinMentionsThere's that great Einstein quote about insanity being repeating things that you're doing, expecting a different outcome.
“a guest who shared this quote that is stuck with me from Einstein”
▶ Watch at ~1:11:00approx.
Steve JobsMentionsSteve Jobs is just uh the bar he held for the company and for technical talent and for excellence was not uh wavering.
“the presentation secrets of Steve Jobs”
▶ Watch at ~1:15:00approx.
Annie DukeCoinedAnnie is the author of the bestselling book thinking in bets and also her more recent book quit
“thinking in bets by Annie Duke is the second one”
▶ Watch at ~1:15:30approx.
Claire Hughes JohnsonCoinedClaire was most recently Chief Operating Officer at stripe for the past seven years
“the scaling people book by Claire Hughes Johnson”
▶ Watch at ~1:16:00approx.
Gary OldmanRecommendsmentioned
“slow horses Gary Oldman is incredible highly recommend”
▶ Watch at ~1:16:30approx.
John CutlerMentionsI talked to John Cuddler actually and he gave me this framework that is like completely stuck in my mind
“I get to work with John Cutler it's phenomenal”
▶ Watch at ~1:21:30approx.

Resources · 41

ToastMentionscompany
“Maggie is currently vice president of product at toast”
▶ Watch at ~0:30approx.
Charlie HealthMentionscompany
“prior to this she was VP and head of product at Charlie Health”
▶ Watch at ~1:00approx.
Harvard Business SchoolMentionsplace
“she's also got an MBA from Harvard Business School”
▶ Watch at ~1:00approx.
TripadvisorMentionscompany
“product manager at Trip Advisor”
▶ Watch at ~1:00approx.
BefspotMentionscompany
“director of product at bef spot”
▶ Watch at ~1:00approx.
DriftMentionscompany
“senior director of product at drift”
▶ Watch at ~1:00approx.
IgnitionCoinedsoftware · Ignition
“as part of ignition's broader goto Market operating system”
▶ Watch at ~2:00approx.
Productroadmap.comRecommendssoftware · Ignition
“to sign up go to product Road map. and use promo code Lenny”
▶ Watch at ~2:30approx.
DiscordMentionssoftware · Discord Inc.
“a Discord community of 2500 traders to discuss your ideas”
▶ Watch at ~3:00approx.
ComposerRecommendssoftware · Cursor
“head to composer. trade and use the code Lenny for an extra week of free trial”
▶ Watch at ~3:30approx.
On Writing WellRecommendsbook · William Zinsser
“there's this book I read called on writing well that is one of the most impactful books for writing for me”
▶ Watch at ~14:00approx.
NotionUsessoftware · Notion Labs
“you're using notion and you have your three bullets expanding”
▶ Watch at ~15:00approx.
AmazonMentionscompany · Jeff Bezos
“an ex Amazon guy that's one of their principles at Amazon”
▶ Watch at ~16:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“at Airbnb one of the core values that are being be for time was simplify”
▶ Watch at ~17:00approx.
The Pyramid PrincipleRecommendsbook · Barbara Minto
“put the headline the full conclusion first and then you're supporting argument second”
▶ Watch at ~18:30approx.
The Pyramid PrincipleMentionsbook · Barbara Minto
“pyramid principle yeah yes everyone should do that”
▶ Watch at ~18:30approx.
SlackUsessoftware · Slack Technologies
“we just have a little group chat that is focused on product”
▶ Watch at ~20:30approx.
WeWorkUsescompany · Adam Neumann and Miguel McKelvey
“she and I spent four months working together in a in a Wei workor in person”
▶ Watch at ~32:30approx.
Google DocsUsessoftware · Google
“what I did was I just wrote out a Google doc”
▶ Watch at ~35:30approx.
TwitterMentionswebsite · Twitter
“people can just bother you on Twitter and ask Maggie where's that template”
▶ Watch at ~39:30approx.
TwitchMentionscompany
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~44:00approx.
DraftKingsMentionscompany
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~44:00approx.
ClickUpMentionssoftware · ClickUp
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~44:00approx.
SnowflakeMentionscompany · Snowflake Inc.
“built by alums of airbeam be and snowflake for modern growth teams”
▶ Watch at ~44:00approx.
MiroMentionssoftware · Miro
“companies like twitch Muro clickup and DraftKings rely on EPO to power their experiments”
▶ Watch at ~44:00approx.
EppoRecommendssoftware · Eppo
“check out EPO at geo.com Lenny and 10x your experiment velocity”
▶ Watch at ~45:00approx.
LinearMentionssoftware · Linear
“the founder of linear talked about this concept of side quests”
▶ Watch at ~53:00approx.
FigJamUsessoftware · Figma, Inc.
“product review template for fig Jam love that one use that one all the time”
▶ Watch at ~1:03:30approx.
FigmaUsessoftware · Figma
“there was a newsletter article about figma and they they had some templates”
▶ Watch at ~1:03:30approx.
The Presentation Secrets of Steve JobsRecommendsbook · Carmine Gallo
“most common one is probably the presentation secrets of Steve Jobs”
▶ Watch at ~1:15:00approx.
Thinking in BetsRecommendsbook · Annie Duke
“thinking in bets by Annie Duke is the second one”
▶ Watch at ~1:15:30approx.
Scaling PeopleRecommendsbook · Claire Hughes Johnson
“the scaling people book by Claire Hughes Johnson I really enjoyed”
▶ Watch at ~1:16:00approx.
Slow HorsesRecommendstv show · Will Smith
“slow horses Gary Oldman is incredible highly recommend”
▶ Watch at ~1:16:30approx.
LadderUsesproduct
“I'm now on ladder fit”
▶ Watch at ~1:17:30approx.
FutureUsesproduct · Future
“I am I use it three times a week”
▶ Watch at ~1:17:30approx.
Pump LogRecommendssoftware
“there's this app called pump log I have never seen an execute so well on one problem”
▶ Watch at ~1:18:00approx.
ToastRecommendscompany
“check out toast and use toast when they're at restaurants”
▶ Watch at ~1:21:00approx.
LinkedInMentionswebsite · LinkedIn
“I LinkedIn but to speaking of cringe like I just can't get into LinkedIn posting”
▶ Watch at ~1:21:00approx.
Apple PodcastsRecommendssoftware · Apple Inc.
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:22:00approx.
SpotifyRecommendssoftware · Spotify
“you can subscribe to the show on Apple podcast Spotify or your favorite podcast app”
▶ Watch at ~1:22:00approx.
Lenny's PodcastCoinedpodcast · Lenny Rachitsky
“you can find all past episodes or learn more about the show at Lenny podcast.com”
▶ Watch at ~1:22:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

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

Hot Take· 4

Hot Take10:00

Strategy Is Only 5% of the PM Job — Shippers Beat Strategists

Maggie pushes back on the idea that strategy is the core PM skill. She argues strategy is one tiny slice — maybe 5% — of the work, and that a PM who ships more, gets more reps, and creates real impact will out-perform someone with a great strategy whose work never leaves the building.

Strategy matters but is roughly 5% of a PM's actual work
The PM who ships more and gets more reps beats the one with the best strategy
Communication and analytical ability are basics, not what makes you great
If your stuff isn't getting out the door, strategy skill won't save you

“you do a strategy but it's 5% of the work that you do”
Maggie Crowley · 10:00

“person who has a good strategy will not be as successful as the PM who ships more stuff gets more reps and has the ability…”
Maggie Crowley · 10:30

#product management#strategy#shipping#career

Hot Take27:30

Carrying the Water: When in Doubt, It's Your Job

Maggie's third trait of great PMs has 'no tips and tricks — just do the work.' If you catch yourself saying 'that's not my job,' that's probably exactly what you should do. Because a PM owns the outcome, no one else is incentivized to fill the gaps — you have to hop on the sales call, do QA, write copy, whatever it takes to make the product succeed.

'That's not my job' is a signal you should do the thing
PMs own the business result, so they must fill every gap
Engineers and designers can finish and hand off; PMs can't
Doing the unglamorous work is what makes the product succeed

“if you ever find yourself saying something like that's not my job that's probably a thing you should do”
Maggie Crowley · 27:30

#product management#ownership#work ethic

Hot Take58:30

Bragging About Being 'Data Driven' Is a Red Flag

Maggie's contrarian take: when a team or executive is loudly proud of being 'data driven,' it often signals they over-index on quantitative dashboards at the expense of qualitative judgment and real user research. You still need to instrument the product, but data can't tell you why things happen — and for most PMs, talking to ten users beats any dashboard.

Loud 'data driven' pride can mean neglect of qualitative insight
Dashboards tell you what is happening, never why
Managing via dashboard skips understanding the actual humans
For most products, ten user conversations beat the metrics

“people who are really excited about being data driven to me that is often times a red flag for their product thinking”
Maggie Crowley · 58:30

“most PMS most jobs most products you're going to be better off talking to 10 users and you'll get more and better insights out of…”
Maggie Crowley · 59:30

#data#user research#contrarian#product thinking

Hot Take1:01:00

Why Product Content Can Get in the Way of Real Impact

Maggie warns that polished frameworks online can trick people into thinking the framework is the point, when the point is impact. The best PMs have many frameworks, apply them situationally, and sometimes throw them all out and act on intuition. Content also boomerangs — as a published leader, people quote your old takes back at you when reality is more complicated.

Content must be sanitized and 'frameworkized' to be shareable
People start optimizing for the framework instead of impact
The best PMs discard frameworks when none fit the moment
Your own published takes get used against you as a leader

“content sometimes can get in the way of the impact because you're trying to apply it and you think that the point is the framework…”
Maggie Crowley · 1:01:30

“the best PMS have built up so many different Frameworks and they can apply them in different ways then sometimes they throw them out”
Maggie Crowley · 1:01:30

#product content#frameworks#contrarian#impact

Story· 3

Story24:00

It Took Five Years to Feel Competent — the Case for Going Deep

Maggie traces her own path — Tripadvisor rotation, a startup where she realized she had no idea what she was doing, then nearly four years at Drift — and says it took about five years to feel she truly knew the job. Staying long enough to see two or three cycles of the same product taught her more than bouncing between companies, because she saw the consequences of her own decisions.

Getting genuinely good at PM took roughly five years
Shipping a lot over time is what builds real expertise
Staying at Drift ~4 years let her see products through multiple cycles
Seeing the consequences of your decisions is rare and valuable

“so that's five years until I really felt like I knew what I was doing and that's because you just it takes a long time…”
Maggie Crowley · 25:30

#career#product management#tenure#growth

Story55:30

Her Worst Product: A Rewrite That Took 2.5 Years — Never Do It

Maggie's worst-ever ship: a team decided to rewrite a core, founder-written part of the product. The engineer promised six months; it took two and a half years and still wasn't done, with people rotating in and out and everyone hating it. The causes — arrogance, skipping Discovery, no one-pager, no real technical or design research. Her blunt lesson: never do a side-by-side rewrite.

A promised 6-month rewrite took 2.5 years and still wasn't finished
Root causes: arrogance, skipped Discovery, no spec, no research
Deciding to rewrite an existing product is itself a red flag
She believes a good PM must have shipped something genuinely bad and admit it

“it didn't take six months it took two and a half years it still wasn't done”
Maggie Crowley · 56:30

“if anyone ever tells you to do a rewrite don't do it a side by side rewrite nope”
Maggie Crowley · 57:30

#failure#rewrites#product management#lessons

Story1:00:00

You Can Just Do the Obviously Better Thing

Early in her career at Tripadvisor, Maggie watched VP of Product Adam Medros interrupt someone over-justifying a project with numbers and say: if it's obviously, logically better, use your good judgment and just do it. The lesson stuck — sometimes you don't need more research or a dashboard to greenlight a clearly good idea.

Not every decision needs a mountain of supporting data
When something is logically better, good judgment is enough
Endless number-justifying can be a stalling tactic
'Just do the obviously better thing' is a card worth pulling

“if it's obviously better if it's logically better use your good judgment to do that thing”
Maggie Crowley · 1:00:30

#decision making#judgment#product management

Q&A· 1

Q&A31:30

How to Break Into PM — Just Get the Title Stamped Once

Asked how to break into product management, Maggie says the two most common paths are switching laterally inside a company or joining a startup — both hard. But the key unlock is getting the PM title on your resume at all: once you've had it once, hiring gets far easier, because managers screen out people who've never been a PM.

Two main entry paths: lateral move within a company or joining a startup
Hiring a first-time PM is a big lift for the manager, which is why it's rare
Once you have the PM title, everything downstream gets easier
The next screening question is always 'what have you shipped?'

“if you can get someone to stamp you with the product manager role take it because to your point it's what we screen on”
Maggie Crowley · 34:00

#career#breaking into pm#hiring

Tool· 2

Tool11:30

Read Your Writing Out Loud to Simplify It

A simplification trick Maggie learned from her dad in grade school: read whatever you wrote out loud. Half the time you'll immediately hear that it's too complicated or doesn't make sense, and it forces you toward the plain version of what you're trying to say.

Reading writing aloud exposes overcomplicated, unclear passages
Since much of PM work is written, this is a high-leverage habit
It's a simple, learnable tool rather than an innate talent

“when you write something read it out loud literally just read the thing you wrote”
Maggie Crowley · 11:30

“half the time you'll realize it's way too complicated doesn't make sense”
Maggie Crowley · 12:00

#writing#simplification#communication

Tool1:15:00

Maggie Crowley's Book Recommendations

In the lightning round, Maggie names three books she recommends most: The Presentation Secrets of Steve Jobs for improving speaking and getting distracted execs to agree, Thinking in Bets by Annie Duke (tying back to the theme of making bets), and Scaling People by Claire Hughes Johnson as a desk reference she keeps close as a manager.

Presentation Secrets of Steve Jobs — speaking and persuasion
Thinking in Bets by Annie Duke — decision-making under uncertainty
Scaling People by Claire Hughes Johnson — a manager's desk reference

“thinking in bets by Annie Duke is the second one”
Maggie Crowley · 1:15:30

#books#recommendations#management

Takeaway· 4

Takeaway12:00

Just Say the Thing — Write How You'd Explain It Out Loud

When people hand Maggie a convoluted document, she reads it, puts it down, and asks what they're trying to say — and their spoken answer is always clearer than the doc. Her advice: the sentence you'd say in conversation is the sentence you should write. Prose doesn't need to be formal; the goal is to get things done.

The plain spoken version is usually the correct written version
Documents don't need a formal, school-essay register
Ask 'what are you trying to say?' to find the real message

“the thing that you said to me in conversation is the thing you should write it”
Maggie Crowley · 12:30

#writing#communication#clarity

Takeaway08:00

Following Up on Results Is Rare — and It's How PMs Stand Out

Everyone names a metric they want to move; almost no one comes back later to report what actually happened. Maggie says that as a leader she constantly has to chase people for follow-up, so the PM who proactively returns and says 'here's what happened' stands out enormously. It's easy to do and disproportionately high value.

Most PMs set a target metric but never report the outcome
Leaders usually have to ask for follow-up — proactive PMs are rare
Put calendar reminders to check dashboards weeks and months out
Following up serves both visibility and your own learning

“I can't tell you how rare that is and how many times as a leader you might have to ask for that”
Maggie Crowley · 08:30

#product management#metrics#career#follow-up

Takeaway1:06:00

Writing Online Was the Best Thing She Did for Her Career

Maggie calls creating content the best thing she's done for her career. The benefits: networking and access to people she otherwise wouldn't reach, a personal brand that keeps her employable and pulls in self-selecting hires, and — her favorite — learning faster, because making content forces you to actually process and summarize what you did.

Content created networking and access she wouldn't have had
A personal brand keeps you employable and attracts aligned hires
Making content forces you to reflect on and process your work
That reflection is what made her a better product person faster

“it's probably the best thing I've ever done for my career”
Maggie Crowley · 1:06:00

“it's helped me learn more from the work I've done than I otherwise would have been able to because in order to make content you…”
Maggie Crowley · 1:07:30

#personal brand#content#career#writing

Takeaway1:09:00

How to Create Content Without Being Cringe

For people scared of seeming thirsty or cringey, Maggie's advice: accept that your first posts will be bad, and be genuinely authentic. Her podcast worked because the questions were real problems she faced in her own job. She cites an Einstein-ish line a guest shared — seek not to be successful but of value — as the right framing: share what's genuinely useful and interesting to you.

Your first 10-20 posts will be cringe — start anyway
Authenticity is non-negotiable; the content has to be real
Share only things you've actually done, or you'll run out fast
Aim to be of value, not to build a following

“step one is going to be cringe like your first 10 20 however many posts are going to be bad”
Maggie Crowley · 1:09:00

“seek not to be successful but of value”
Maggie Crowley · 1:11:00

#content creation#authenticity#personal brand

Key ideas

Frameworks in this episode

Ruthless Simplification for PM Writing

Start-With-Why One-Pager

The Data-Driven Red Flag

The Landscape-First Product Strategy Doc

The Three Threads of Great PMs

People & resources mentioned

People · 11

Resources · 41

Insights & moments

◆Hot Take· 4

Strategy Is Only 5% of the PM Job — Shippers Beat Strategists

Carrying the Water: When in Doubt, It's Your Job

Bragging About Being 'Data Driven' Is a Red Flag

Why Product Content Can Get in the Way of Real Impact

❝Story· 3

It Took Five Years to Feel Competent — the Case for Going Deep

Her Worst Product: A Rewrite That Took 2.5 Years — Never Do It

You Can Just Do the Obviously Better Thing

?Q&A· 1

How to Break Into PM — Just Get the Title Stamped Once

✦Tool· 2

Read Your Writing Out Loud to Simplify It

Maggie Crowley's Book Recommendations

▲Takeaway· 4

Just Say the Thing — Write How You'd Explain It Out Loud

Following Up on Results Is Rare — and It's How PMs Stand Out

Writing Online Was the Best Thing She Did for Her Career

How to Create Content Without Being Cringe

Hot Take· 4

Story· 3

Q&A· 1

Tool· 2

Takeaway· 4