Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, TripAdvisor)

Maggie Crowley is VP of product at Toast and previously vice president and head of product at Charlie Health, senior director of product management at Drift, and a PM at TripAdvisor. She’s also the host of Build, a podcast dedicated to product and product management. In today’s conversation, Maggie shares:
• The value of building a broad-based PM skill set
• Three qualities of the best product managers
• A step-by-step guide for crafting a product strategy
• How to break into PM
• Why great writing is often just simplifying your writing
• Why being too data-driven is a red flag
• The impact of content creation on Maggie’s career
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Find the full transcript at: www.lennyspodcast.com/masteri...
Where to find Maggie Crowley:
• X: / maggiecrowley
• LinkedIn: / maggie-crowley-42a97112
Where to find Lenny:
• Newsletter: www.lennysnewsletter.com
• X: / lennysan
• LinkedIn: / lennyrachitsky
In this episode, we cover:
(00:00) Maggie’s background
(04:06) Three common traits among the best PMs
(09:33) Strategy is an important but small part of the job
(11:14) How to get better at simplification
(15:13) Ownership
(17:53) Examples of simplifying your work
(19:39) Maggie’s Slack support group
(21:37) Following up on your work
(23:23) PM time horizon
(26:31) Staying in your role vs. trying a new opportunity
(27:37) The importance of “carrying the water”
(28:56) Pros and cons of the PM job
(31:42) Advice on landing a PM role
(34:36) Step-by-step process for writing your product strategy
(39:55) Not every feature needs a strategy
(46:29) The value of working through the process
(48:09) Maggie’s one-pager doc
(54:16) Contrarian corner
(55:44) The worst product Maggie ever shipped
(58:33) Why being “data-driven” is a red flag
(1:01:10) Content creation
(1:14:27) Closing thoughts
(1:15:17) Lightning round
Referenced:
• David Cancel on LinkedIn: / dcancel
• On Writing Well: The Classic Guide to Writing Nonfiction: www.amazon.com/Writing-Well-C...
• Notion: www.notion.so/
• The Minto Pyramid Principle and the SCR Framework: www.lennysnewsletter.com/p/mi...
• Drift: www.drift.com/
• Maggies Top 5 Product Lessons for 2021: www.drift.com/podcasts/build/...
• Unpacking Amazon’s unique ways of working | Bill Carr: www.lennyspodcast.com/unpacki...
• Inside Linear: Building with taste, craft, and focus | Karri Saarinen: www.lennyspodcast.com/inside-...
• Adam Medros on LinkedIn: / amedros
• Strategy Doc Template: docs.google.com/document/d/1f...
• How Figma builds product: www.lennysnewsletter.com/p/ho...
• Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: www.lennyspodcast.com/shreyas...
• Einstein quote: www.brainyquote.com/quotes/al...
• The Presentation Secrets of Steve Jobs: How to Be Insanely Great in Front of Any Audience: www.amazon.com/Presentation-S...
• Thinking in Bets: Making Smarter Decisions When You Dont Have All the Facts: www.amazon.com/Thinking-Bets-...
• Scaling People: Tactics for Management and Company Building: www.amazon.com/Scaling-People...
• Slow Horses on AppleTV+: tv.apple.com/us/show/slow-hor...
• Future: www.future.co/
• Ladder: www.joinladder.com/
• Pump Log: pumplogapp.com/
• Huckleberry: huckleberrycare.com/
• Toast: pos.toasttab.com/
• Careers at Toast: careers.toasttab.com/homepage
Production and marketing by penname.co/. For inquiries about sponsoring the podcast, email [e-mail].
Lenny may be an investor in the companies discussed.

[@maheshpatil1577]

A very rare interview/podcast where someone is talking what actually happens in Product Management rather than the typical bookish/theoretical/ideal scenarios. Liked it.

[@annabranquinho7638]

Loved this episode! Maggie makes it SO real. Totally agree that usually PMs will talk a lot about the theory, and less about the ACTUAL JOBS TO BE DONE. So valuable, thank you! I'm a PMM working toward becoming a PM. This was so insightful.

[@maggiecrowley2202]

Thank you!

[@nandana221]

This is one of my favorite episodes, I keep coming back to this. Thank you Lenny and Maggie

[@coolsush93]

Loved this podcast! Thanks Lenny for asking the right questions and thanks to Maggie for being real ❤

[@alexeyhimself]

As to 58:33: stop being "data-driven", start being "data-informed". Get quantitative data (what, who, when, how much), but use it to get qualitative data (why does this happen) to get the insights where to go next and why.

[@user-kg1od9es5d]

hate to break it to you, but this vague simple advice gets people NOWHERE.!

[@plvrzer]

maybe it’s just you that that advice doesn’t make sense, because it’s the right approach to use data to make better decisions

[@user-kg1od9es5d]

go ahead and apply it buddy - lets see what you actually achieve in reality.@@plvrzer

[@annabergevin1017]

Loved the strategy discussion (and template linked below). Also really appreciated the point about doing things that aren't your job; your job is to drive the outcome and often that means unsexy work, things falling through the cracks, etc. You have to play the long game of changing behavior, getting resource gaps filled, etc, but in the short term you just need to ship the thing so that means doing stuff that isn't your job. 👏

[@philmonty32]

Best video I have seen on being a PM - nicely done. Ties in nicely with Essentialism as a core business value.

[@HiroFerreira]

So real and human set of guidelines. Ease to relate, amazing! Thanks for the great chat!

[@WendyHernandez-sb4zk]

Thank you for this incredible collaboration!

[@hananyariv]

Great conversion from a real product leader. thank you both for the insightful time.

[@user-iq3ti1yh6c]

Great speaker, great material! THANK YOU!!!

[@balasubr2252]

Excellent advice and great conversation

[@tanushreebose828]

Lenny, I'm curious why this interview primarily focused on IC work. It seems like there was a missed opportunity to explore which skills she utilizes more or less frequently as a VP and people manager. For example, how does she approach coaching the people managers on her team and setting up her product org for efficiency?

[@jgonsalk]

She's awesome, would love to work for her. Totally agree with every point.

[@maggiecrowley2202]

Thanks so much!

[@jgonsalk]

@@maggiecrowley2202 Wow! I'm very excited to hear from you directly. Meant every word. I pretty much always write up an impact blog for every initiative. There was one that was stalled for a while because I haven't had time. Well, your words have inspired me to write some SQL and pull the numbers so I can close the loop on it. Keep sharing your awesome perspectives on PM, it's making an impact :)

[@atharvawankhede2085]

Liked points - " I write strategy documents for me." Its a way to know you have done the work (properly). And then just share it. - "What has to be true about the world for that to be true.?

[@user-kg1od9es5d]

the second part is stolen/refereneced word-for-word from someone else that she did not credit for their work on strategy.... if youre reading this, you know im right.

[@olemew]

@@user-kg1od9es5d what's the original source

[@alexeyhimself]

Lenny, do we have that 39:20 template from company's vision to an individual team's priority? I didn't find it in links. This is a very critical for Product Leaders to make this super clear for all the teams: guys, this is our company mission and vision, and these are business goals, and these are product vision, and these are product goals, and ... -- I've heard about it several times, but haven't yet seen that template to be shared by anyone yet. Would be nice to have it too. Thank you!

[@LennysPodcast]

Strategy Doc Template: docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit

[@maggiecrowley2202]

So glad it was helpful!

[@RamandeepSingh-qd3qz]

Lenny, please share the name of the book you used to improve your writing skills

[@LennysPodcast]

On Writing Well

[@jaysheelpradhan]

Could you share the template mentioned in the 39th min please

[@LennysPodcast]

docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit

[@jaysheelpradhan]

@@LennysPodcast Thanks so much 👍

[@eugene_dudnyk]

Simplification is reduction of nuance. Incompetent simplification is a disaster.

[@user-kg1od9es5d]

Pretty poor explanation of what a product strategy is for someone who is of VP level....

[@olemew]

what aspects did you miss or thought were not relevant? any interview you could link that did a better job?