Podcasts Technology Lenny's Podcast: Product | Growth | Career Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

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

Published: Nov. 5, 2023, 12:01 p.m.

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\u2019s also the host of Build, a podcast dedicated to product and product management.\xa0In today\u2019s conversation, Maggie shares:

\u2022 The value of building a broad-based PM skill set

\u2022 Three qualities of the best product managers

\u2022 A step-by-step guide for crafting a product strategy

\u2022 How to break into PM

\u2022 Why great writing is often just simplifying your writing

\u2022 Why being too data-driven is a red flag

\u2022 The impact of content creation on Maggie\u2019s career

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Brought to you by Productroadmap.ai\u2014AI to connect your roadmaps to revenue | Composer\u2014the AI-powered trading platform | Eppo\u2014Run reliable, impactful experiments

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Find the full transcript at: https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/

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Where to find Maggie Crowley:

\u2022 X: https://twitter.com/maggiecrowley

\u2022 LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Maggie\u2019s background

(04:06) Three common traits among the best product managers

(09:33) Strategy is an important but small part of the job

(11:14) How to get better at simplification

(13:39) Tips on simplifying your writing

(15:13) Ownership as a PM

(17:53) Examples of simplifying\xa0your work

(19:39) Maggie\u2019s Slack support group

(21:37) How to improve on following up on your work

(23:23) A realistic time horizon for PMs

(26:31) Staying in your role vs. trying a new opportunity

(27:37) The importance of \u201ccarrying the water\u201d\xa0

(28:56) Pros and cons of the PM job

(31:42) Advice on landing a PM role

(34:36) Maggie\u2019s 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\u2019s one-pager doc\xa0

(54:16) Contrarian corner

(55:44) The worst product Maggie ever shipped

(58:33) Why being \u201cdata-driven\u201d is a red flag

(1:01:10) Content creation as a career accelerator

(1:14:27) Closing thoughts

(1:15:17) Lightning round

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Referenced:

\u2022 David Cancel on LinkedIn: https://www.linkedin.com/in/dcancel/

\u2022 On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548

\u2022 Notion: https://www.notion.so/

\u2022 The Minto Pyramid Principle and the SCR Framework: https://www.lennysnewsletter.com/p/minto-pyramid-principle-scr

\u2022 Drift: https://www.drift.com/

\u2022 Maggies Top 5 Product Lessons for 2021: https://www.drift.com/podcasts/build/?wchannelid=hg0p3zf4yx&wmediaid=nxrdvmotr3

\u2022 Unpacking Amazon\u2019s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/

\u2022 Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO): https://www.lennyspodcast.com/inside-linear-building-with-taste-craft-and-focus-karri-saarinen-co-founder-designer-ceo/

\u2022 Adam Medros on LinkedIn: https://www.linkedin.com/in/amedros/

\u2022 How Figma builds product: https://www.lennysnewsletter.com/p/how-figma-builds-product

\u2022 Strategy Document Template: https://docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit

\u2022 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: https://www.lennyspodcast.com/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/

\u2022 Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_122232

\u2022 The Presentation Secrets of Steve Jobs: How to Be Insanely Great in Front of Any Audience: https://www.amazon.com/Presentation-Secrets-Steve-Jobs-Insanely/dp/0071636080

\u2022 Thinking in Bets: Making Smarter Decisions When You Dont Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216371

\u2022 Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/r

\u2022 Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o

\u2022 Future: https://www.future.co/

\u2022 Ladder: https://www.joinladder.com/

\u2022 Pump Log: https://pumplogapp.com/

\u2022 Huckleberry: https://huckleberrycare.com/

\u2022 Toast: https://pos.toasttab.com/

\u2022 Careers at Toast: https://careers.toasttab.com/homepage

\u2022 What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mess/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.



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