The Journey of Dedication: Insights from a Small Sport Athlete

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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Brought to you by Productroadmap.ai—AI to connect your roadmaps to revenue | Composer—the AI-powered trading platform | Eppo—Run 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:

• X: https://twitter.com/maggiecrowley

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Maggie’s 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 your work

(19:39) Maggie’s 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 “carrying the water” 

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

(31:42) Advice on landing a PM role

(34:36) Maggie’s 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 as a career accelerator

(1:14:27) Closing thoughts

(1:15:17) Lightning round

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Referenced:

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

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

• Notion: https://www.notion.so/

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

• Drift: https://www.drift.com/

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

• Unpacking Amazon’s 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/

• 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/

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

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

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

• 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/

• Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_122232

• 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

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

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

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

• Future: https://www.future.co/

• Ladder: https://www.joinladder.com/

• Pump Log: https://pumplogapp.com/

• Huckleberry: https://huckleberrycare.com/

• Toast: https://pos.toasttab.com/

• Careers at Toast: https://careers.toasttab.com/homepage

• 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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