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 transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT.
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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
• 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.