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 — Brought to you by Productroadmap.ai—AI to connect your roadmaps to revenue: https://productroadmap.ai | Composer—the AI-powered trading platform: https://www.composer.trade/ | Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ Find the full transcript at: https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/ Where to find Maggie Crowley: • X: https://twitter.com/maggiecrowley • LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/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: 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: 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: 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/ • Strategy Doc Template: https://docs.google.com/document/d/1frggEj_gfFD4--8eNkkyY-zHryXbN5uIS8uiMDCYVes/edit • 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.