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 — 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.