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

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 | Composer—the AI-powered trading platform | Eppo—Run reliable, impactful experiments
—
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 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
—
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://w