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.n