Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

5 • 1.5K Ratings

🗓️ 5 November 2023

⏱️ 83 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.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://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 [email protected].

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Lenny may be an investor in the companies discussed.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe

Transcript

Click on a timestamp to play from that location

0:00.0	If you ever find yourself saying something like,
0:03.0	that's not my job, that's probably a thing you should do.
0:06.4	And you know what, it probably isn't your job.
0:08.4	And it probably is someone else's job,
0:10.3	and you can spend your life getting frustrated at that or you can just get over and get the work done.
0:14.0	And people who are willing to just get the work done
0:16.0	will move faster, their products will be more successful,
0:19.0	and they probably aren't carrying around all that anger and crappy emotion because as a
0:27.3	PM for better or for worse and maybe this is not how we all wanted to be but you're
0:31.6	oftentimes the emotional center of the team,
0:34.9	and it's your job to keep people motivated, keep people excited, keep them bought into the project,
0:40.2	and you just have to like keep that optimism going and it's hard work and part of it can be just like you know what let me take that on I'll do this thing
0:48.7	I'll hop on the sales call I'll implement this with the customer you just have to do whatever it takes.
0:54.3	Today my guest is Maggie Crowley.
0:59.4	Maggie is currently Vice President of Product at Toast.
1:02.7	Prior to this, she was VP and Head of Product at Charlie Health,
1:05.8	Senior Director of Product at Drift,
1:07.9	Director of Product at Bethspot,
1:09.7	a Product Manager at TripAdvisor.
1:11.6	She's also got an MBA from Harvard Business School. She was also an Olympic speed skater which is insane and incredibly cool. And in our conversation, we discuss the three most common threads across the best product managers that she's worked with, hired and managed,
1:25.0	how to very tactically write out a product strategy to share with your team and manager.
1:30.0	Why being data-driven is a red flag for product thinking, why product content you find online can be dangerous.
	...

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