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Maggie Crowley

Episode #188

Vice President of Product

Toast

🚀Career & Leadership🎯Product Strategy⚡Execution

📝Full Transcript

17,062 words
Maggie Crowley (00:00:00): If you ever find yourself saying something like, that's not my job, that's probably a thing you should do. And you know what? It probably isn't your job and it probably is someone else's job and you can spend your life getting frustrated at that or you can just get over and get the work done. And people who are willing to just get the work done will move faster. Their products will be more successful and they probably aren't carrying around all that anger and crappy emotion because as a PM, for better or for worse, and maybe this is not how we all want it to be, but you're oftentimes the emotional center of the team and it's your job to keep people motivated, keep people excited, keep them bought into the project, and you just have to 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. I'll hop on this sales call, I'll implement this with the customer. You just have to do whatever it takes. Lenny (00:00:57): Today my guest is Maggie Crowley. Maggie is currently vice president of Product at Toast. Prior to this, she was VP and head of product at Charlie Health, senior director of product at Drift, director of product at BevSpot, a product manager at TripAdvisor. 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 how to very tactically write out a product strategy to share with your team and manager why being data-driven is a red flag for product thinking. Why product content you find online can be dangerous. Her best advice for how to break into product management. Also, the impact writing online has had on her career and so much more. Maggie is amazing. (00:01:44): I'm excited for you to learn from her like I did. With that, I bring you Maggie Cr...

💡 Key Takeaways

  • 1Great PMs simplify complexity: find the one thing that matters and stick with it.
  • 2Follow up on results: check metrics 2 weeks, 1 month, and 6 months post-launch.
  • 3"Carry the water": PMs must do the unglamorous work (QA, support, sales calls) to fill gaps.
  • 4A product strategy doc is primarily for the PM to ensure their own logic is sound.
  • 5When writing specs/PRDs, the most important question is "Why does this matter NOW?"
  • 6Being overly "data-driven" can be a red flag for a lack of product intuition.
  • 7Avoid rewrites/redesigns; they almost always take longer than expected and fail.

📚Methodologies (3)

🚀 Career & Leadership

Three specific behaviors that define top-tier PMs: the ability to cut through noise to find the single priority, the discipline to close the loop on outcomes, and the willingness to do whatever unglamorous work is needed to ship.

Core Principles

  • 1.Simplify relentlessly: Identify the single most important task amidst chaos and stick to it until completion.
  • 2.Follow up on results: Set calendar reminders (2 weeks, 1 month, 6 months) to check if the feature actually moved the metric, and report back.
  • 3.Carry the water: Adopt a "no job is beneath me" attitude. Do QA, write copy, hop on sales calls, or manage projects if that's what is needed to ship.

"If you ever find yourself saying something like, 'that's not my job,' that's probably a thing you should do."

#high-performance#triad#career
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🎯 Product Strategy

A comprehensive document structure that forces the PM to rigorously assess the landscape and internal state before proposing solutions. It serves as 'homework' for the PM to ensure they aren't missing critical context.

Core Principles

  • 1.Landscape & Context: Mission, goals, competitive SWOT, and market POV.
  • 2.Honest Accounting: What is the brutal truth about the current product state? User feedback, tech debt, and what isn't working.
  • 3.Opportunity & Logic: Where can we win? What must be true for this to work? Then, and only then, propose the solution (max 3 bullets) and plan.
  • +1 more...

"I put in... an honest accounting of the current state of your product... What works, what doesn't work? What are your customers saying? ... What are your technical hurdles?"

#'honest#accounting'#strategy
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The 'Why Now' One-Pager

by Maggie Crowley

⚡ Execution

A simplified spec document that prioritizes the context and timing over the feature list. It centers the team around the problem rather than the solution details.

Core Principles

  • 1.Start with Context: Define the background clearly.
  • 2.The Two Critical Whys: Explicitly answer 'Why does this problem matter?' AND 'Why does it matter NOW?' (Urgency).
  • 3.Record Decisions: Use the doc to log decisions made and what is strictly out of scope.
  • +1 more...

"What is the problem, why does it matter, and why does it matter now?"

#one-pager#execution#process
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