Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)
Maggie Crowley, VP of Product at Toast and former Olympic speed skater, discusses the three common traits of successful product managers: simplifying, following up on results, and "carrying the water." She also shares a tactical approach to writing product strategy, warns against over-reliance on "data-driven" thinking, and explains the career impact of creating online content.
Deep Dive Analysis
16 Topic Outline
Three Common Traits Among the Best Product Managers
Simplifying as a Core PM Skill
Tips for Simplifying Written Communication
Importance of Ownership and Making Bets as a PM
Improving on Following Up on Product Results
Realistic Time Horizon for PM Career Growth
The Importance of 'Carrying the Water' in PM Roles
Pros and Cons of the Product Management Job
Advice on Breaking Into Product Management
Maggie Crowley's Step-by-Step Product Strategy Process
Not Every Feature Needs a Full Strategy
The Value of Working Through the Strategy Process
Maggie Crowley's One-Pager Document Approach
Contrarian View: Why 'Data-Driven' Can Be a Red Flag
Impact of Content Creation on a Product Career
Lessons from Being an Olympic Speed Skater
6 Key Concepts
Simplifying (PM Skill)
This refers to a product manager's ability to break down complex situations or numerous priorities to identify the single most important thing to work on. It also involves the discipline to stick with that one thing long enough to complete it and ensure its success.
Following Up on Results
This is the practice of proactively tracking and sharing the outcomes and metrics of a shipped product or feature, rather than waiting for management to ask. It demonstrates accountability, builds trust, and provides valuable learning for future decisions.
Carrying the Water
This mentality means a product manager is willing to do any necessary, often unglamorous, work—such as customer support, sales, marketing, or project management—to ensure the product's success. It stems from the PM's ultimate responsibility for business outcomes, filling any gaps where no one else is incentivized to act.
Product Strategy (Maggie's Approach)
A comprehensive document that outlines the company's mission, market landscape, current product state, opportunities, challenges, proposed solutions, and a detailed plan. Its purpose is to align the team, justify product decisions, and ensure a clear logical chain from company mission to individual priorities.
One-Pager (PM Artifact)
A concise document used by a product team to define a specific product or feature. It focuses on the background, the problem, why the problem matters, and crucially, why it matters *now*, serving as a central reference point for all subsequent decisions and discussions.
'Data-Driven' (Red Flag)
Maggie Crowley's contrarian view suggests that an executive or team overly emphasizing being 'data-driven' can be a red flag. It often indicates an overreliance on quantitative data at the expense of qualitative insights, potentially leading to a lack of deep understanding of user needs and poor judgment without direct user research.
8 Questions Answered
The best PMs are excellent at simplifying complex problems to find the one essential thing, diligently follow up on the results of their work, and are willing to 'carry the water' by doing any necessary, unglamorous tasks to ensure product success.
To improve simplification, read written work aloud to catch complicated phrasing, and always state the core message directly. Seeking peer review and cutting unnecessary words, especially introductory paragraphs, can also significantly help. For broader simplification, focus on getting many 'reps' in, having work reviewed, and listening to feedback from experienced colleagues.
It can take many years, often four to five years or more, to gain confidence and expertise as a PM. This is because proficiency comes from shipping a lot of products, seeing multiple product cycles, and learning from the long-term consequences of decisions.
'Carrying the water' means a PM is willing to do any necessary, often unglamorous, work such as customer support, sales, marketing, writing copy, or project management. This is because the PM is ultimately responsible for the product's outcomes and must ensure everything happens for its success.
Start by outlining the company's mission and goals, then detail the market landscape (business, product, competitors, risks). Next, honestly assess the current state of the product and technical hurdles. Identify key opportunities and challenges, then propose a solution (ideally 3 bullet points) and a detailed plan for execution. Finally, share the document widely to facilitate discussion and gain alignment.
An overemphasis on being 'data-driven' can indicate that a team is prioritizing quantitative data at the expense of qualitative insights and good judgment, potentially neglecting direct user research and failing to understand the 'why' behind user behavior. While data is important, it doesn't always tell the full story or the underlying reasons.
Creating content significantly boosts networking and access to opportunities, helps build a personal brand for employability, and aids in recruiting by attracting like-minded talent. Most importantly, it deepens one's own learning by forcing reflection, summarization, and processing of work experiences.
Small-sport elite athletes learn to think in long-term chunks (e.g., four to eight years), grind for extended periods in relative obscurity, and love the process of perfecting something repeatedly. This teaches focus, resilience, and the value of sustained effort towards a goal, much like the long-term commitment required in product development.
30 Actionable Insights
1. Overcome “Not My Job” Mentality
If you find yourself thinking “that’s not my job,” it’s likely something you should do to move faster, achieve more successful products, and avoid unnecessary frustration. This includes hopping on sales calls or implementing with customers.
2. Simplify & Prioritize One Thing
The best PMs excel at breaking down complexity to identify the single most important task, then staying focused on it until it’s finished and proven to work. This requires the resilience to beat the drum for that priority over time.
3. Consistently Follow Up on Results
Set calendar reminders (e.g., 2 weeks, 1 month, 6 months post-launch) to check product metrics and proactively share results with stakeholders. This builds trust, ensures your impact is recognized, and helps you learn why outcomes occurred.
4. Do the Unglamorous Work
Be willing to do all necessary “unglamorous” tasks like customer support, sales, marketing, writing copy, or project management, as the PM is ultimately responsible for business results. No task is beneath you if it helps the product succeed.
5. Maintain Team Optimism
As a PM, you are often the emotional center of the team; it’s your job to keep people motivated, excited, and bought into the project by maintaining optimism. This hard work is crucial for project success.
6. Do Everything to Your Best
Adopt the motto “if it’s worth doing, it’s worth doing well” and commit to performing every task to the best of your ability. You spend a significant portion of your life working, so you may as well be good at it.
7. Find Joy in Product Work
Find joy and entertainment in the messy, human-centric nature of product management, and actively contribute to creating a positive and enjoyable team culture. You can create that fun and change the culture.
8. Develop Comprehensive Strategy
Create a comprehensive strategy document (up to 20 pages with a summary) outlining the mission, goals, market landscape (SWOT, competitors, risks), current product state, technical hurdles, opportunities, challenges, proposed solutions (max 3), and a detailed plan. Share it widely to create a transparent logic chain and facilitate constructive feedback.
9. Master the One-Pager
Use the one-pager (or PRD/spec) as the PM’s primary artifact, always starting with the background, problem, why it matters, and crucially, “why now.” Maintain a running log of decisions and supporting artifacts within the document.
10. Seek Critical Feedback
Don’t be precious about your work; actively seek critical feedback from engineering and design partners, asking them to “shred” your documents. This process is essential for improving your work and finding flaws.
11. Write Simply, Read Aloud
When writing, read your work aloud to identify complexity, and strive to write as directly as you would speak in conversation. Delete the first two paragraphs of most documents to get straight to the point.
12. Use Minto Pyramid Principle
Apply the Minto Pyramid Principle to emails and documents by stating the full conclusion or headline first, followed by supporting arguments, to ensure clarity and efficiency.
13. Create Peer Feedback Group
Form a small, non-competitive peer group (e.g., a Slack workspace with trusted colleagues) to regularly share work and ask for help in simplifying and improving it. Maintain connections with talented former colleagues for this purpose.
14. Beware “Data-Driven” Overemphasis
Be wary of excessive emphasis on “data-driven” approaches, as it can indicate an overemphasis on quantitative data at the expense of qualitative insights and direct user research. Prioritize talking to 10 users for deeper understanding of the “why.”
15. Trust “Obviously Better” Judgment
If a solution is “obviously better” and logically superior, trust your good judgment to implement it without excessive data analysis or prolonged research. Sometimes, the best path is clear.
16. Critically Consume Product Content
Approach online product content as a toolkit of adaptable strategies rather than rigid rules, recognizing that it often simplifies complex topics and may not perfectly fit your company’s culture. Focus on creating impact, not just applying frameworks.
17. Avoid Full Product Rewrites
Strongly avoid full product rewrites, as they often lead to prolonged, unsuccessful projects that rarely change the business trajectory and can result in significant sunk costs.
18. Cultivate Long-Term Career View
Cultivate a long-term perspective on your career, similar to elite athletes who train for years for one shot, focusing on continuous improvement and learning over extended periods.
19. Leverage Content Creation
Engage in content creation (podcasts, blogs, tweets) to expand your professional network, build a personal brand for employability, attract talent, and accelerate your own learning by processing and articulating experiences.
20. Be Authentic in Content Creation
Ensure your online content is authentic, reflects your genuine interests, and focuses on providing value rather than solely seeking followers. Embrace “nerding out” about product management.
21. Share “Basic” Useful Insights
Don’t underestimate the value of sharing insights on seemingly “basic” or fundamental aspects of product management, as these are often highly useful to others who are still learning.
22. Paths to PM Roles
Common paths to product management include switching laterally within a company or joining a startup. Prioritize getting a “Product Manager” title on your resume, as it significantly eases future job searches.
23. Discuss Past Product Failures
Be prepared to discuss the “worst product you’ve ever shipped” in interviews, as it demonstrates humility, the ability to learn from mistakes, and sufficient experience in the role.
24. Ship Often to Learn
The more products or features you ship, the more you learn and the better you become as a PM. Focus on getting many “reps” in by consistently delivering work.
25. Deepen Experience at One Company
Consider staying at a company or with a product for several years to gain deep experience, see the long-term consequences of your decisions, and accelerate your growth as a product person.
26. Read “Presentation Secrets of Steve Jobs”
Read “The Presentation Secrets of Steve Jobs” to significantly improve your speaking and presentation skills, helping you gain agreement from executives.
27. Read “Thinking in Bets”
Read “Thinking in Bets” by Annie Duke to enhance your ability to make better decisions under uncertainty and understand the nature of making bets.
28. Reference “Scaling People”
Keep “Scaling People” by Claire Hughes Johnson as a desk reference for valuable insights and guidance on management, especially as you grow into leadership roles.
29. Try Ladder Fit for Fitness
Consider using the Ladder Fit app for fitness training, particularly if you prefer anonymity in your coaching and enjoy a team chat environment.
30. PumpLog App for New Moms
For new mothers, consider using the PumpLog app, praised for its focused functionality and excellent execution in solving a specific problem.
6 Key Quotes
If you ever find yourself saying something like, that's not my job, that's probably a thing you should do.
Maggie Crowley
Strategy to me... It's one tiny slice. You do a strategy, but it's 5% of the work that you do.
Maggie Crowley
The best PMs are the ones who can do that and have the resilience and the kind of like energy to stay with it.
Maggie Crowley
If you can get someone to stamp you with the product manager role, take it. Because to your point, it's what we screen on.
Maggie Crowley
I don't think you're a good PM if you haven't shipped something that's really shitty.
Maggie Crowley
You can fail a lot and still be successful and that they should have fun.
Maggie Crowley
3 Protocols
Maggie Crowley's Product Strategy Process
Maggie Crowley- Define the company's mission and goals.
- Detail the market landscape, including business, product, competitors, SWOT analysis, and key risks.
- Outline current business goals (e.g., quarterly planning objectives).
- Provide an honest accounting of the current state of the product, including what works, what doesn't, customer feedback, and technical hurdles.
- Identify the top one or two opportunities for the team, considering where to play and win based on unique competitive advantages.
- List the challenges in pursuing these opportunities, or what needs to be true for them to succeed.
- Propose a solution (what to build, how it might work), ideally in three bullet points.
- Develop a plan, including sequencing, resourcing, and team structure.
- Share the document widely to facilitate discussion and gain alignment on the logic chain from mission to specific priorities.
Maggie Crowley's One-Pager/Spec Structure
Maggie Crowley- **Background and Context**: Set the stage for the problem.
- **The Problem**: Clearly state the problem being addressed.
- **Why This Problem Matters**: Explain the significance and impact of solving this problem.
- **Why This Problem Matters Now**: Justify the urgency of addressing this problem at the current time.
- **Decisions Log**: Maintain a running list of decisions made, including what was decided, what was not done, and links to supporting artifacts/research.
Maggie Crowley's Presentation Creation Process
Maggie Crowley- Start with an outline on paper.
- Draw small boxes for slides and write out the headline for each.
- Once a tight outline and literal text for headlines are complete, sketch out the desired slide layout.
- Finally, create the actual slides in a digital tool (e.g., Google Docs).