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

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.