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

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Simplify and Prioritize: Focus on identifying the most critical task and stick with it. Avoid getting bogged down by multiple priorities.
Follow Up on Results: Always track and share the outcomes of your work. This builds trust and demonstrates accountability.
Carry the Water: Be willing to do the unglamorous work. If something needs to be done, step up and do it, even if it’s not technically your job.
Write Clear Strategies: Develop a comprehensive product strategy document that aligns with the company’s mission and goals. Share it openly with your team.
Create One-Pagers: Use concise one-pager documents to define the problem, why it matters, and the proposed solution. This helps keep the team aligned.
Build a Support Network: Create a small group of peers to review and provide feedback on your work. This can help you improve and stay focused.
Stay Resilient: Product management is hard work. Stay optimistic, motivated, and ready to take on challenges.

Maggie Crowley is the VP of Product at Toast, with prior experience at Drift, TripAdvisor, and Charlie Health.
She emphasizes the importance of taking ownership and doing whatever it takes to get the job done, even if it’s not technically your role.
As a PM, you are often the emotional center of the team, responsible for keeping everyone motivated and optimistic.

Simplifying and Prioritizing: The best PMs can break down complex problems and focus on the most critical task. They avoid getting distracted by multiple priorities.
Following Up on Results: Great PMs track the outcomes of their work and share results with stakeholders. This demonstrates accountability and helps build trust.
Carrying the Water: Successful PMs are willing to do the unglamorous work, such as customer support, sales, or writing copy. They take responsibility for outcomes, even if it means stepping outside their usual role.

While strategy is important, it’s only about 5% of a PM’s work. The real focus should be on execution, shipping products, and creating impact.
Impact is achieved by shipping more products, learning from each release, and iterating based on feedback.

Write Clearly: Read your work out loud to ensure it’s simple and easy to understand. Avoid overcomplicating documents.
Use Tools: Apply principles like the Minto Pyramid (start with the conclusion) and the rule of three (limit priorities to three items).
Seek Feedback: Have peers review your work and help you simplify it. Maggie has a Slack group with other product leaders where they share and critique each other’s work.

Set reminders to check on the outcomes of your work weeks or months after launch. Share these results with your team and stakeholders.
Following up not only helps you learn but also demonstrates your accountability and reliability as a PM.

PMs must be willing to do the hard, unglamorous work, such as customer support, sales calls, or project management. TAKE NOTE
This willingness to step up and take responsibility is what sets great PMs apart and leads to successful products.

Start with the Mission: Align your strategy with the company’s mission and goals.
Analyze the Landscape: Include a SWOT analysis, competitive analysis, and key risks.
Assess the Current State: Provide an honest assessment of your product’s current state, including technical hurdles and customer feedback.
Identify Opportunities: Based on your analysis, identify the top opportunities for your team.
Propose a Plan: Outline a clear plan with actionable steps and share it with your team for feedback.

A one-pager should include:
- Background and Context: What is the problem and why does it matter?
- Why Now: Why is this problem worth solving now?
- Proposed Solution: What are you going to do to solve the problem?
- Next Steps: Outline the plan for execution.
This document serves as a home base for decisions and keeps the team aligned.

Maggie has a small Slack group with two other product leaders where they share and critique each other’s work.
Having a peer group for feedback and support is invaluable, especially as you advance in your career.

Many PMs and leaders make up their processes as they go. The frameworks and strategies discussed are ideal versions, but real-world product management is often messy and unpredictable.
Maggie emphasizes the importance of staying flexible and adapting to challenges as they arise.

While not explicitly mentioned, Maggie’s advice on simplification and prioritization suggests that overcomplicating products or strategies can lead to failure. The key is to focus on what truly matters and avoid getting distracted by less important tasks.