In this episode of Practical Product Management, hosts Leah Farmer and Marilyn McDonald are joined by Steve Brieloff, a seasoned product leader from Expedia Group, for a conversation about what truly defines great product management.

Steve shares insights from his years leading teams across Expedia’s product suite, highlighting how getting the fundamentals right—from crafting precise problem statements to choosing meaningful success metrics—sets the foundation for success. The trio dives deep into the importance of language, the evolution of confidence and conviction in product decisions, and how bravery shows up at every level of a PM’s career.

From building trust through vulnerability to balancing open debate with decisive action, this episode explores how mastering the basics and leading with courage can transform teams, culture, and products alike.

Key Takeaways

1. Master the Fundamentals — and the Words You Choose Matter. Great product work starts with writing a precise problem statement and choosing the right success metrics. One misplaced word can send a team in the wrong direction.

2. Bravery is a Core Product Skill. Whether it’s voicing dissent, standing behind a decision, or leading culture change, bravery shows up at every level of product work — from junior PMs to execs.

3. Build Trust Through Vulnerability and Debate. Encourage disagreement, listen deeply, and be transparent — but also know when the debate is over. Leadership is about hearing others, making the call, and moving forward together.

In this episode of Practical Product Management, Leah and Marilyn sit down with Ali Rakhimov, Senior Product Leader, fintech founder, and author of Make Pigs Fly. Ali shares his unconventional path into product management as a self-taught immigrant, the lessons learned from scaling fintech for underserved schools, and leading $10M+ initiatives at Macy’s and T-Mobile.

The conversation ranges from the value of asking “stupid” questions in technical meetings, to translating empathy into reliable systems, to the balance between directness and tact in communication. Ali also draws parallels between raising four kids and managing teams—emphasizing adaptability, humility, and listening as core product skills.

Key Takeaways

1. Curiosity over credibility: Asking the “stupid” questions is often how you uncover blind spots, learn fast, and earn trust.
2. Empathy into action: Observing real users and solving their core problems matters more than shipping flashy features.
3. Adaptability is leadership: Whether managing teams or parenting, effective product leaders flex their style to the audience and context.

In this episode of Practical Product Management, hosts Leah Farmer and Marilyn McDonald welcome back returning guests Alesha Cronie and Geno White for a candid conversation about iteration. Together, they unpack why iteration is more than a process—it’s a mindset centered on learning, courage, and embracing discomfort.

The discussion explores the “courage gap” that often holds organizations back, the tension between incentives and innovation, and why MVPs so often miss the mark. The group also debates the evolving balance of product and engineering roles in the age of AI, and the importance of curiosity in solving real customer problems. It’s a lively and unfiltered look at what it truly means to “fuck around and find out” in product development.

Key Takeaways

1. Iteration is about learning, not perfection – moving fast matters less than learning fast, and that requires comfort with uncertainty.
2. Courage and trust are critical – organizations often get stuck not because the data isn’t there, but because leaders lack the courage to pivot or empower teams.
3. MVPs are often meaningless – reframing them as learning vehicles (or prototypes) keeps teams focused on outcomes instead of excuses.