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.