S2:E6 - Help Me Understand Why: How "Dumb Questions" Might Save Your Product...and Your Startup

In this episode of Practical Product Management, we sit down with our friend and former colleague Sam Zebarjadi—an incredible product leader who has worked across healthcare, big tech, and startups. We’ve both had the pleasure of working with Sam (though not at the same time), and this conversation was a real treat.

Together, we explore what it means to build products in highly regulated industries and how constraints like compliance and risk can actually fuel innovation. Sam shares practical insights on how to collaborate with legal and regulatory teams as partners, not blockers, and why so-called “dumb” questions are often the smartest ones to ask. We also talk about how to stay relevant in a rapidly changing product landscape, the importance of customer empathy, and what it really means to build tech that disappears into the background—especially in healthcare and fintech.

Key Takeaways

• Regulation Isn’t the Enemy of Innovation Sam flips the script on the typical tech vs. regulation narrative. Instead of viewing regulation as a blocker, the best product teams use it as a framework that forces better, more sustainable innovation.

• Ask Better Questions—Especially the Dumb Ones “Help me understand why…” can be the most powerful phrase in a PM’s toolbox. Dumb questions often reveal flawed assumptions or outdated procedures that are ripe for change.

• Tech Should Fade Into the Background In healthcare and fintech, user delight isn’t about flash—it's about making tech disappear so patients, providers, and users can do what they need to do. Familiarity and trust matter more than novelty.

• Great PMs Are Translators and Empaths Sam reminds us that PMs succeed when they deeply understand their customers, collaborate across domains, and sit in the hard stuff—whether it’s a compliance meeting or a 2am production outage.

Questions for PMs

1. Are you using regulation as a reason to say “no,” or a framework to ask “how might we”?

2. Where could you invite compliance, legal, or engineering in earlier as true partners?

3. Do you understand what your users actually need—or just what they say they want?

4. When was the last time you sat in the pain of your own platform or customer support experience?