Insights

Product managers love their jargon; executives love results. When those two worlds collide, product management rarely wins—because leadership doesn’t fund vocabulary, they fund outcomes.

Whether you’re applying for a product leader role—or already carrying the title—there are questions worth asking that go far beyond interviews. These aren’t career-planning questions; they’re risk-assessment questions. The answers reveal whether you’re truly leading a product organization… or quietly contributing to the chaos. It is helpful to think of yourself as a free agent. You choose to play for this team. You can also choose to stop playing.

In my first product manager role, I started out entirely tactical. I became more strategic only after I stopped optimizing for sales requests and started truly understanding the market—its problems, friction, and outcomes, not just the sales team’s urgent needs.