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Most founders aren't difficult.

They're stubborn for a reason—the world is constantly trying to kill their idea, and stubbornness is how it survives.

But here's the tension I see over and over: Founders want to be challenged. They also believe conviction is what got them here. If you ignore either side of that equation, the relationship breaks down completely.

My job—whether as a CPO, GM, or advisor—is to hold both truths at once. Challenge the idea while respecting the conviction behind it. Push back on the approach while protecting the ambition that drives it.

That's not just product management. That's leadership.

And it requires something most people don't talk about: the ability to absorb a founder's doubt and uncertainty without becoming destabilized yourself. Because they can't always show that vulnerability to their team, their investors, or sometimes even themselves.

If you're a founder feeling this tension, you're not broken. You're just scaling—and yes, it's lonely. The people who can actually help you grow are rare. They need to be confident enough to challenge you and secure enough to handle your conviction without taking it personally. Ideally, they are someone who has seen these challenges before (rather than a peer going through them at the same time.)

It's one of the hardest relationships to get right in a company. But when it works? That's when things actually move.

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