Jorge Aboytes

As product people, we treat experience as our greatest asset. But the more senior we become, the more we lean on our own judgment as the deciding input, and that's exactly when judgment gets harder to question. AI has made this riskier than ever. It has never been easier to validate our assumptions straight back to ourselves: generate a persona that agrees with us, synthetic feedback that confirms the plan, a model that tells us what we hoped to hear. Confidence has gotten cheap, and disconfirming evidence has gotten easy to avoid.

This roundtable tackles a simple but uncomfortable question: how do Product leaders actually know when they're wrong? Rather than a presentation, it is a structured peer conversation. Jorge invites participants to share a moment they were most confident and most wrong: what they missed, why they missed it, and what signals they've since learned to watch for. The format is built for a senior room, where the real value lies in honest war stories rather than frameworks learned in a course.

Attendees leave with a sharper sense of how overconfidence actually forms, practical habits for seeking out evidence that breaks their own ideas instead of flattering them, and a shared language for naming the confidence trap when they see it on their own teams. The aim is for everyone to walk away with at least one concrete habit for catching their blind spots earlier.