Hilary Gridley: How to coach product teams to take a punch

When you feel criticized or misjudged, don’t argue the past or obsess over what others think. Ask: “What is one small thing I can do next that demonstrates the opposite of what I’m afraid this person thinks of me?” That shifts focus from ego and perception to agency and behavior.

Borrowed from CBT, behavioral activation says you don’t wait to feel motivated before acting; you take small, mood-lifting actions to break negative spirals. Hilary applies this both personally (a list of go-to actions) and managerially (helping reports identify specific, doable next steps when they’re stuck).

Hilary regularly debriefs her team on key meetings: what senior leaders said, how she interprets it, and what she’ll do differently. Over time this builds shared mental models (e.g., what the CEO means by “it must feel like the future”), reduces approval bottlenecks, and lets PMs act autonomously.

Instead of open-ended “What should I do?”, state your hypothesis and ask, “Do you agree?” or “Is that right?” This forces you to take a position, lets the other person correct your model, and rapidly calibrates your judgment—whether with legal, executives, or your own manager.

Your job isn’t to impose your internal vision on the CEO; it’s to deeply understand their vision and operationalize it as brilliantly as possible. Argue hard when you have a strong case, but if you lose the argument, shift into, “Assume they might be right—how do we now make this path succeed?”