Tip
Brandon Chu talks about prioritizing decisions as a PM: focus relentlessly on the few truly critical decisions, and trust your gut on everything else. But here’s the insight he adds: “Once you’ve had a few battle scars of things that you thought were going to ruin everything, your career, your reputation, blah, blah, blah, and then actually nothing happened, you just start to raise the bar about what’s actually important.”
Turns out AI adoption crises work the same way.
Your team wants to implement AI agents that will interact directly with customers. No review loop, autonomous decisions. Your VP of Operations says this will destroy customer trust if it hallucinates. Your head of compliance says we’re exposed to massive regulatory risk. Everyone’s escalating. This feels like a career-defining decision.
Except you’ve been through this movie before. You remember when your company was “betting the business” on mobile and people said the mobile web would never work for complex workflows. You remember when cloud migration was going to create unacceptable security risks. You remember when remote work was going to destroy company culture. Each time, the sky was falling. Each time, you figured it out.
That calibration—knowing which crises are real versus which just feel urgent—comes from living through enough “career-ending” decisions that turned out fine. Younger managers treat every AI decision like it’s existential because they haven’t accumulated the scar tissue yet. You have. You’ve seen enough false alarms to recognize the pattern.
This doesn’t mean ignore the risk. It means you can evaluate it calmly instead of letting fear drive the decision. You know the difference between “this could end badly if we’re careless” and “this will end badly no matter what.” That judgment only comes from weathering enough storms.
Context
Brandon Chu is VP of Product at Shopify where he’s worked for seven years through hypergrowth (500 to 12,000+ people). His framework for decision prioritization emphasizes spending time only on truly critical decisions, but the meta-skill is knowing which decisions are actually critical.
That calibration develops from experiencing enough “disasters” that weren’t—the project that seemed like it would tank your career but ended up fine, the bet that felt reckless but worked out. For experienced leaders, that pattern recognition is the advantage.