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“I don’t know how things ‘usually’ break,” Kaylee told me over a cafeteria oat milk latte. “So I just look at how they could break. Sometimes senior engineers have seen so many disasters that they’ve stopped imagining new ones.”
That post-mortem — titled “Oops, Did I Do That? (And How to Never Do It Again)” — has since been adapted as a template for the company’s entire incident-response training. Kaylee doesn’t know if she’ll stay in infrastructure. She doesn’t know if she wants to be a manager, a principal engineer, or something else entirely. But she does know one thing: the power of a beginner’s mind in a world of experts. ncg kaylee
That question — naive, impractical, and utterly brilliant — became Kaylee’s signature. Within her first month, she documented “Kaylee’s First 50 Questions,” a living Google Doc that catalogued every assumption her team had stopped questioning years ago. Why is this legacy service still running? Who owns that orphaned repository? Why do we approve this permission in three different systems? “I don’t know how things ‘usually’ break,” Kaylee