And that’s a feature, not a bug. [End of feature]
“I cried in the supply closet,” she says with a wince. “Then I wrote a post-mortem, automated the fix, and bought donuts for the on-call team.”
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? ncg kaylee
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.
“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.” And that’s a feature, not a bug
In an industry obsessed with experience, NCG Kaylee is proving that sometimes, the most valuable thing you can bring to the table is permission to forget what you’re “supposed” to know.
Her internal blog series, “Things I Was Too New to Know Not to Ask,” has become required reading for onboarding cohorts. She’s been informally dubbed the . And her manager, Derek, has changed his entire approach to mentorship. Within her first month, she documented “Kaylee’s First
“She asked for the org chart of failure ,” Derek recalls, laughing. “Not the official reporting structure. She wanted a map of who actually makes decisions when something breaks at 2 a.m.”