When do you favor the experimenter vs. the safe bet in candidates? I saw many problems arising from shiny-object syndrome over the years when it comes to tech choices. But also sometimes reinventing a process made it more maintainable and simpler. Do you usually take this into account in interviews?

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I look at context more than labels. I favor experimenters when the role needs change, ambiguity, or building from scratch. I favor the safe bet when stability, scale, or risk control matters. In interviews, I care most about whether candidates can explain why they chose an approach and what tradeoffs they considered.

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This is a great take, people can be ambivalent, so when you choose to value a person which can understand what is needed and when you are definitely doing the right thing!

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