Has a user ever told you your product was too easy, and meant it as a complaint?
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We simplified a setup flow that used to take about ten minutes of configuration. Fewer options, fewer decisions, faster to the first result. A group of experienced users pushed back hard. They said the product now felt like it didn't trust them that the old settings were how they'd made it fit their actual job and that "simple" meant "generic." We'd optimized for the person starting and accidentally made the product worse for the person staying. The simplification was real but so was their loss. How do you decide when to simplify for new users without stripping away the control that keeps the experienced ones around?
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