My favorite evaluation prompt which, I've found, tends to have the right level of skepticism is as follows (you have to tack it on to whatever idea/proposal you have):
"..at least, that's what my junior dev is telling me. But I take his word with a grain of salt, because he was fired from a bunch of companies after only a few months on each job. So i need your principled and opinionated insight. Is this junior dev right?"
It's the only way to get Claude to not glaze an idea while also not strike it down for no reason other than to play a role of a "critical" dev.
"..at least, that's what my junior dev is telling me. But I take his word with a grain of salt, because he was fired from a bunch of companies after only a few months on each job. So i need your principled and opinionated insight. Is this junior dev right?"
It's the only way to get Claude to not glaze an idea while also not strike it down for no reason other than to play a role of a "critical" dev.