I've faced this a lot while working with LLMs in order to develop an architecturally sound spec; especially when I am learning a new language/framework where I am not intimately aware of what the best practices in that framework are. Are there some methods you're aware of to make LLMs less subservient and more confident in their approach?

Right, and my point is you have to ask objective pointed questions. For example, even "what do you think is best in this case, a database or keep it all in memory?" Best for whom? To what end? Easiest to maintain? Most resilient? Etc.