[CiPHPerCoder]

> - have some backbone eg, if your manager is wrong, tell them (in private!) but accept if they don’t agree, they have the final word.

Having some backbone and some tact is a good thing, but never showing backbone outside of "(in private!)" isn't always the right answer either.

I think it's better to learn to read the room and know when it is or isn't appropriate to raise your objections in a somewhat public manner.

Defaulting to privately when in doubt is a good strategy, but sometimes you have to call a spade a spade or the whole company suffers for it.

[eranation]

Yep. This is aimed more at the OPs target audience (people who are learning web development) and I think being the person to call everyone out might be correct technically but not politically on your first day as a junior web developer. As you said, it's all about reading the room. I would rephrase it though to - ask questions, such as "what would you do if x happens" or "did you consider y as an alternative" or "did you know that tool z exists and does all that stuff you are planning to build from scratch" vs sentences that end with a period. It should never be in the form of "you are wrong and I'm right because of (list of facts/opinions/doesn't really matter as the person probably stopped listening already)"

[lostcolony]

For most managers, one level of indirection higher.

"Is X possible?", "I like it, but are there any other possibilities?", "That sounds fun, but have we looked to see if there are any available tools that we could leverage", etc.

These are all the types of questions you'd expect a clueful manager to ask the people under him, but they actually work pretty well to guide a superior who thinks they have an answer, but you know it to be the wrong answer. They have to arrive at the new answer themselves, and implying that there is a better answer (such as 'did you know that a tool exists and does all the stuff you are planning') will cause them to be defensive. Let them work their way to the solution themselves, though, and they'll sing its praises for you.

[bjornlouser]

" ... ask questions, such as "what would you do if x happens" "

Yep. I already thought of everything.