I have similar concerns, although I'm shocked the quoted question is where someone would draw the line. That in particular does not seem at all personal, or potentially damaging at all (if an employer regards an employee trying to gauge their value negatively they're probably a shitty company to work for anyway). Personally I wonder how effective any kind of general career advice could be without conferring with a level of intimacy I'd reserve for a therapist or close friend. I feel like only the most practical career advice (which is widely and freely available) could be offered up without delving into things like long term goals and personal motivations. I guess I could see this being useful if you have a well formed idea of where you want to go in your career and have trouble getting from point A to point B, or could use a little encouragement/social pressure, but I think the harder problem is figuring out that destination not the implementation details.
To both points: trust is earned over time and we have to actually design our onboarding flows and coaching processes around that idea. It's tricky, but it's how it should work -- we don't expect people to have implicit faith in any system, and actively coach them to question the world around them.
More people question too little than too much, so it's great to see you all are the opposite. :)
