Interesting post. You dive into a subject that covers common occurrences in the workplace. One big issue in workplaces I've observed (I'm a Recruiter and Career Coach) is getting along on a personal level with the boss is almost mandatory these days--especially in smaller companies. I think it can go both ways.
The best advice I give clients is to ask about work culture in interviews. I have worked with companies that have a happy hour in the office at 3 pm every Friday. For someone like myself, I'd love to work in a place like that. For others, it can be a little awkward and let you said, not productive for your career.