My boss often calls me aside for long private conversations, usually outside the building or over the phone, where he lets me in on higher level discussions and "drama" taking place between him and his own boss. He expresses dissatisfaction with the way things are being handled at the company, using colorful language, and also gives me instructions for how to respond if asked questions by his boss so that we can "be on the same page."
I agree with many of his complaints (though not all), but in the interest of my own longevity at the company, I'm unsure whether I'm better served by agreeing with him in order to develop a strong relationship with my direct superior, or if this could end up causing problems for me in the long run.
Here are my concerns:
It seems inappropriate or unethical for him to instruct me on what to say in private meetings with other colleagues. Am I wrong?
Given his interest in having secret conversations, could what I say in response be used as justification for his own purposes in other conversations? I.e. what if my own words are being quoted behind my back?
If I am called to speak with his boss, should I stick to his script, or should I voice my own unfiltered opinion?
If my boss's dissatisfaction reaches a breaking point, and he quits or is terminated, will I be left in an awkward position?
So far, I have been politely concurring with most of his points or derailing the conversation by asking him questions that change the subject. But if this kind of "confidante" role persists for months or years, it would make me uncomfortable. I'm unsure if I should confront my boss and express my views about this, or if that would be counter-productive to my career prospects at the company?
As a side note, a family member who has been working as a business executive for decades has strongly urged me to directly confront my boss, but that prospect makes me nervous about spoiling the bond between me and the person responsible for my performance reviews. My boss often makes reference to the importance of these performance reviews.