My boss frequently calls me aside for long private conversations about office politics. I'm unsure how to react

Question

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:

1. It seems inappropriate or unethical for him to instruct me on what to say in private meetings with other colleagues. Am I wrong?

2. 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?

3. If I am called to speak with his boss, should I stick to his script, or should I voice my own unfiltered opinion?

4. 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.

Answer 1

There are alot of dynamics described here and in general there are a number of approaches each with an increasing level of difficulty.

Summary:

1. Avoid the politics completely
2. Deflect the politics until you don't have to deal with them
3. Attempt to separate yourself from the politics
4. Learn to navigate the political waves without being sunk or sinking others.

Details:

1. Find another job with less politics that you can spin as career advancement by expanding your resume and working in something new.

2. If you stay, focus on the facts alone to form your stances and opinions. This includes strong boundary guideline understanding between responsible parties. If someone else is ultimately responsible, even if you are working on it for them, then ensure that other person answers the questions related to that by re-direction. There are alot of ways to say things without using direct verbiage. (i.e. bosses boss asks for a report or something: I reported that to my boss who was going to give that to you. I'm not sure but I think he was tweaking it for what you want instead of my raw output with extra stuff in there. I think he should answer your questions) If there is a direct question regarding your specific work, then you can just answer that honestly and inform your boss if there is an issue, that he asked a point blank question about x and I wasn't going to lie to him/her. This is a very good thing to master, but is also sometimes tough as the manager can easily change your responsibilities thus taking this avenue away completely.

3. Try to let your boss know that you really like to avoid politics and these political discussions are way more information than you are comfortable discussing. You can include that you really like just doing the "technical/detailed" parts and avoiding the "management/politics/conclusions" of the job field. This and number 2 usually work well together.

4. Learn to play the political game by reading people and their intentions and always word things a certain way as to make them feel good with your answers but not come off against either your boss or your bosses boss. This is much harder and takes lots of practice and interactions to get good at, but it does keep the peace and keep you out of the line of fire if you are able to do this.