When friends become bosses

I recently made a comment about "that moment when a friend becomes a boss", which reminded a longtime reader of their situation. I'll call this reader "Charlie", and talk about their relationship with "Andy" and "Bob":

We are all scientists [redacted], and have been with the company for less than five years. We all reported to the same manager when [Andy] was hired in (they were recruited and befriended by Bob early on) which set us up as a peer group. Since then, our lab has since restructured such that Bob and I still report into a common boss, but now Andy reports into Bob.

Andy has noticed some changes in behavior in Bob. Bob has always liked to kid/tease, but the new power dynamic really screws with Andy's comfort level in engaging back thusly. Bob has also begun to come across as very patronizing when assisting or training Andy. I've noticed some pretty unsavory people management tactics being employed by Bob (ambush meetings, including performance review, for example), but I've tried to cut him some slack as a first-time manager.

I've pointed out to Andy these tactics employed by Bob and that he's likely intentionally using them to put himself at an advantage during meetings. I think at heart, Bob is a good guy and truly hope he's merely experiencing a learning curve as a new manager. As I'm still Bob's "peer" instead of "direct report", I'm trying to think of ways to use that status to directly or indirectly affect some change in the uncomfortable aspects of Andy and Bob's interpersonal dynamic.

I'd like to think that having a friend for a boss is a good thing. In general, bosses ideally should be helpful people in that they should equip you with tools and training to do your job. They should also have your best interests in mind, if not for benevolent reasons than at least because they're hitching their future onto yours and should be looking to develop and promote you as a way to promote themselves. I have a friendly relationship with my boss, but he's been my boss since day one. I think the truly sticky parts of this situation arise because of that transition from a "peer" friend to a "boss" friend and the associated change in the power dynamic. Power can change a person, some friends are undoubtedly going to be poor managers, and the situation is fraught with other quagmires that both parties (although probably more often the direct report) will have to learn to navigate. 

This is a rather wonderful case of serendipity, in that I was actually commenting on when one of your friends says something that makes it obvious that they have switched their mentality from "worker" to "boss." But then again, it got me this wonderful (?) dilemma, so who am I to argue?

I've been in Charlie's shoes, where I was acquaintances with "Danny", and then ultimately his direct report. That situation worked out, so far as I could tell, quite well. Even though Danny was younger than me, I felt that he was more experienced and quite a bit more emotionally mature than I was, especially with regards to our relationships to authority. If Danny had begun using odd management techniques like ambush meetings*, our relationship would have changed significantly.

I think that Charlie is being really smart in recognizing that Bob is a new manager and should be cut a little bit of slack in the beginning.

Here's my questions for the readers:

• Have you been in Andy's situation? 
• For those who have direct reports, have you ever been a Bob? How did you get better? 
• How long should Bob's shakedown period be? Should it be measured in months or years? 
• What is the best way for Charlie to influence Bob? 
• How friendly should you be with your boss? 

*I have been the recipient of one. It may have been deserved. It was not fun.