No, you should not. And when I say that, I mean friends, not friendly.
Okay, I know there are people out there who are friends with their bosses, but I think, for the most part, it’s best to have a friendly relationship with your boss but not a true friendship.
Why? Because it can make things difficult and awkward. It could even potentially destroy the friendship! For example, what if you ask for a raise, permission to telework one day a week, or the opportunity to take the lead on a high profile project…but your request is denied. Unless you are able to accept the criticism you receive (“You haven’t performed to the level needed to merit a raise,” or “I would feel more comfortable having you in the office every day,” or “I think ‘so-and-so’ is in a better position to lead that project”) as coming from your boss and not your friend, it will probably be pretty hard to separate what your boss is telling you from what is coming out of your friend’s mouth.
On the other hand, what if your boss/friend doesn’t think you deserve to get a raise, work from home, or lead the project, but grants your request anyway out of loyalty and friendship? Well, it’s quite likely he/she will start to feel resentful towards you for having to go against his/her better judgement and granting the request because you are a friend.
And then there’s the problem of stepping out-of-line. When you’re friends with your boss, you may find yourself voicing your opinion or doing something in a way you would do so with a friend but which may be totally inappropriate to do with a boss. And that is not a road you want to travel! I speak from personal experience!
A long, long, long time ago I worked in a criminal defense law firm as a paralegal. The senior partner often paired me up with the new attorneys so I could teach them how to navigate through the system and how things worked and got done. I ended up working for several months with one of the new attorneys, Scott, who became a pretty good friend.
One of our clients had been charged with drug possession and wanted to go to trial. Scott was convinced he could win the case. Based on my experience with dozens of similar cases, I believed there was no way this guy was going to win the trial and I told Scott he should take the prosecutor’s plea bargain (which, I remember clearly, was to have the charge dropped to a misdemeanor and pay a fine since it was a first offense).
Long story short, Scott took the case to trial, lost, and the client got jail time, a felony on his record, and community service. When Scott came back to the office and told me, I threw a fit. I yelled at him (well, I didn’t really yell…just spoke really, really loudly so everyone in the surrounding offices could hear). I told him he should have listened to me and that he made it worse for the client. Basically, I was totally out-of-line. Scott was the attorney and it was his call to make. And that was pretty much the end of that friendship.
So, when you start a new job and realize you have a fantastic boss who you could easily see becoming a good friend, you might want to think about whether or not the friendship could survive the workplace.