“If were to ask a raise from your boss, describe the social context that your share with him/her,” I told my business communication class a few weeks ago. One student said that his best case scenario would be that he is friends with the boss. Probably 90+ of them raised their hands when asked if they shared the same opinion. Yeah, ever thought about befriending your boss?

Perhaps every worker would want to be on his or her boss’ good side. And why not? It’s a real advantage. If you already are, then you can only enjoy the status. But if you aren’t but thinking about befriending your boss, then better give it some thought. Let’s take a look at the different sides of things.

There’s nothing really wrong to be friends with your boss especially if you can both keep things isolated. You take professional matters as they are and so do you with personal matters. One advantage of being friends on the professional side of things is that, it totally creates a better line of clear and honest communication. You probably wouldn’t get that I’m-about-to-wet-my-pants feeling when the boss asks for you. Friendship also entails, trust giving you an advantage in things like promotions.

However, if you aren’t friends with your boss now. How can you be one.

Engage the boss through small talk. Take opportunity in those casual encounters – right after meetings, the company party, chit-chat at the water cooler… Look for common interests and engage him/her in a conversation about these. Avoid work related talk. This only emphasizes on your roles inside the organization. Thus, you don’t have to spy on your boss just to get those details.

Manage your A-game. Diligent employees always get to the boss’ good side and it’s always good way to start. So be sure to be do a more than just your barely-scraping by work. But be sure to manage your A-game. Too much effort and you may come off as a suck-up. Hey, given a sustained exceptional performance your boss may not even be your boss for long.

Don’t let things to get too personal. Sure, operating on a less professional level is a direction often taken by boss-worker friendships but one thing that you should avoid is being a tad too friendly with the boss. Try to back off a bit when you start to become an ear to listen and a shoulder to cry on. Being exposed to your boss’ vulnerability may 1) affect how you view your boss and 2) your boss may never just view you as a mere subordinate (meaning he/she might expect that you’d turn to his/her personal yes-man). Same on your case, never let your boss know your dirt.