As Patrick Harrington, a twenty-something business analyst, casually talks to his boss at a local bar, they begin to relate on a more personal level. Like two young kids beginning a friendship they joke about their plans for the impending zombie apocalypse. Suddenly Patrick’s boss goes quiet and pale. Did he say something wrong? Reflecting on this experience he blows out some smoke as he pulls away his cigarette from his mouth and lays it on the arm rest. “Talking about the large quantities of high power weapons and the ammo stockpile you own definitely raises concerns about the potential of a person going postal. Somewhat awkward for your boss to consider at a bar.”

Patrick’s innocent conversation turned into a serious faux pas. Everyone wants to be liked by his or her boss, but as the workplace begins to have more holiday parties, company picnics or after-work happy hours the straight line that divides our professional and personal selves starts to curve. Social media and the choice to be “friends” with our employers further blurs our vision of what we can and can’t share. As much as we are hyper aware of our behavior around our employer’s we want them to see who we are as people. What can or can’t you say to your boss?

WHAT NOT TO SAY:

As much as we want to share our life stories, no one needs to know every detail. Your health, for example, is personal. Brittany Sandhu, a manager of a textile company, was taken by surprise when an employee of hers began to speak about her UTI. “Rule of thumb,” says Sandhu, “Unless your ailment is going to effect you at work significantly or make you miss work for more than a day, your boss does not need to know about it!”

Juliano Laran, a respected marketing consultant, advises against talking about “what people accept or do not accept in their relationships (like what can your significant other do in terms of going out with friends, etc.). For older people, asking about why they have or do not have kids is also a forbidden topic.” Laran also commented that talking about your personal finances and what you can and cannot afford is also taboo. Tom Fields who works in finance stated “its usually better to steer clear of financial talks because then it comes off as you asking for a raise.” Talking about your coworkers may seem like a logical topic, especially since in our friend groups it is normal to talk about mutual friends. When speaking to a boss though talking about people you both know, in this case coworkers is a no-no. Cecilia Benvenuti, who has been working in the publishing industry for over 30 years said “whenever I have seen that happen, whether the comments were negative or positive it has always ended badly.”

WHAT YOU CAN SAY:

This one-on-one time is your chance to show your boss that you are more than a pencil pusher at the corner desk. You don’t have to go on about your philosophical views on hot button topics. Christian Garcia, executive director at Toppel Career Center, advises that “the conversation doesn’t have to be all about work; appropriate and safe conversations include sports, current industry events and trends, fitness and wellness, movies and tv, other hobbies, restaurants, etc.”

Garcia also recommends to use this time to pick your boss’s brain and ask for career advice. “Even better, get him or her to talk!” he claims. “Ask about his or her career and how they got to be where they currently are.” This type of conversation does two things: it let’s your boss know that you are truly interested in excelling in your field without promoting yourself and takes the pressure off you because they are the ones talking. Overall when talking to your boss even in an informal personal setting you should always remember that the relationship is still professional.

The juggling act gets more complicated when you throw social media into the mix. Social media is an online platform for us to express ourselves but when you have employers checking your wall or twitter feed all the sudden we have to think about filtering. For the most part it is still understood that even though you and your boss may be friendly, there is no need to be labeled “friends” on the internet.

 Paul Whiting a partner at an investment firm says “I would never establish a facebook relationship with a boss. That is what LinkedIn is for.” Emilia Lispi, who works as a student assistant at the dean’s office, had a more open view about social media interactions with your boss, “Personally, I don’t think it’s appropriate to be friends with your co-workers or boss on Facebook. Twitter is a little different because, generally, it’s a less personal and revealing site. If you keep your tweets clean and relevant to your field, it could be helpful for your boss to see that you’ve taken a personal interest in the business.”

If you are one of the unlucky folk who gets those pesky requests from your superiors there are a few things you should be aware of. One being that just because you are “friends” does not mean that you have to comment, like, retweet, or cyber-kiss-ass. Keep it minimal. Laran says that we have to be aware of our “social image” on these sites. We should be respectful but also use it as an opportunity to show more of who we are.

“While these sites are places to express ourselves, there is a fine line when you’re dealing with an employer/employee relationship,” says Garcia. “What if he or she saw a picture of you doing something questionable? Whether or not you agree that this should have a bearing on your work, the reality is that it might. You may also want to consider blocking certain content from your boss and/or co-workers just to be safe. Just remember: you have to work with your boss.”

Whenever confronted with the conundrum of being professional, it is best to be friendly but remember that you are not close friends. Treat your boss with the same gloves you would a guest at your parent’s house, be youself, make small talk and don’t talk about sex, politics or religion.

words_corinne nobili.  illustration_ashley brozic.