Career

The Pros And Cons Of Being Besties With Your Boss

Work mates, what would we do without them? Seriously – they save us from having to dine solo at lunch, are always there to indulge our incessant smack talk and honestly, just make the days go a whole lot smoother. How about buddying up with your boss though? Yeah, being chummy with your supervisor might make work life easier when gunning for that early Friday arvo knock off, but at times, it can get a little awkward.

If your work buddy has just received a promotion, or you and your current boss are starting to hit it off, here’s all you need to know: with the pros and cons of being besties with your boss.

PRO: You’ll be blessed with benefits

The inherent fear of your boss not liking you is one of the most common workplace worries – we’ve all been there, so it’s no wonder people are buddying up with their superior in the chance of developing a friendship. A friendship that can often come with a bunch of hidden perks I might add.

Your boss sees you as more than an employee, you guys are friends, so when it comes to stuff like promotions, time off and shift changes you’re likely to be favoured – friends like seeing other friends succeed!

Not only will you be on top of the list for work perks, but the ability to speak as freely as you like with your boss, deprived of boundaries can make for a much easier time when negotiating and partaking in general work chat – this is bound to make for a much cruisier work life.

CON: It restricts constructive criticism

If over the weekend you and your boss were busy sinking beers and hanging out, so it makes sense that come Monday, talking business can feel a little awkward. When the lines are blurred between your professional work relationship and friendship, things like criticism can be a little cringe-worthy.

The role of a boss is to manage, lead and dish out the constructive criticism when it’s needed, and hopping between the roles of boss and bestie can prove difficult at times.

Your feelings might be spared when it comes to work chat, and while this is a nice gesture, it deprives you from getting better at your job. Alternatively, if your boss does offer you some critiques, it can be sometimes difficult or annoying hearing it from someone you consider a friend – it’s important to remember that above everything else, they’re your boss, and it’s their job. 

PRO: It might make you better at your job

You’ve been spending all this extra time around your boss, so surely you’ve picked up on some inside info that could make you even better at your job. If you can, try and gage exactly what he or she is looking for in terms of quality of work, as well as what their schedule is like, you’re on to a winner.

For example, if you’re in a rush and need items approved pronto, it pays to know the boss’s schedule – you’ll be an efficiency fiend.

On top of this, genuinely liking the person you work for can make the world of difference. When we have a boss we don’t like so much, the motivation show up every day and work hard can often be lost. If your boss is a legend, chances are you enjoy heading to work every day. 

CON: You could be accused of being favoured

Nobody likes to be called a suck up, but if your co-workers can clearly see how much extra time you’re spending with your boss, it can cause a bit of drama – especially if they’re catching wind of any potential perks you may be receiving.

Having the reputation of teacher’s pet mightn’t serve you so well when interacting with other colleagues, so it’s important to be cool and upfront about it. Don’t try and hide your relationship with your boss – that’s a bit suss and your co-workers will surely smell a rat.

At the end of the day, it’s always better to be friends than foes when it comes to your boss. There is a way to balance the two worlds, and it’s important to be in the know about what you’re in for and how to bypass the awkwardness.

(Lead Image: 30 Rock) 


Bradley is a writer from Newcastle who enjoys travel, Tina Fey comedies and is a connoisseur of cheap red wine.