I know we all dream of having a ‘fun’ and ‘cool’ boss – but have you ever considered that what you want isn’t always what you need?

Let me tell you from experience, the boss who’s so determined to be like and seen as ‘fun’ is usually a bloody nightmare – either because they’re incompetent or they’re using it as a cloaking device for some truly terrible personal traits.

this, but a boss.

Like the boss of mine a few years ago who set about becoming my best friend (like, she asked me to relocate to open a new store for her, promised a rent budget, then just got me to live with her for a few months so we could ‘bond’), then as soon as I agreed to what she wanted me to agree she turned into a narcissistic mess with no separation of work/friendship.

Or this delightful story of a boss who POOPED in lunchboxes and MADE SMALL CAR BOMBS all in the name of ‘fun work pranks’. I am DYING over this!

These are obviously mildly extreme to EXTREMELY extreme examples, but let’s have a look at why even normal levels of wanting to be the fun boss can be a red flag to you as an employee.

A ‘fun’ boss often overpromises

They’re so intent on being liked that they make all kinds of promises around promotions, increased responsibility, or a raise. The thing is, those promises never happen. They’re not just doing it to you either, it’s happening all over the place. Essentially, this is a boss you can’t trust to be honest and realistic with you, so how can you expect to grow in your career?

They often don’t understand differences

A boss who is trying so hard to be your bestie simply can’t comprehend different attitudes towards workplace relationships. It’s actually completely ok to keep friendship and work-life separate but the ‘fun’ boss isn’t able to understand or respect that.

Your lines can get blurred

You’re friends now, so they can call you on the weekends, right? And you can get rip-roaring drunk in front of them and complain about hangovers at work, yeah? It’s also totally ok to unleash your personal problems all over them? No, none of these are smart to do with a boss, no matter how comfortable you are with them. A ‘fun’ boss lulls you into a false sense of security then flip on you when you least expect it.


Their lines can get blurred

As we can see from the lunchbox pooper, workplace pranks are so often such a bad idea because one person’s idea of fun is someone (everyone) else’s nightmare. Jokes at your own expense can also be upsetting, especially coming from a person who has power over you. Heaven forbid the awkward nightmare that can happen when ‘fun’ turns into flirty, even when there’s no intent behind it.

They often can’t give constructive feedback

Constructive is SO important at work if you ever hope to improve. A good boss should never be mean about it, but they should never avoid it either. A ‘fun’ boss is often too worried about how you perceive them to risk ever changing that image. Too often that can result in you being absolutely blind-sided further down the track when they lose patience with problems you never knew were a problem because no-one told you.


It can often lead to favoritism

One of the most important things for a boss is to remain impartial. A ‘fun’ boss will often have obvious favourites, or at least people who appear to be, depending on who chooses to ‘join in the fun’ and who takes a different approach to work life.

Like I said ‘fun’ is more fun in theory than reality when it comes to a boss. Instead, you want a boss who is fair, supportive and challenges you to grow.