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Career Advice

'Yes boss!': Quirky bosses and how to work with them

By Paulo Vargas on July 7, 2015

We all hear about horror stories about terror bosses and their questionable work ethic. But what if you have a competent boss that's just a bit off-kilter? How do you deal with a hippie vegetarian boss or a geeky introvert who's supposed to manage you?

I'm sure you have had your fair share of bosses with quirky personalities. But if not, when you do encounter these bosses, at least you know what to do.

The Jester

He was the class clown back in school, but now he's your boss. He tries to be chummy all the time even when you have deadlines to meet. Whether you're in a meeting or in the elevator, you know a joke is coming. He's like your dad, but you can't just roll your eyes. You actually have to laugh.

There's a reason why your boss is your boss, and that's because he does his job well. The drawback is that you have to endure a barrage of punch lines. Having a joker as a boss will have some downsides but rest assured that you're in good hands. These jesters are great team players and are likely to create a fun environment to get a task done.

They really like getting to know their team and if you find their jokes distracting, unproductive or offensive, try sit down with them and be honest.

He will probably just laugh it off.


The Friend

Most bosses are seasoned pros that have been in the industry for years. But as the millennial generation penetrate the workforce, it's inevitable that some of them will end up as bosses. And age isn't even a factor here. There are bosses that are just naturally friendly.

You eat your lunch together, you grab coffee together, and you even party together. While having a boss as a friend has its perks, you have to realize that he is still your boss. They will give you tasks, they will ask for deadlines, and they will most definitely have off days where they will come off as assholes.

Don't take it personally if, from time to time the friend in them disappears and becomes a boss.


Harvey and Mike from TV show suits. Source: Source:">

The Young-at-heart

Old enough to be your parent, the young-at-heart boss is just as active on social media as you are. They insist on becoming Facebook friends and following you on Twitter. A millennial's nightmare for sure.

This kind of boss is pretty harmless, but be careful accepting their friend request. It means you have to sanitize your online presence a bit: no posting of anything 420 related and no posting of blackout partying pics.

They are pretty reasonable if you tell them that your social media is for family members and close friends, and I'm sure they will understand if you don't "friend" them.

At some point you have to put your foot down and say no to their invitation to check out the band playing at Saguijo.

If you do need them, at least you know they're just a tweet away.


The Activist

Because of your boss, your office is now earth friendly. Everybody recycles and the office is on its way to becoming paperless. He is vegan/vegetarian and has convinced two colleagues to go meat-free. He is the first one to turn the air-conditioning units off. He may or may not have long hair, but definitely wears black sneakers instead of leather shoes.

If their earth-friendly policies are starting to feel like too much evangelization, then tell them politely.

You should not antagonize and at the same time, know yours. You can softly disagree, and I'm sure they will respect your opinion.


The world is full of horrible bosses, but the ones above are not part of that group. If you encounter them, just be glad that despite their quirks, they are still competent enough to do their job. Maybe you can even learn a thing or two from them.