Crack the Boss Code

Strategies to get you on your superior’s good side.

Portrait of Tammy Strobel

Strategies to get you on your superior’s good side.

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Imagine if, after slogging your way through school and random jobs, you finally find yourself exactly where you want to be – in a great company doing things you’re passionate about... only to find you have a nightmare boss. It sucks but if you really like this job, you’ll have to learn how to work with them.

Building relationships

“It’s important to balance being competent and supportive, yet not be a threat to your boss,” says Cindy Leong, a relationship coach and an Enneagram practitioner. (Read about the Enneagram personality types on the next page.) But this doesn’t mean suddenly agreeing with your boss on everything (your inner conscience might have a fit and, besides, they’ll know something’s up). The foundation of a good working relationship is not based on a bedrock of a**-kissing. Cindy says it all comes down to understanding where the boss is coming from. “Generally, people will want to collaborate with you if they were to share the same flow of ideas. People (your boss, in this case) would better appreciate you if you can add value to their lives and complement their weaknesses.” In other words, if you want to get along with your boss, you’ll have to spend some time thinking about how to make their lives easier.

Power play

It can often feel like clashes with your boss are personal – especially if you’re particularly passionate about the work you do. You might find some peace if you tell yourself that, at the end of the day, everyone has their reasons for doing what they’re doing. This might mean acknowledging that your boss really has the company’s best interest at heart, or that a disagreement isn’t about you but their own issues. It’s also important not to try to do too much at once. You may risk overstepping boundaries or threatening your boss’ authority and that is definitely not going to get you anywhere. “It’s about taking the time to learn what your boss’s expectations are, his or her working style, and how he or she would prefer to be treated,” says Cindy.

While many strongly believe in the golden rule of “do unto others as you would have them do unto you”, this does not always apply in a work context as personality types may differ. For example, some bosses prefer constant one-on-one communication with staff , while some would largely leave their staff alone so they’ll have the space to do their best work.

Getting ahead with a little compassion

You don’t have to be best friends with your boss – it’s normal that not everyone connects on a personal level. And does gender play a role? Well, maybe, but for Cindy, it’s not the biggest factor. 

“I believe it’s the personality of a person that matters more than the gender,” says Cindy. So put yourself in your boss’ shoes and try to see things from their perspective, and maybe one day, you’ll have a chance to move forward on their recommendation. 


Unlike the Myers-Briggs test, the Enneagram system assumes that a person’s basic personality type does not change over time. However, it’s possible that you’ll have traits found in more than one type. This chart may help you work out what drives your boss (and you too!). 


The rational, idealistic type

Basic Fear: Being corrupt,evil or defective

Basic Desire: To be good, to have integrity, to be balanced

Motivated by: The desire to be right, to improve everything, to be beyond criticism, to be consistent.


The caring, interpersonal type

Basic Fear: Being unwanted and unworthy of being loved

Basic Desire: To feel loved

Motivated by: The need to be loved, to express feelings for others, to be needed and appreciated.


The success-oriented, pragmatic type

Basic Fear: Being worthless

Basic Desire: To feel valuable and important

Motivated by: The desire to be affirmed, to command attention, to be admired, to be regarded as distinguished.


The sensitive, withdrawn type

Basic Fear: Having no identity or significance

Basic Desire: To find themselves and their significance

Motivated by: The need to express themselves and their individuality, to attract a rescuer(It’s rare for this type of person to be a boss!) 


The intense, cerebral type

Basic Fear: Being useless, helpless or incapable

Basic Desire: To be capable and competent

Motivated by: The desire to possess knowledge, to have everything figured out as a way to defend self.


The committed, security-oriented type

Basic Fear: Being without support and guidance

Basic Desire: Security and support

Motivated by: Certainty and reassurance, fight against anxiety and insecurity


The busy, fun-loving type

Basic Fear: Being deprived and in pain

Basic Desire: To have their needs fulfilled and be satisfied

Motivated by: Freedom, happiness and the avoidance of pain 


The powerful, dominating type

Basic Fear: Being harmed or controlled by others

Basic Desire: To protect themselves and be in control of their life and destiny

Motivated by: The need to prove their strength, being important,domination


The easygoing, self-effacing type

Basic Fear: Loss and separation

Basic Desire: To have inner stability and peace of mind

Motivated by: A desire to create harmony and to avoid conflicts and tension

Images Text Lestari Hairul.