How To Deal With Your Boss Based On Their Personality-Type

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How To Deal With Your Boss Based On Their Personality-Type

Sometimes getting ahead at your job requires more than being super fantastic at what you do. That doesn’t mean you have to play politics and suck up to the bosses, but it does help to know what their management style is.

Cindy Leong, a relationship coach and Enneagram pratcitioner 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.

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. One system that works to understand your boss is the Enneagram system. This assumes a person’s basic personality type does not change over time, and so you (and your boss) generally have fixed traits. Check out the different types here to figure out what drives your boss.



The Reformer: 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


The Helper: 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 Achiever: 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The Individualist: The sensitive, withdrawn type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



The Investigator: 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 Loyalist: 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



The Enthusiast: 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 Challenger: 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 Peacemaker: 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



This article is featured in CLEO. Written by Karen Fong on 17 October 2017.

Cindy Leong
Cindy Leong
Cindy Leong is a sought after bilingual (English and Mandarin) Enneagram Personality Coach and Corporate Trainer in Asia, who can help you make sense of your professional and personal relationships. She is a member of International Coach Federation (ICF) and Singapore Psychological Society (SPS). Besides a Bachelor Degree in Psychology (majoring in Communications), she also has a Diploma in Business and has done in-depth research and studies in the areas of Organisational Behaviour and Gender Communications, both in Singapore and Taiwan. Through her expertise in corporate executive coaching, personal development, and relationship coaching, she has helped many professionals in their walk through challenging times, particularly in the areas of identity searching, relationship building and career breakthrough. Aside from being a published author of 2 books, she has also been invited by several radio stations and magazines as an expert guest speaker to provide insights into Enneagram, workplace conflicts and relationships.
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