Difficult bosses
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We’ve all met them. Many of us have worked for them. I call them The Bully Boys. They rule by fear, not reason. They destroy the lives of those who work for them. In the end they ruin their own personalities. And when they do our human nature gets the better of us and we rejoice.
We shouldn’t. Rejoicing at the downfall of anyone is bad but rejoicing at the demise of a Bully Boy is worse. They are to be pitied more than hated. You see, they are inadequate people, insecure, unhappy, unbalanced. If the world seems to have dealt them a good hand it is a false observation. The world is laughing at them because they have been fooled, pocketed in a trap called power, wound in a coat called wealth.
How can we deal with them when they are so deluded that they think they rule us?
Not by overt fighting, that’s for sure. A head-to-head will leave you bruised and them, even more deluded than they already are. Our approach has to be more subtle than force. And its objective must be to win – and to get them winning, too. You do not kill a sick man, you help him recover. Here’s a five point plan for dealing with the difficult boss.
- Set your mind on his problem. He or she is a sad, lonely person, adrift on a choppy sea without friends willing to come to the rescue. He needs you. Be prepared to help, whatever the effort required.
- Study his behaviour, not in a critical, bemoaning way but objectively, analytically. Try to see the world from his point of view. How much does he listen, how much does he talk? Can you see when he is thinking deeply about the business? How much does he care about the business? Can you see anything in his behaviour that tells you what he really enjoys? What improvement in the business would make him happy? Look especially for the good points about him. If you think there are none, you are wrong. Nobody is wholly evil. Make a note of your observations about him. Do not make it a critical log of bad characteristics; make it a balanced record of pros and cons. Do this part of your work thoroughly. Knowledge is your most important weapon.
- Ask yourself how you could improve the business. It doesn’t matter if your idea is something small – in fact, at the outset don’t look for major suggestions, find little, useful improvements that he could make and of which he could be proud. Ask him if you could have his views about an idea you have. Don’t tell him his job, ask his opinion.
- Remember that he is going to get the credit for what you suggest. Don’t get irritated by that. If it was your idea, you will know it. Nobody else needs to – yet. Keep feeding him ideas, gradually introducing bigger issues from which the business will benefit. It will soon be obvious to everyone that the ideas are coming from you. Businesses have no secrets. Your stature will grow. He will start to talk to you.
- Persevere. You may think the suggestions I have made won’t succeed. They will if you keep working at them. I have practiced this way of dealing with difficult bosses four times in my business life. It worked three out of the four times. Why not the fourth? Because I was too pushy. If I had set about it less aggressively, then it would have worked that time as well.
Let me know how you get on.

antony sutch
How right. We get the best out of people if we support and build them up. Everyone is looking for love in the end. Note Alain de Botton,s thoughts in Anxiety Status. Also we must not become bullies ourselves. What we do to others effects us also.
darja dezman
What a great stuff John. We really are not supposed to always only relay on our points of view. Instead we are also challenged to pretend we are somebody else, like our boss for example. Considering that, our life becomes quite different then.
johnbittleston
Thank you Darja. Always good to have your input.
John
LU Keehong
Dear John
I always hold the view that there is NO difficult person but a person with difficulties.
When his or her difficulties are NOT recognized or resolved with others’ help or through the facilitation of others, he or she become difficult.
At the same time, I have an exception – a person with NO integrity.
In your article you mentioned a Bully Boss, or supersivor, since I do not subscribe to the ‘boss-subordinate’ relationship, so I am not sure if my approach still hold true?
Any input on this?
With warm regards
LU Keehong Mr.