At some point in everyone’s career you will encounter what I call the “difficult or extreme boss”. Make no mistake about it, we are not talking about a boss that tries to get the best out of you, these are the people whose behavior or personality type places the people who work for them in what could be described as no win situations which can be profoundly disruptive for the workplace. While they can take many forms today I’m going to focus on two dominate types that I call “The Long Timer”, and “The Controller”. Their approach may be different but the resulting frustration and loss of morale is the same for the people who work for them.
The Long Timer
The long Timer is someone who has been promoted based on connections, family ties, or simply because they have managed to survive for a considerable amount of time in the system. They generally don’t make waves so there is never really a reason to fire them and they get promoted by default based on the reasoning “John has been here for a long time, he deserves a shot.” Eventually they reach a level of complete incompetence and generally do not know how to perform their jobs. You can expect them to resist any fresh ideas or they can be counted on to steal as their own, anything that the people under them present.
Working for a Long Timer can be frustrating because you can expect to receive little if any guidance, direction, or support. And, over time you begin to resent this person because nothing is ever clear unless you make a mistake that brings attention to them.
Manage “UP”
The trick is to manage UP with the long timer and provide what they desire the most: Your admiration and respect. To some degree they do deserve it, because they have done something right and managed to survive for quite a long time. If you let them know you want to make them look good, you’ll generally find they will work with you. However, if there is any hint that you look down on them, they will block you on every turn. Their position as a long time member of the company means they WILL win.
Present an idea or proposal to them with phrases like: I knew YOU would appreciate this, or, I thought this would work because it allows YOU to… By using this approach you now have ultimate freedom and simply have to sell the idea UP along with giving them part of the credit for YOUR idea. This does mean having to spend some time getting to know the Long Timer to understand what makes them tick. But it will pay dividends because the less threatened the Long Timer feels, the more you will be able to move your ideas forward.
One final word of caution however, the Long Timer knows how to take credit and also how to deflect blame. They are prone to use those around them as scapegoats, so be prepared for a few arrows in your back… Nothing personal, it’s just business!
The Controller
The second difficult boss, The Controller, may be the most extreme: They can be bright very driven people, who are at first friendly and welcoming; but long term, their goal is to let you know that the department they run is THEIR show and they require a good deal of admiration and above all CONTROL.
These are the people who tend to suck up all the air in a room telling you about their accomplishments and open door policies. They are the classic micro-managers because in their minds THEY know how things should go and delegation is not something upon which they look kindly.
They maintain their grip on power by cutting off ideas at the knees if they didn’t come from them and tend to be great manipulators. Working for a controller can sometimes be soul crushing because their biggest weapons are undermining your decision making and finding fault. No matter how dazzling your report or presentation, they will find the misspelled word and that small error becomes all consuming. Most employees find them un-pleasable because they will always have done it differently or will find some fault no matter how well you have followed their direction.
Controllers are demanding to the Nth degree and have no problem asking you to work weekends or crowding into your personal time. The lead character in “The Devil Wears Prada ”immediately comes to mind. New hires fall prey to this 
tactic thinking they are making a good impression and fail to realize this is standard operating procedure.
Controller Emotional Stages
Employees tend to go through a three stage process with The Controller of first engagement and hard work; second, realizing that nothing is ever quite good enough; and finally becoming discouraged and frustrated. If you find yourself continually repeating conversations you’ve had with them or their names keep coming up in your conversations with friends, you are probably dealing with a Controller. The key give away of a Controller is the fact that turn over is high in their department because this person is so controlling and demeaning that people come and go at a fairly rapid rate.
Use of your support system
Unlike the Long Timer it’s difficult to manage The Controller because total submission is simply not enough. You will have to constantly remind yourself that you have performed well in the past and if there are supportive people you can turn to by all means do! I say that because one of the main results of dealing with a difficult boss like The Controller is that they undermines your confidence and self esteem. It is reassuring to have someone to confide in to refute the continual attacks coming your way. Your support system can serve to boost your confidence and let you know it is not you but your situation, which is very important. They are also a good resource for information on how they may have handled a similar situation in the past.
You will have to develop your own inner level of appreciation for a job well done while in your position. In other words look around for contacts that provide information for comparison so that you know realistically where your work falls. And don’t forget to take stress reducing breaks or sign up for a gym membership to work off the frustration while you begin circulating an updated resume.
I hope I’ve given you enough detail to determine if your work really is fine and help you see that your current difficulties maybe more situational rather than a drop in your abilities.
These suggestions will not correct the tough situation of dealing with someone who on a daily basis makes your life a living nightmare, but use the tactics where it seems appropriate to help you weather the storm. Listen to the podcast to hear this program in it’s entirety.