Dealing with a Difficult Boss

One of the potential hurdles for anyone in the work force is the difficult boss. This is the type of supervisor or boss who always seems to think you're in the wrong or seems generally negative about your work. A difficult boss is hard to work with, and seems impossible to please.

There's a range of possible reasons for a difficult boss:


This type of manager can often be a communications problem, rather than a tyrant. Some managers are just not good communicators. The result is that what sounds like a crossword puzzle to you is what they think is a clear set of instructions.

This sets the scene for the "difficult boss" scenario. It can apply to workplace rules, job instructions, and other basic job functions. Any problems are naturally aggravated by this lack of ability to communicate effectively. They get frustrated, because they're obviously not getting their message across.

So a difficult boss can become an even more difficult boss, trying to correct the problems. Matters aren't helped by the fact that as a teen, you may be considered to be needing to be micro managed all the time. That's a particularly unproductive, irritating, situation. 

The difficult boss with communications problems requires some tactful management. You have to deal with these issues to improve the communications situation and make it clear you're trying to do things properly,

These are the basic rules for communications:

  • Don't argue with the boss directly: It's not a fight you're likely to win. That will achieve nothing, turn the meeting itself into a problem, and just worsen the situation. Talk through the issues, don't dispute them.
  • Always ask questions when you're not sure: Questions show what you know and don't know. That will clarify to the boss your level of understanding, and will also show why the instructions you got weren't understood.
  • When asking about instructions: Ask questions which will get a yes or no answer. It simplifies the whole process. It's important to get your instructions right from the start.

Discipline and Trust

Another common area in which a boss can become a difficult boss is the area of discipline and trust. This type of boss is always conscious of behavior, frequently critical, and sometimes seems to overreact, particularly to the behavior of younger staff. However, in some cases the boss has had experience of real, serious, problems, and the reaction is based on genuine concerns. The problem, as far as you're concerned, is to create some credibility and trust with the manager. You'll notice that some staff are obviously trusted.

To create trust with a difficult boss:

  • Do your job properly: Be seen to be doing a good job, getting things right.
  • Don't do anything which seems likely to upset the boss: Take the hint, play by the rules the boss sets down. Just stay out of the firing line.
  • Ask for advice: The most difficult boss will usually respond to a request for advice, provided it's not something you're already supposed to know. You'll also find out how the boss wants something done, or how to deal with an issue.

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