I would divide this into two parts: general good practice when dealing with bosses, and dealing with problem bosses.
First there’s communication style
– Ideally you would tailor your communication style so that they find you easy to deal with, perhaps even like you! Are they in a hurry and wanting a quick summary or are they a thoughtful, detail person?
– Make sure you don’t become high maintenance. Don’t take up too much of their time, don’t check everything with them before you do it (unless they want that!), don’t send them big long reports or emails to read, don’t phone them at times when they are busy or tired or thinking about something else.
– Don’t always come with bad news and problems
Then there’s influencing –
a) what’s in it for them, what do they want or need? They have weaknesses too, if you think about it – they need to you help them and do things that aren’t totally in your job description, maybe do longer hours every now and then, they need you to stay motivated in order for you to be creative and work hard, they need to look good to their peers and superiors, they don’t know all the answers so they need your help, etc), and…
b) what style of influencing is best for them? This depends on the type of person they are – are they influenced by facts and logic or by emotions and excitement? Are they risk-averse or are they impulsive and brave?
As bosses become more difficult then the main principles of assertiveness also apply to bosses as well as anyone else – use the 4 step process which is to
1) Understand their situation and say that you do,
2) Say how you feel (worried about letting the side down, feeling demotivated because you don’t have enough effect on performance of the job, etc, so not whingeing or negative but still concerned and not completely happy – this is a powerful second step since they can’t ignore it), then
3) what you want to happen – this makes it easier for them since you are giving them a solution, and makes you look positive, and
4) asking them if they agree, can they see your point of view, is the request reasonable – this commits them to a solution, and enables you to find out if there is any resistance in order to be able to handle it if necessary.
But if your boss is really bad, (as in psychotic / psychopathic / damaged / sadistic / useless, etc, and there are lots of these about), then there are only three options:
• train your boss to behave better, using the four step process described above (may take repetition and persistence!)
• leave (there’s always another job out there, you have to believe you’re worth of it, and there’s no harm in looking. The times I’ve been pushed I’ve looked back and thought I should have jumped ages earlier! If I had just had the courage!
• cease to care … and they should be done in that order – doing a job you don’t care about is the worst outcome! If this happens they’ve won and you’ve lost.