I’ve come across many folks in my career who often crib about having a Boss who is hard to please. Sometimes this leads to deep anxiety or rather insecurity if you’ve a peer who is good at managing his boss.
You've heard managers say they'll heap riches on those who do a good job. Ignore their words; watch their actions. Who do they really reward? Why? Mostly, we reward those who meet our needs, first and foremost. If you know what your managers really want, you can meet their needs while meeting the needs of the business. The late Harvard psychology professor David McClelland had an easy framework you can use.
McClelland said motivation comes in three flavors: power, affiliation, and achievement. Power People want things to happen their way. Affiliation People want to be popular and liked. And Achievement People want results. We're all part power, part affiliation, and part achievement.
If your boss wants you to get results, my advice on "working smart" holds. Get stuff done. Measure what you get done. Discuss the measures with your boss. Do, do, do. Your boss will be thrilled that by working smart, you can get more stuff done in less time. Then go home early, and have a life.
If your bosses want power, they want things done their way. Like bureaucrats, Power bosses often work this way. Following procedure and doing things the right way is more important than doing the right things.
Your job for a Power boss is helping her empire-build and/or helping her get things done her way. Be careful, though. Your boss may be bad at figuring out what needs to be done. So even if she's getting her way, her way just might hurt the business.