Please imagine, your boss, always does not listen to the others advices or ideas, asks you to do a task and you find that there are many many technical issues. What will you do?
Option 1: Tell him/her directly? Your boss will reject your point and just says "Technical issue is not a real issue, there is one and only one issue in the world - COST! Don't tell me any excuse!!"
Option 2: Try your best to do the task? You have to put a lot of efforts and finally you produce nothing useful, and you boss will shout to you and believe that you are an useless employee.
If you are unlucky, your boss will ask you to do something impossible. For instance, the system manager asks the project manager to make a project plan and risk analysis for an integration of two individual systems and these two systems are maintained by two different vendors. However, all of staffs know that this project plan and risk analysis should cost over ten millions HK dollors!! The salary of a project manager is just ony fifty thousands dollors. How can a project manager fullfill the requirement of the planning and analysis? It is totally impossible!! But, we have no choice to reject the request from the key stakeholder. What he/she can do is proving what the boss thinks is wrong...
"If you cannot change your environment, you should change your attitude.", but when your boss pressures more and more into you, the only thing you against the boss is to quit the job...