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Q: I am certain that I am underpaid, given my responsibilities. Unfortunately, doing anything about it requires me to deal with my boss, who is extremely difficult. What can I do?
Focus on the problem, not the person
     No matter how difficult or pleasant your boss, the real issue has to do with the fairness of your compensation.  The more attention you pay to the substantive matters, the less you will be sidetracked by your boss' personality defects.
Listen and learn as much as you advocate
    Chances are your boss will have a strong point of view that he will insists upon stating.  Instead of fighting with your boss over whether that perspective is right, just listen. Once you understand your boss' point of view, and he realizes that you "get it" you can provide your different perspective. If you have taken the time to hear your boss out, he will be more readily grant you the same courtesy.
Do the creative hardwork
     You probably cannot count on your boss to come up with a solution that takes into account with your views as well as his own view or significantly improve the situation by thinking outside the box. So be proactive and get prepared to do this type of creative problem solving for the both of you. As you do, make sure you include your boss' views and input so it feels like a joint problem solving session.
     Even the most difficult people tend to view themselves as fair and therefore want to act in ways that leave others feeling fairly treated.  So as you seek more compensation, stress that is merely an opportunity for the company to treat a valued employee fairly treated. If you can, gather data about what others in similar positions in the company are making and compare those figures to your own salary.
Consider your alternatives
      If your boss is just too nastly, stubborn or useless to deal with directly,  can you  approach another senior manager? Is there someone else who can take up your case for more compensation on your behalf? If so, considering bypassing this difficult person in order to make progress.
Get commitments in writing
     No matter how much progress you make in conversations with your boss, unless those discussions are put in writing you may find it hard to get them enforced.  So, even if all you can get is an exchange of emails, or just a letter from you detailing the points that you agreed upon, get all promises in writing.

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