How to Deal with a Difficult Boss
Understand their motivations: What motivates your boss to be difficult or demanding? By figuring this out, you are able to act accordingly, and hopefully head it off. Perhaps they don’t like to be caught out of the loop by their boss, and like to be updated ASAP on team projects. You can control this and make their life easier by filling them in with regular project updates so that their own manager never catches them unaware.
Anticipate their needs: And be sure to be one step ahead of them. Perhaps traveling to sales meetings gets them stressed out because they like routine and don’t like being out of the office. Make sure to secure their schedule as far in advance as possible, building in extra time for travel, etc. Present it to them ahead of time, prior to them asking for it, to ensure that they are comfortable with it and to allow ample time for tweaks and changes.
Identify triggers: Does your boss flip over misspellings or lateness? These are things that you can (usually) control. Use spell-check AND your own eyes to read and re-read documents that you are sending out on their behalf or ones that they will be copied on. Don’t hesitate to ask a co-worker to proofread your work and let them know you will return the favor. If your boss is a stickler for timeliness, make sure to build an extra 15 minutes or so into your commute.
—Pamela Weinberg, Career Coach