Speaking of contradictory orders ... Or is it that the chief, as a professional, worthless? This should be checked. Just do not force events and do not expose the boss a fool at every opportunity and an awkward case. It may be that in terms of relationships "superior-subordinate" he is not a fool, and is well aware what all these seemingly innocent questions specialty.
But a responsible annual meeting with senior management you need to be fully prepared. It is desirable that by the time you began a friendly relationship with your boss Secretary (of either sex) who have access to the papers of his boss. No, you do not need to substitute some documents or edit the report. It is enough to get acquainted with the general direction of thought leaders and find out where in the report and the report are the most vulnerable places. And prepare an alternative report, without gaps or spaces. And send it by e-mail or fax the Chief General Manager - a piece of cake. As a minimum, a pale appearance to your immediate boss will be provided.
Not a bad option - to give, as they say, with hands and feet the head of your "brilliant" idea (and in fact empty and worthless), presenting it as if it is only your great boss can cope with it. The idea, meanwhile, must be powerful enough to have the boss did not have even a shadow of suspicion on her account until such time until it is too late. Maybe he, for the long and painful (for you) the years of his leadership in something already started to understand. In this situation, you will just have to wait until his work finally come to a halt, so much so that his inaction is interested not only the team, but his immediate superior.
You can certainly use natural and human weaknesses that may exist and your boss. Or are not available. So Long. In other words, make the hitherto respectable citizen and the chief began to perceive as an incorrigible womanizer, a violent alcoholic, or even demonic cult follower. Just lay a "tangible evidence" his boss must be skillfully. And it is desirable that they are, somehow, caught the eye of immediate supervisors your boss before they are discovered by him.
Information even before the Information Age has always been formulated and mixed, and even more so in the women's team, good. Sent to all collage, where chef melts into the arms of her boyfriend on the gay party, and be able to novice Internet user. Of course, everyone will understand that it is - a joke. But osadochek remain.