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Well that is indeed a well thought out and detailed plan to deal with your ESTJ problem. Since you have pretty much analyzed everything there is about him I don't have much to add. Especially since I am only familiar with INFJ and INTJ so far.

However, if this is a of concern to you, I can "cast the runes" so to speak to see how your interactions with him will go for the rest of the year, what you should look out for; opportunities, pitfalls etc in your interactions with him. That is if you are interested of course. It will help to assess the soundness of your plan, fill in the loopholes and keep you 5 steps ahead of him.
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