I don't bother asking about my boss's schedule because he dislikes being asked about it.
こんにちは！
ご質問ありがとうございます。
ご質問について、いくつか言い方が考えられますが、例えば、
I don't bother asking about my boss's schedule because he dislikes being asked about it.
として、『私の上司は予定を聞かれるのが嫌いなので、私も（わざわざ）彼の予定を聞きません。』
My boss doesn't like being asked about his schedule, such as where he's going on his business trip. He seems to dislike it because he feels micromanaged.
として、『私の上司は、どこに出張に行くかなど彼の予定を聞かれるのが好きではありません。管理されているようで嫌みたいです。』とするのはいかがでしょか。
役に立ちそうな単語とフレーズ
micromanage 細かく管理する
参考になれば幸いです。
He never likes to be asked about his schedule, so I don't ask him.
My boss hates it when we ask him where he's going on his business trip, so we never question him about it.
この場合、次のような言い方ができますよ。
ーHe never likes to be asked about his schedule, so I don't ask him.
「彼は予定を聞かれるのが嫌いなので、私も聞かない」
ーMy boss hates it when we ask him where he's going on his business trip, so we never question him about it.
「上司は出張でどこに行くかと私たちに聞かれるのが嫌いなので、私たちもそれについて質問しない」
to go on one's business trip で「出張に行く」
ご参考まで！
日本 
カナダ 
