read someone's mood

I read my boss's mood.

私は上司の顔色をうかがいます

I read my boss's mood carefully.

私は上司の顔色を慎重にうかがいます

I read my boss's mood carefully again and again.

私は上司の顔色を何度も慎重にうかがいます

I read my strict boss's mood carefully again and again.

私は厳しい上司の顔色を何度も慎重にうかがいます

I read my strict boss's mood carefully again and again before offering an opinion.

私は意見を言う前に厳しい上司の顔色を何度も慎重にうかがいます