The Lord asks Satan if he has considered Job; lit. have you put your heart and mind – applied yourself – to Job? It is thus implied that the accuser scrutinises and probes, and that he has detailed knowledge of our lives.
The worst way to approach this book is to look for weaknesses in Job. You start by building up appreciation for him and then you learn from his weaknesses. Job had weaknesses: in his wife and his friends. Satan was aware of that. If we deliberately choose unspiritual friends, it is no surprise if Satan attacks us through them. Satan knows that we tend to forget our besetting sins before we were saved, and so are vulnerable in that area of our lives. He scrutinises for weak moments, tired moments.