Maybe, I think he's going to put pressure on Anna with her career. Take liberties with her whenever she makes a mistake at work.Maybe but Hank is no fool he's a powerful boss with enough resources to get what he wants remembering that now he's at the end of his career so he can do anything with Anna even have a few racy phone calls with her but his way o main focus will be more on work as in the office work trips with Ana or in the mountain house he has are many options.
Presumably he will even deliberately give some important information to the other side.
Only to be able to put more pressure on Anna and finally help her out of her misery by showing her how to save the case after all.
In this way he can bathe in Anna's admiration and gradually make her docile.
Otherwise, I don't see any possibility that Anna willingly, without blackmail, spread her legs for Hank.