There are two ways: a compassionate way, and a brutal way. How do you feel today?
Hint 2
Before you get to that part, you need to get him to talk to you at all. For that, you need to know his name.
Hint 3
As Lauren, open the drawer of the desk in the office to find an obituary. That's our guy.
Hint 4
As Joey, talk to the ghost about "Allen Reiken's obituary," then "Allen Reiken." Run through the conversation options to get his wretched story.
Hint 5
You now have the options to talk to him about his wife, women in general, or business. This is where you get to choose your approach.
Hint 6
Each subject has two options: either convince him that he has a new opportunity to do better inside the office (in the person of Rosa), or that he's a hopeless loser who deserved what he got.
Hint 7
For example, if you talk about his wife, you can either tell him his wife is inside waiting to talk to him or that he deserved to be abandoned.
Hint 8
If you're feeling compassionate, choose any one of the three subjects (wife, women, or business) and pick the positive option. It's up to Rosa now.