So, he’s impressed with your preparation and seems to be wavering. Here are two things that can seal the deal. First of all, suggest a trial period. How can any reasonable person argue with that? Secondly, and this is important: You’ve been carefully reeling him in with your well-laid out scheme, so don’t blow it by asking for your work-at-home day to be a Monday or a Friday. A Tuesday or Wednesday is best -- at least for now.