It's an interesting suggestion. However I perform execution end of deals (system integration, analytical methodology development, etc.) while he handles the paperwork behind the scenes. If he spends 60 minutes in direct contact with a customer it's amazingly long for him. We also do not have interchangeable skill-sets. As much as I'd like to do the "let's change places for a day" exercise, it just isn't plausible.

I believe I respect him when he says part of his job was particularly challenging and time consuming (like getting contracts executed). I don't particularly feel respected when I say something took a lot of time and effort and get asked, "like what?".

I'm not sure that's a bridgeable gulf.