I would think that if the boss knew he was playing with an ex-pro, and the ex-pro tanked the round in order to "suck up" to the boss, that the little exercise might backfire. Most bosses I know got to be bosses because of their competitive spirit. No one likes to lose, but if you know your competition is a rung above you on the talent ladder, and s/he deliberately loses just to make you feel better, you end up really feeling worse. It is different when you are instructing someone; you want to let them feel like they can "beat" you every once in a while, but then the next round you can ratchet up the skill level just a little bit more and the student learns that one victory does not a career make. It kind of depends on the diplomacy skills of the pro. The pro might be just enough "off" of his/her game so that the boss thinks s/he has a chance going into the back nine just to make things equitable, especially if it appears the boss if having an "off" day. (Darn that breeze, it almost made a leaf wiggle!)
By the way, this applies to demonstrating one's skills on a student's guitar, demonstrating one's skills at billiards, or playing chess with a novice. You don't earn points by beating up a rookie.