I've been fortunate to have bosses who don't get upset over upgrades. With few exceptions I prefer not to travel with my colleagues and my friends/family know that if available I will take the upgrade
(I usually give them drink tickets/headphones)
Several years ago I was traveling with my boss to AZ and was running late to the airport. I called my boss enroute and he said that we could just fly out the next morning if neccessary. I told him that I was 10 min away and we should still take the flight. I got to the gate just as they called final boarding. He was in the last row and I had gotten upgraded to first. "He just looked at me and laughed and said it figures" I sent him my ice cream sundae
and went in the chatted in the back with him for a while.
Its a joke with my team that I always get upgraded in airplanes/hotels/car rentals. I have had bosses that if I traveled with I would decline an upgrade simply because of their "issues" I worked for one woman who I tried never to stand next to since she said I was intimidating since I was so much taller than her
