I always go prepared for anything, so I pack a basic set of lights, reflectors, and then we get to his office and it's literally so tiny, that when I try a single strobe light, it takes up half of the space(it's one of my smaller ones too!).
Luckily there was a nice large window, so we do a little rearranging and I have him sit on the couch with me on on the other end. I use my reflector, we're giggling throughout because it's all so funny and I get the shot he and I were both looking for.