Brifters on a Reynolds 853 frame is pretty lovely. Lighter than Hi-Ten or Cro-Mo, still comfortable and lively (click the Shwinn in my sig).
I did try out a brand new Specialized Allez cro-mo w/ DT shifters a couple years ago and I almost bought it on the spot. Indexed instead of friction, but other than that, light, comfy and fast. Dunno if Specialized still offer it, but even w/ the lower grade components, it was a blast to ride.
For your boss' old bike, he should throw some clips & straps and a rack to carry picnic lunches.