Like many, I don't have any hesitation in questioning (judging?) the wisdom of other people's deals (see, e.g., my comments on Skype). However, as I was reminded the other day, it's a temptation too easy to fall into when you're managing other corporate development professionals.
When you look at someone else's deals on paper, the less-than-ideal terms glare back at you. You want to pick it apart, point out the problems and limitations, but you've got to take into consideration the compromise and negotiation that got the deal where it is. By all means, you don't settle for less than the best deal you can get in the time available. But I know that when I was starting out I didn't like getting second-guessed on terms I'd considered and settled on, and I'm going to work harder to do the same when I'm peering over someone else's shoulder.