In a recent job interview for an associate vice president position, a prospective candidate was asked if they had any questions for the search committee. The person asked, “Is this a collaborative environment?” After a pregnant pause that seemed to give birth to triplets, the general response was that the members of the group in that room, all falling somewhere in the middle of the organizational chart, were definitely collaborative among each other, but not so much when moving vertically through the institution’s hierarchy. As one person remarked, “Put us all in a room together and we work well, but with those above us? Well . . .” As the sentence trailed off, the candidate emphasized that they were collaborative, which they had to say, as the alternative would have guaranteed an immediate “vote off the island.” But it was a telling assessment of both the concept of collaboration and its application in our world of academic leadership.