What is the meaning of the phrase herding the cats? I've found one description on Wikipedia but it is not clear enough.
You use the expression to refer to a failure of a collection of people to behave, or be led, as a united whole. The idea behind the expression is that cats aren't herd animals, so you're trying to elicit a behaviour from creatures incapable of it.
Note that there's no the: it's herd cats (not herding the cats).
[Doing something] is like herding cats refers to any activity which is extremely difficult and quite possibly futile, suggesting their are wildly unpredictable forces at play.
It's most often used when referring to managing a given group of people, especially programmers, or managing a software project.
The Washington Post Magazine of 9 June, 1985 is often quoted as the earliest use in print:
Anecdotal evidence from 2000 offers an origin, with a slightly different meaning:
But someone else said in 1994:
The first may be incorrect, because, as far I can tell, Jean Cooper was elected in the early 1990s. This second may also be incorrect, according to a reply:
I am reading Willa Cather's Death Comes for the Archbishop, original copyright 1927. In Book 5, Chapter 2, she quotes a priest who complains that he is always sent "a fouetter les chats." My cursory investigation of the translation of the phrase makes me wonder if it is indeed "herding cats," and whether the phrase has an earlier provenance than current business practices recognize.