Meaning of “herding the cats”

Question

What is the meaning of the phrase herding the cats? I've found one description on Wikipedia but it is not clear enough.

Answer 1

Example:

Last night, after my friends and I finished dinner, we were standing outside the restaurant for ages. Some of us wanted to head to Soho. Some of us wanted to stay nearby. Others wanted to go home. And others were waiting to see what everyone else decided. With everyone so indecisive, keeping the group going was like herding cats.

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).

Answer 2

[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.

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The Washington Post Magazine of 9 June, 1985 is often quoted as the earliest use in print:

At Group L, Stoffel oversees six first-rate programmers, a managerial challenge roughly comparable to herding cats.

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Anecdotal evidence from 2000 offers an origin, with a slightly different meaning:

I first encountered this amusing slogan when I attended the 1981 Mensa Annual Gathering in Louisville, Kentucky. Several of the organizers of the event were wearing custom-made T-shirts that said "Leading Mensans Is Like Herding Cats ...All You Need Is Food." Anyone who has ever been to a Mensa AG would know how apt the phrase is.

But someone else said in 1994:

The original was "Managing professionals is like herding cats." and I adapted it to the quote given above for a button for Jean Cooper when she was first elected to the AMC. Only this past year has it been relegated to lowly MERF t-shirts!

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 think this claim is going to be lost to history because there have already been over two dozen Mensans with unique stories like these each proving that they came up with the quote. At the AG when the quote appeared on T-shirts, even more people came out of the woodwork seriously trying to claim credit for this quote -- many with corroborating witnesses.

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Finally, apparantly German shepherd dogs can successfully herd cats, and Electronic Data Systems made a humorous advert (YouTube) in 2000 showing how tough herding cats might really be.