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herding cats 

The phrase herding cats comes from the common saying that something involving coordination of many different groups or people is as difficult as herding cats. One of the commonly encountered uses of the term in technical fields is the phrase "Managing programmers is like herding cats" or "Managing engineers is like herding cats". In education it would be "Managing students is like herding cats". In reality, it would be "Managing cats is like herding cats." It refers to the individualism common in the stereotypical examples of programmers and domesticated cats. A similar phrase, allegedly of Irish origins, is "Minding mice at a crossroads".
Me: Yo. I was having trouble.
You: So, managing cats was like herding cats?
Cats: Ya!
herding cats by catherdmaster January 3, 2009
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Herding cats 

Any difficult activity of uncertain outcome involving numerous and often competing factions that is of dubious value.
The latest project that I'm manging at work involves so many different groups that it's just like herding cats.
Herding cats by eMeS December 22, 2005

herding cats 

Trying to get a group of silly girls/boys in one place to take a silly picture of them.
"I have gotten three other people to agree to do it, but actually getting them in front of the camera is like herding cats."
herding cats by a silly girl July 9, 2006

Herding Cats Phase

The inevitable chaos that one experiences as a projects moves towards the end. The finish line is in sight, there's more loose ends than a 20 year old sweater, everyone is semi-confused and lunging from task to task, and it's an all out assault on the concept of patience.
We've definitely entered the herding cats phase of this project. No idea how we're going to get to completion, hopefully we receive a miracle before someone loses their shit.

like herding cats 

A very difficult task to begin, and even more difficult to complete!
Putting this case together after being cold for twenty years will be like herding cats! All the luck to you Sarge!

hearding cats

Spending endless amounts of effort and while going nowhere
Trying to explain what was needed to support a revenue transaction felt more and more like hearding cats.
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