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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!
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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."
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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.
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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!
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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.
Taking charge of a project in such a way that
a) all the participants of the project know their exact roles very well and are ready to hit the ground running when the project gets off the ground and underway
b) the project is completed quickly, efficiently and effectively.
Nancy Pelosi was amazing at playing herd the cats when it came to passing legislation favorable to her.