Cat owners may instantly recognize the oxymoronic element of the phrase herding kittens, sometimes rendered as herding cats. Cats and kittens are notoriously difficult to wrangle or control, so the idea of herding kittens would naturally sound like an exercise in futility. The concept of bringing order out of chaos or organizing the unorganizable has been compared to the questionable task of herding kittens or cats.
There is a surprising amount of disagreement among etymologists over the origin of the phrase "like herding kittens." Some sources believe the phrase originated in the IT community, where it would be considered difficult to organize a meeting of individual programmers and other independent thinkers. Allegedly, a very senior member of the community who was charged with organizing such a meeting of the minds compared the experience to herding kittens and the phrase became popular among managers and supervisors.
Others claim that the phrase came out of a 1981 MENSA meeting, where some participants wore homemade t-shirts bearing the caption "Organizing MENSA members is like herding kittens (or cats) — just use the right food.", or at least something to that effect. The concept of something difficult or chaotic being similar to herding kittens soon became a popular analogy among those in the know. Other organizations, however, claim that they invented the basic idea of "Organizing (name of group) is like herding kittens" long before the 1981 MENSA meeting.
The phrase has now become shorthand in the business world for taking on a project fraught with chaos and futility. A project manager charged with setting up a meeting of executives from all around the world may very easily compare it to herding kittens. The analogy is especially appropriate when the participants in an organized event are notoriously iconoclastic or resistant to "groupthink." Much like trying to herd kittens in real life, keeping a group of independent thinkers together as a cohesive group or managing several different projects at the same time would be considered by many as an exercise in futility.