Well, CatchBob! task could be a bit more complex if add new dimensions like in the sheepdog trial:

Sheepdog trial (or simply dog trial) is a competitive dog sport in which herding dog breeds move sheep around a field, fences, gates, or enclosures as directed by their handlers. Such events are particularly associated with hill farming areas, where sheep range widely on largely unfenced land. These trials are popular in the United Kingdom, Ireland, Canada, the USA, Australia, New Zealand and other farming nations.

Different scenarios are possible:

There are several events, but the key element is the control of three to six sheep by one or two highly trained dogs under the control of a single shepherd. Both time and obedience play a part, as competitors are penalised if a sheep strays from the prescribed course.

One event consists of having the dog send three sheep up a steep hill through three or more gates. The shepherd must stand at the bottom of the hill and direct the dog by whistling. The huntaway dog barks loudly to push the sheep ahead up the hill.

Another popular event involves having the dog split six sheep into two groups of three and conducting each group in turn to small pens through a defined course by heading dogs. The group not being led is guarded by one of the two dogs, an eye-dog (from its ability to keep the sheep still by head movement alone). This is more difficult than it sounds, as the sheep invariably try to stay together.