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Overseers occupied a curious niche in the antebellum economy. They tended to be aspiring planters who came from the lower rungs of white society, hoping to work their way into a position of respectability. An overseer might own a few slaves of his own, especially if he worked on one of the larger plantations where pay was better and the scope of the work necessitated a degree of intelligence and literacy. A good overseer was key to a functioning plantation because the planter was rarely involved day to day affairs if he visited at all. Whether the owners' relatives were involved depended on the economic circumstances of the family. Younger sons often helped out on the farm until they left to attend universities in the Northeast or Europe.

Planters with holdings that merited a full-time overseer were actually a small percentage of the population. There are records of mid-size slaveholders debating whether or not to hire one, with the position more common in South Carolina or the Old Southwest than the areas where yeoman farmers were more common. When it came time to hire, Fanny Kemble's Journal of a Residence on a Georgian Plantation gives a glimpse of how the process worked. She wrote that the outgoing overseer had spent a number of years “personally governing, without any assistance whatever, seven hundred people [i.e. slaves] scattered over three large tracts of land, at a considerable distance from each other.” The replacement who arrived had spent fourteen years living with another planter, whose slaves Kemble reports were treated well. This kind of longterm, stable experience was outside the norm, but it shows the kind of networks people built over time, just like any hiring process. Less generous descriptions of overseers come from the likes of Frederick Law Olmsted, who reported in The Cotton Kingdom (a reprint of his dispatches for The New York Times) that the overseer was “a young man, very dirty and sweaty, with a ragged shirt and no coat on” who “was surly and rude in his actions” and occupied a position of disdain. Friction between an overseer and his boss was common.

The most unusual arrangement was when the planter either performed the function himself out of disgust with a former overseer or had a slave fill the position. Jefferson Davis was famous for his relationship with James Pemberton, who oversaw most of his holdings. More commonly the slaves beneath the overseer were divided into teams, with a driver at the head of each team who was responsible for enforcing discipline. There would be a head driver, who in turn reported to the white overseer, who was the master for all intents and purposes while the owner was away. The arrangement on the Butler plantation is described in some detail in Kemble's journal.